# Oakland (OAK) to Chicago (ORD)

Lowest published fares for the months ahead: $204 round trip, Axel-exclusive, Frontier Airlines, 1 stop, Jan 7–10, 2027; $109 one way, Axel-exclusive, Frontier Airlines, 1 stop, Jan 5, 2027; 144 priced flights on 72 exact dates, 1 adult, economy, checked Oct 29, 2026. Flights for 1 adult in economy. Prices are total for all travelers in USD, including required taxes. Basic economy may apply.

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### Oakland (OAK) to Chicago (ORD): November 2026

| Travel dates | Airline | Stops | Total price |
| --- | --- | --- | ---: |
| Nov 19, 2026 – Nov 22, 2026 · 3 nights · [Compare return dates departing Nov 19, 2026](https://helloaxel.com/en/flights/choose/oak-ord/nov-19) | Frontier Airlines | Up to 1 stop each way | [Axel-exclusive $252.63](https://helloaxel.com/en/f/start/from/oak/to/ord/depart/november-19-2026/return/november-22-2026/adults/1/cabin/economy) |
| Nov 19, 2026 – Nov 22, 2026 · 3 nights · [Compare return dates departing Nov 19, 2026](https://helloaxel.com/en/flights/choose/oak-ord/nov-19) | Alaska Airlines | Up to 1 stop each way | [Axel-exclusive $411.25](https://helloaxel.com/en/f/start/from/oak/to/ord/depart/november-19-2026/return/november-22-2026/adults/1/cabin/economy) |
| Nov 20, 2026 – Nov 23, 2026 · 3 nights · [Compare return dates departing Nov 20, 2026](https://helloaxel.com/en/flights/choose/oak-ord/nov-20) | Frontier Airlines | Up to 1 stop each way | [Axel-exclusive $252.63](https://helloaxel.com/en/f/start/from/oak/to/ord/depart/november-20-2026/return/november-23-2026/adults/1/cabin/economy) |
| Nov 20, 2026 – Nov 23, 2026 · 3 nights · [Compare return dates departing Nov 20, 2026](https://helloaxel.com/en/flights/choose/oak-ord/nov-20) | Alaska Airlines | Up to 1 stop each way | [Axel-exclusive $411.25](https://helloaxel.com/en/f/start/from/oak/to/ord/depart/november-20-2026/return/november-23-2026/adults/1/cabin/economy) |
| Nov 21, 2026 – Nov 28, 2026 · 7 nights · [Compare return dates departing Nov 21, 2026](https://helloaxel.com/en/flights/choose/oak-ord/nov-21) | Frontier Airlines | Up to 1 stop each way | [Axel-exclusive $290.26](https://helloaxel.com/en/f/start/from/oak/to/ord/depart/november-21-2026/return/november-28-2026/adults/1/cabin/economy) |
| Nov 21, 2026 – Nov 28, 2026 · 7 nights · [Compare return dates departing Nov 21, 2026](https://helloaxel.com/en/flights/choose/oak-ord/nov-21) | Alaska Airlines | Up to 1 stop each way | [Axel-exclusive $472.50](https://helloaxel.com/en/f/start/from/oak/to/ord/depart/november-21-2026/return/november-28-2026/adults/1/cabin/economy) |
| Nov 24, 2026 · One way · [Compare return dates departing Nov 24, 2026](https://helloaxel.com/en/flights/choose/oak-ord/nov-24) | Frontier Airlines | Up to 1 stop each way | [Axel-exclusive $155.25](https://helloaxel.com/en/f/start/from/oak/to/ord/depart/november-24-2026/trip/one-way/adults/1/cabin/economy) |
| Nov 24, 2026 · One way · [Compare return dates departing Nov 24, 2026](https://helloaxel.com/en/flights/choose/oak-ord/nov-24) | Alaska Airlines | Up to 1 stop each way | [Axel-exclusive $249.75](https://helloaxel.com/en/f/start/from/oak/to/ord/depart/november-24-2026/trip/one-way/adults/1/cabin/economy) |
| Nov 24, 2026 – Nov 29, 2026 · 5 nights · [Compare return dates departing Nov 24, 2026](https://helloaxel.com/en/flights/choose/oak-ord/nov-24) | Frontier Airlines | Up to 1 stop each way | [Axel-exclusive $290.26](https://helloaxel.com/en/f/start/from/oak/to/ord/depart/november-24-2026/return/november-29-2026/adults/1/cabin/economy) |
| Nov 24, 2026 – Nov 29, 2026 · 5 nights · [Compare return dates departing Nov 24, 2026](https://helloaxel.com/en/flights/choose/oak-ord/nov-24) | Alaska Airlines | Up to 1 stop each way | [Axel-exclusive $472.50](https://helloaxel.com/en/f/start/from/oak/to/ord/depart/november-24-2026/return/november-29-2026/adults/1/cabin/economy) |
| Nov 26, 2026 – Nov 29, 2026 · 3 nights · [Compare return dates departing Nov 26, 2026](https://helloaxel.com/en/flights/choose/oak-ord/nov-26) | Frontier Airlines | Up to 1 stop each way | [Axel-exclusive $290.26](https://helloaxel.com/en/f/start/from/oak/to/ord/depart/november-26-2026/return/november-29-2026/adults/1/cabin/economy) |
| Nov 26, 2026 – Nov 29, 2026 · 3 nights · [Compare return dates departing Nov 26, 2026](https://helloaxel.com/en/flights/choose/oak-ord/nov-26) | Alaska Airlines | Up to 1 stop each way | [Axel-exclusive $472.50](https://helloaxel.com/en/f/start/from/oak/to/ord/depart/november-26-2026/return/november-29-2026/adults/1/cabin/economy) |
| Nov 27, 2026 – Nov 30, 2026 · 3 nights · [Compare return dates departing Nov 27, 2026](https://helloaxel.com/en/flights/choose/oak-ord/nov-27) | Frontier Airlines | Up to 1 stop each way | [Axel-exclusive $290.26](https://helloaxel.com/en/f/start/from/oak/to/ord/depart/november-27-2026/return/november-30-2026/adults/1/cabin/economy) |
| Nov 27, 2026 – Nov 30, 2026 · 3 nights · [Compare return dates departing Nov 27, 2026](https://helloaxel.com/en/flights/choose/oak-ord/nov-27) | Alaska Airlines | Up to 1 stop each way | [Axel-exclusive $472.50](https://helloaxel.com/en/f/start/from/oak/to/ord/depart/november-27-2026/return/november-30-2026/adults/1/cabin/economy) |
| Nov 28, 2026 – Dec 5, 2026 · 7 nights · [Compare return dates departing Nov 28, 2026](https://helloaxel.com/en/flights/choose/oak-ord/nov-28) | Frontier Airlines | Up to 1 stop each way | [Axel-exclusive $252.63](https://helloaxel.com/en/f/start/from/oak/to/ord/depart/november-28-2026/return/december-5-2026/adults/1/cabin/economy) |
| Nov 28, 2026 – Dec 5, 2026 · 7 nights · [Compare return dates departing Nov 28, 2026](https://helloaxel.com/en/flights/choose/oak-ord/nov-28) | Alaska Airlines | Up to 1 stop each way | [Axel-exclusive $411.25](https://helloaxel.com/en/f/start/from/oak/to/ord/depart/november-28-2026/return/december-5-2026/adults/1/cabin/economy) |

### Oakland (OAK) to Chicago (ORD): December 2026

| Travel dates | Airline | Stops | Total price |
| --- | --- | --- | ---: |
| Dec 1, 2026 · One way · [Compare return dates departing Dec 1, 2026](https://helloaxel.com/en/flights/choose/oak-ord/dec-1) | Frontier Airlines | Up to 1 stop each way | [Axel-exclusive $115.00](https://helloaxel.com/en/f/start/from/oak/to/ord/depart/december-1-2026/trip/one-way/adults/1/cabin/economy) |
| Dec 1, 2026 · One way · [Compare return dates departing Dec 1, 2026](https://helloaxel.com/en/flights/choose/oak-ord/dec-1) | Alaska Airlines | Up to 1 stop each way | [Axel-exclusive $185.00](https://helloaxel.com/en/f/start/from/oak/to/ord/depart/december-1-2026/trip/one-way/adults/1/cabin/economy) |
| Dec 3, 2026 – Dec 6, 2026 · 3 nights · [Compare return dates departing Dec 3, 2026](https://helloaxel.com/en/flights/choose/oak-ord/dec-3) | Frontier Airlines | Up to 1 stop each way | [Axel-exclusive $215.00](https://helloaxel.com/en/f/start/from/oak/to/ord/depart/december-3-2026/return/december-6-2026/adults/1/cabin/economy) |
| Dec 3, 2026 – Dec 6, 2026 · 3 nights · [Compare return dates departing Dec 3, 2026](https://helloaxel.com/en/flights/choose/oak-ord/dec-3) | Alaska Airlines | Up to 1 stop each way | [Axel-exclusive $350.00](https://helloaxel.com/en/f/start/from/oak/to/ord/depart/december-3-2026/return/december-6-2026/adults/1/cabin/economy) |
| Dec 4, 2026 – Dec 7, 2026 · 3 nights · [Compare return dates departing Dec 4, 2026](https://helloaxel.com/en/flights/choose/oak-ord/dec-4) | Frontier Airlines | Up to 1 stop each way | [Axel-exclusive $215.00](https://helloaxel.com/en/f/start/from/oak/to/ord/depart/december-4-2026/return/december-7-2026/adults/1/cabin/economy) |
| Dec 4, 2026 – Dec 7, 2026 · 3 nights · [Compare return dates departing Dec 4, 2026](https://helloaxel.com/en/flights/choose/oak-ord/dec-4) | Alaska Airlines | Up to 1 stop each way | [Axel-exclusive $350.00](https://helloaxel.com/en/f/start/from/oak/to/ord/depart/december-4-2026/return/december-7-2026/adults/1/cabin/economy) |
| Dec 5, 2026 – Dec 12, 2026 · 7 nights · [Compare return dates departing Dec 5, 2026](https://helloaxel.com/en/flights/choose/oak-ord/dec-5) | Frontier Airlines | Up to 1 stop each way | [Axel-exclusive $215.00](https://helloaxel.com/en/f/start/from/oak/to/ord/depart/december-5-2026/return/december-12-2026/adults/1/cabin/economy) |
| Dec 5, 2026 – Dec 12, 2026 · 7 nights · [Compare return dates departing Dec 5, 2026](https://helloaxel.com/en/flights/choose/oak-ord/dec-5) | Delta Air Lines / Frontier Airlines | Up to 1 stop each way | [Axel-exclusive $302.50](https://helloaxel.com/en/f/start/from/oak/to/ord/depart/december-5-2026/return/december-12-2026/adults/1/cabin/economy) |
| Dec 8, 2026 · One way · [Compare return dates departing Dec 8, 2026](https://helloaxel.com/en/flights/choose/oak-ord/dec-8) | Frontier Airlines | Up to 1 stop each way | [Axel-exclusive $115.00](https://helloaxel.com/en/f/start/from/oak/to/ord/depart/december-8-2026/trip/one-way/adults/1/cabin/economy) |
| Dec 8, 2026 · One way · [Compare return dates departing Dec 8, 2026](https://helloaxel.com/en/flights/choose/oak-ord/dec-8) | Alaska Airlines | Up to 1 stop each way | [Axel-exclusive $185.00](https://helloaxel.com/en/f/start/from/oak/to/ord/depart/december-8-2026/trip/one-way/adults/1/cabin/economy) |
| Dec 10, 2026 – Dec 13, 2026 · 3 nights · [Compare return dates departing Dec 10, 2026](https://helloaxel.com/en/flights/choose/oak-ord/dec-10) | Frontier Airlines | Up to 1 stop each way | [Axel-exclusive $215.00](https://helloaxel.com/en/f/start/from/oak/to/ord/depart/december-10-2026/return/december-13-2026/adults/1/cabin/economy) |
| Dec 10, 2026 – Dec 13, 2026 · 3 nights · [Compare return dates departing Dec 10, 2026](https://helloaxel.com/en/flights/choose/oak-ord/dec-10) | Alaska Airlines | Up to 1 stop each way | [Axel-exclusive $350.00](https://helloaxel.com/en/f/start/from/oak/to/ord/depart/december-10-2026/return/december-13-2026/adults/1/cabin/economy) |
| Dec 11, 2026 – Dec 14, 2026 · 3 nights · [Compare return dates departing Dec 11, 2026](https://helloaxel.com/en/flights/choose/oak-ord/dec-11) | Frontier Airlines | Up to 1 stop each way | [Axel-exclusive $215.00](https://helloaxel.com/en/f/start/from/oak/to/ord/depart/december-11-2026/return/december-14-2026/adults/1/cabin/economy) |
| Dec 11, 2026 – Dec 14, 2026 · 3 nights · [Compare return dates departing Dec 11, 2026](https://helloaxel.com/en/flights/choose/oak-ord/dec-11) | Alaska Airlines | Up to 1 stop each way | [Axel-exclusive $350.00](https://helloaxel.com/en/f/start/from/oak/to/ord/depart/december-11-2026/return/december-14-2026/adults/1/cabin/economy) |
| Dec 12, 2026 – Dec 19, 2026 · 7 nights · [Compare return dates departing Dec 12, 2026](https://helloaxel.com/en/flights/choose/oak-ord/dec-12) | Frontier Airlines | Up to 1 stop each way | [Axel-exclusive $258.00](https://helloaxel.com/en/f/start/from/oak/to/ord/depart/december-12-2026/return/december-19-2026/adults/1/cabin/economy) |
| Dec 12, 2026 – Dec 19, 2026 · 7 nights · [Compare return dates departing Dec 12, 2026](https://helloaxel.com/en/flights/choose/oak-ord/dec-12) | Alaska Airlines | Up to 1 stop each way | [Axel-exclusive $420.00](https://helloaxel.com/en/f/start/from/oak/to/ord/depart/december-12-2026/return/december-19-2026/adults/1/cabin/economy) |
| Dec 15, 2026 · One way · [Compare return dates departing Dec 15, 2026](https://helloaxel.com/en/flights/choose/oak-ord/dec-15) | Frontier Airlines | Up to 1 stop each way | [Axel-exclusive $115.00](https://helloaxel.com/en/f/start/from/oak/to/ord/depart/december-15-2026/trip/one-way/adults/1/cabin/economy) |
| Dec 15, 2026 · One way · [Compare return dates departing Dec 15, 2026](https://helloaxel.com/en/flights/choose/oak-ord/dec-15) | Alaska Airlines | Up to 1 stop each way | [Axel-exclusive $185.00](https://helloaxel.com/en/f/start/from/oak/to/ord/depart/december-15-2026/trip/one-way/adults/1/cabin/economy) |
| Dec 17, 2026 – Dec 20, 2026 · 3 nights · [Compare return dates departing Dec 17, 2026](https://helloaxel.com/en/flights/choose/oak-ord/dec-17) | Frontier Airlines | Up to 1 stop each way | [Axel-exclusive $258.00](https://helloaxel.com/en/f/start/from/oak/to/ord/depart/december-17-2026/return/december-20-2026/adults/1/cabin/economy) |
| Dec 17, 2026 – Dec 20, 2026 · 3 nights · [Compare return dates departing Dec 17, 2026](https://helloaxel.com/en/flights/choose/oak-ord/dec-17) | Alaska Airlines | Up to 1 stop each way | [Axel-exclusive $420.00](https://helloaxel.com/en/f/start/from/oak/to/ord/depart/december-17-2026/return/december-20-2026/adults/1/cabin/economy) |
| Dec 18, 2026 – Dec 21, 2026 · 3 nights · [Compare return dates departing Dec 18, 2026](https://helloaxel.com/en/flights/choose/oak-ord/dec-18) | Frontier Airlines | Up to 1 stop each way | [Axel-exclusive $258.00](https://helloaxel.com/en/f/start/from/oak/to/ord/depart/december-18-2026/return/december-21-2026/adults/1/cabin/economy) |
| Dec 18, 2026 – Dec 21, 2026 · 3 nights · [Compare return dates departing Dec 18, 2026](https://helloaxel.com/en/flights/choose/oak-ord/dec-18) | Alaska Airlines | Up to 1 stop each way | [Axel-exclusive $420.00](https://helloaxel.com/en/f/start/from/oak/to/ord/depart/december-18-2026/return/december-21-2026/adults/1/cabin/economy) |
| Dec 19, 2026 – Dec 26, 2026 · 7 nights · [Compare return dates departing Dec 19, 2026](https://helloaxel.com/en/flights/choose/oak-ord/dec-19) | Frontier Airlines | Up to 1 stop each way | [Axel-exclusive $301.00](https://helloaxel.com/en/f/start/from/oak/to/ord/depart/december-19-2026/return/december-26-2026/adults/1/cabin/economy) |
| Dec 19, 2026 – Dec 26, 2026 · 7 nights · [Compare return dates departing Dec 19, 2026](https://helloaxel.com/en/flights/choose/oak-ord/dec-19) | Alaska Airlines | Up to 1 stop each way | [Axel-exclusive $490.00](https://helloaxel.com/en/f/start/from/oak/to/ord/depart/december-19-2026/return/december-26-2026/adults/1/cabin/economy) |
| Dec 22, 2026 · One way · [Compare return dates departing Dec 22, 2026](https://helloaxel.com/en/flights/choose/oak-ord/dec-22) | Frontier Airlines | Up to 1 stop each way | [Axel-exclusive $161.00](https://helloaxel.com/en/f/start/from/oak/to/ord/depart/december-22-2026/trip/one-way/adults/1/cabin/economy) |
| Dec 22, 2026 · One way · [Compare return dates departing Dec 22, 2026](https://helloaxel.com/en/flights/choose/oak-ord/dec-22) | Alaska Airlines | Up to 1 stop each way | [Axel-exclusive $259.00](https://helloaxel.com/en/f/start/from/oak/to/ord/depart/december-22-2026/trip/one-way/adults/1/cabin/economy) |
| Dec 22, 2026 – Dec 27, 2026 · 5 nights · [Compare return dates departing Dec 22, 2026](https://helloaxel.com/en/flights/choose/oak-ord/dec-22) | Frontier Airlines | Up to 1 stop each way | [Axel-exclusive $301.00](https://helloaxel.com/en/f/start/from/oak/to/ord/depart/december-22-2026/return/december-27-2026/adults/1/cabin/economy) |
| Dec 22, 2026 – Dec 27, 2026 · 5 nights · [Compare return dates departing Dec 22, 2026](https://helloaxel.com/en/flights/choose/oak-ord/dec-22) | Alaska Airlines | Up to 1 stop each way | [Axel-exclusive $490.00](https://helloaxel.com/en/f/start/from/oak/to/ord/depart/december-22-2026/return/december-27-2026/adults/1/cabin/economy) |
| Dec 24, 2026 – Dec 27, 2026 · 3 nights · [Compare return dates departing Dec 24, 2026](https://helloaxel.com/en/flights/choose/oak-ord/dec-24) | Frontier Airlines | Up to 1 stop each way | [Axel-exclusive $301.00](https://helloaxel.com/en/f/start/from/oak/to/ord/depart/december-24-2026/return/december-27-2026/adults/1/cabin/economy) |
| Dec 24, 2026 – Dec 27, 2026 · 3 nights · [Compare return dates departing Dec 24, 2026](https://helloaxel.com/en/flights/choose/oak-ord/dec-24) | Alaska Airlines | Up to 1 stop each way | [Axel-exclusive $490.00](https://helloaxel.com/en/f/start/from/oak/to/ord/depart/december-24-2026/return/december-27-2026/adults/1/cabin/economy) |
| Dec 25, 2026 – Dec 28, 2026 · 3 nights · [Compare return dates departing Dec 25, 2026](https://helloaxel.com/en/flights/choose/oak-ord/dec-25) | Frontier Airlines | Up to 1 stop each way | [Axel-exclusive $301.00](https://helloaxel.com/en/f/start/from/oak/to/ord/depart/december-25-2026/return/december-28-2026/adults/1/cabin/economy) |
| Dec 25, 2026 – Dec 28, 2026 · 3 nights · [Compare return dates departing Dec 25, 2026](https://helloaxel.com/en/flights/choose/oak-ord/dec-25) | Alaska Airlines | Up to 1 stop each way | [Axel-exclusive $490.00](https://helloaxel.com/en/f/start/from/oak/to/ord/depart/december-25-2026/return/december-28-2026/adults/1/cabin/economy) |
| Dec 26, 2026 – Jan 2, 2027 · 7 nights · [Compare return dates departing Dec 26, 2026](https://helloaxel.com/en/flights/choose/oak-ord/dec-26) | Frontier Airlines | Up to 1 stop each way | [Axel-exclusive $293.48](https://helloaxel.com/en/f/start/from/oak/to/ord/depart/december-26-2026/return/january-2-2027/adults/1/cabin/economy) |
| Dec 26, 2026 – Jan 2, 2027 · 7 nights · [Compare return dates departing Dec 26, 2026](https://helloaxel.com/en/flights/choose/oak-ord/dec-26) | Alaska Airlines | Up to 1 stop each way | [Axel-exclusive $477.75](https://helloaxel.com/en/f/start/from/oak/to/ord/depart/december-26-2026/return/january-2-2027/adults/1/cabin/economy) |
| Dec 29, 2026 · One way · [Compare return dates departing Dec 29, 2026](https://helloaxel.com/en/flights/choose/oak-ord/dec-29) | Frontier Airlines | Up to 1 stop each way | [Axel-exclusive $161.00](https://helloaxel.com/en/f/start/from/oak/to/ord/depart/december-29-2026/trip/one-way/adults/1/cabin/economy) |
| Dec 29, 2026 · One way · [Compare return dates departing Dec 29, 2026](https://helloaxel.com/en/flights/choose/oak-ord/dec-29) | Alaska Airlines | Up to 1 stop each way | [Axel-exclusive $259.00](https://helloaxel.com/en/f/start/from/oak/to/ord/depart/december-29-2026/trip/one-way/adults/1/cabin/economy) |
| Dec 30, 2026 – Jan 2, 2027 · 3 nights · [Compare return dates departing Dec 30, 2026](https://helloaxel.com/en/flights/choose/oak-ord/dec-30) | Frontier Airlines | Up to 1 stop each way | [Axel-exclusive $293.48](https://helloaxel.com/en/f/start/from/oak/to/ord/depart/december-30-2026/return/january-2-2027/adults/1/cabin/economy) |
| Dec 30, 2026 – Jan 2, 2027 · 3 nights · [Compare return dates departing Dec 30, 2026](https://helloaxel.com/en/flights/choose/oak-ord/dec-30) | Alaska Airlines | Up to 1 stop each way | [Axel-exclusive $477.75](https://helloaxel.com/en/f/start/from/oak/to/ord/depart/december-30-2026/return/january-2-2027/adults/1/cabin/economy) |
| Dec 31, 2026 – Jan 3, 2027 · 3 nights · [Compare return dates departing Dec 31, 2026](https://helloaxel.com/en/flights/choose/oak-ord/dec-31) | Frontier Airlines | Up to 1 stop each way | [Axel-exclusive $293.48](https://helloaxel.com/en/f/start/from/oak/to/ord/depart/december-31-2026/return/january-3-2027/adults/1/cabin/economy) |
| Dec 31, 2026 – Jan 3, 2027 · 3 nights · [Compare return dates departing Dec 31, 2026](https://helloaxel.com/en/flights/choose/oak-ord/dec-31) | Alaska Airlines | Up to 1 stop each way | [Axel-exclusive $477.75](https://helloaxel.com/en/f/start/from/oak/to/ord/depart/december-31-2026/return/january-3-2027/adults/1/cabin/economy) |

### Oakland (OAK) to Chicago (ORD): January 2027

| Travel dates | Airline | Stops | Total price |
| --- | --- | --- | ---: |
| Jan 1, 2027 – Jan 4, 2027 · 3 nights · [Compare return dates departing Jan 1, 2027](https://helloaxel.com/en/flights/choose/oak-ord/jan-1) | Frontier Airlines | Up to 1 stop each way | [Axel-exclusive $245.11](https://helloaxel.com/en/f/start/from/oak/to/ord/depart/january-1-2027/return/january-4-2027/adults/1/cabin/economy) |
| Jan 1, 2027 – Jan 4, 2027 · 3 nights · [Compare return dates departing Jan 1, 2027](https://helloaxel.com/en/flights/choose/oak-ord/jan-1) | Alaska Airlines | Up to 1 stop each way | [Axel-exclusive $399.00](https://helloaxel.com/en/f/start/from/oak/to/ord/depart/january-1-2027/return/january-4-2027/adults/1/cabin/economy) |
| Jan 2, 2027 – Jan 9, 2027 · 7 nights · [Compare return dates departing Jan 2, 2027](https://helloaxel.com/en/flights/choose/oak-ord/jan-2) | Frontier Airlines | Up to 1 stop each way | [Axel-exclusive $245.11](https://helloaxel.com/en/f/start/from/oak/to/ord/depart/january-2-2027/return/january-9-2027/adults/1/cabin/economy) |
| Jan 2, 2027 – Jan 9, 2027 · 7 nights · [Compare return dates departing Jan 2, 2027](https://helloaxel.com/en/flights/choose/oak-ord/jan-2) | Alaska Airlines | Up to 1 stop each way | [Axel-exclusive $399.00](https://helloaxel.com/en/f/start/from/oak/to/ord/depart/january-2-2027/return/january-9-2027/adults/1/cabin/economy) |
| Jan 5, 2027 · One way · [Compare return dates departing Jan 5, 2027](https://helloaxel.com/en/flights/choose/oak-ord/jan-5) | Frontier Airlines | Up to 1 stop each way | [Axel-exclusive $109.25](https://helloaxel.com/en/f/start/from/oak/to/ord/depart/january-5-2027/trip/one-way/adults/1/cabin/economy) |
| Jan 5, 2027 · One way · [Compare return dates departing Jan 5, 2027](https://helloaxel.com/en/flights/choose/oak-ord/jan-5) | Alaska Airlines | Up to 1 stop each way | [Axel-exclusive $175.75](https://helloaxel.com/en/f/start/from/oak/to/ord/depart/january-5-2027/trip/one-way/adults/1/cabin/economy) |
| Jan 7, 2027 – Jan 10, 2027 · 3 nights · [Compare return dates departing Jan 7, 2027](https://helloaxel.com/en/flights/choose/oak-ord/jan-7) | Frontier Airlines | Up to 1 stop each way | [Axel-exclusive $204.26](https://helloaxel.com/en/f/start/from/oak/to/ord/depart/january-7-2027/return/january-10-2027/adults/1/cabin/economy) |
| Jan 7, 2027 – Jan 10, 2027 · 3 nights · [Compare return dates departing Jan 7, 2027](https://helloaxel.com/en/flights/choose/oak-ord/jan-7) | Alaska Airlines | Up to 1 stop each way | [Axel-exclusive $332.50](https://helloaxel.com/en/f/start/from/oak/to/ord/depart/january-7-2027/return/january-10-2027/adults/1/cabin/economy) |
| Jan 8, 2027 – Jan 11, 2027 · 3 nights · [Compare return dates departing Jan 8, 2027](https://helloaxel.com/en/flights/choose/oak-ord/jan-8) | Frontier Airlines | Up to 1 stop each way | [Axel-exclusive $204.26](https://helloaxel.com/en/f/start/from/oak/to/ord/depart/january-8-2027/return/january-11-2027/adults/1/cabin/economy) |
| Jan 8, 2027 – Jan 11, 2027 · 3 nights · [Compare return dates departing Jan 8, 2027](https://helloaxel.com/en/flights/choose/oak-ord/jan-8) | Alaska Airlines | Up to 1 stop each way | [Axel-exclusive $332.50](https://helloaxel.com/en/f/start/from/oak/to/ord/depart/january-8-2027/return/january-11-2027/adults/1/cabin/economy) |
| Jan 9, 2027 – Jan 16, 2027 · 7 nights · [Compare return dates departing Jan 9, 2027](https://helloaxel.com/en/flights/choose/oak-ord/jan-9) | Frontier Airlines | Up to 1 stop each way | [Axel-exclusive $204.26](https://helloaxel.com/en/f/start/from/oak/to/ord/depart/january-9-2027/return/january-16-2027/adults/1/cabin/economy) |
| Jan 9, 2027 – Jan 16, 2027 · 7 nights · [Compare return dates departing Jan 9, 2027](https://helloaxel.com/en/flights/choose/oak-ord/jan-9) | Alaska Airlines | Up to 1 stop each way | [Axel-exclusive $332.50](https://helloaxel.com/en/f/start/from/oak/to/ord/depart/january-9-2027/return/january-16-2027/adults/1/cabin/economy) |
| Jan 12, 2027 · One way · [Compare return dates departing Jan 12, 2027](https://helloaxel.com/en/flights/choose/oak-ord/jan-12) | Frontier Airlines | Up to 1 stop each way | [Axel-exclusive $109.25](https://helloaxel.com/en/f/start/from/oak/to/ord/depart/january-12-2027/trip/one-way/adults/1/cabin/economy) |
| Jan 12, 2027 · One way · [Compare return dates departing Jan 12, 2027](https://helloaxel.com/en/flights/choose/oak-ord/jan-12) | Alaska Airlines | Up to 1 stop each way | [Axel-exclusive $175.75](https://helloaxel.com/en/f/start/from/oak/to/ord/depart/january-12-2027/trip/one-way/adults/1/cabin/economy) |
| Jan 14, 2027 – Jan 17, 2027 · 3 nights · [Compare return dates departing Jan 14, 2027](https://helloaxel.com/en/flights/choose/oak-ord/jan-14) | Frontier Airlines | Up to 1 stop each way | [Axel-exclusive $204.26](https://helloaxel.com/en/f/start/from/oak/to/ord/depart/january-14-2027/return/january-17-2027/adults/1/cabin/economy) |
| Jan 14, 2027 – Jan 17, 2027 · 3 nights · [Compare return dates departing Jan 14, 2027](https://helloaxel.com/en/flights/choose/oak-ord/jan-14) | Alaska Airlines | Up to 1 stop each way | [Axel-exclusive $332.50](https://helloaxel.com/en/f/start/from/oak/to/ord/depart/january-14-2027/return/january-17-2027/adults/1/cabin/economy) |
| Jan 15, 2027 – Jan 18, 2027 · 3 nights · [Compare return dates departing Jan 15, 2027](https://helloaxel.com/en/flights/choose/oak-ord/jan-15) | Frontier Airlines | Up to 1 stop each way | [Axel-exclusive $204.26](https://helloaxel.com/en/f/start/from/oak/to/ord/depart/january-15-2027/return/january-18-2027/adults/1/cabin/economy) |
| Jan 15, 2027 – Jan 18, 2027 · 3 nights · [Compare return dates departing Jan 15, 2027](https://helloaxel.com/en/flights/choose/oak-ord/jan-15) | Alaska Airlines | Up to 1 stop each way | [Axel-exclusive $332.50](https://helloaxel.com/en/f/start/from/oak/to/ord/depart/january-15-2027/return/january-18-2027/adults/1/cabin/economy) |
| Jan 16, 2027 – Jan 23, 2027 · 7 nights · [Compare return dates departing Jan 16, 2027](https://helloaxel.com/en/flights/choose/oak-ord/jan-16) | Frontier Airlines | Up to 1 stop each way | [Axel-exclusive $204.26](https://helloaxel.com/en/f/start/from/oak/to/ord/depart/january-16-2027/return/january-23-2027/adults/1/cabin/economy) |
| Jan 16, 2027 – Jan 23, 2027 · 7 nights · [Compare return dates departing Jan 16, 2027](https://helloaxel.com/en/flights/choose/oak-ord/jan-16) | Alaska Airlines | Up to 1 stop each way | [Axel-exclusive $332.50](https://helloaxel.com/en/f/start/from/oak/to/ord/depart/january-16-2027/return/january-23-2027/adults/1/cabin/economy) |
| Jan 19, 2027 · One way · [Compare return dates departing Jan 19, 2027](https://helloaxel.com/en/flights/choose/oak-ord/jan-19) | Frontier Airlines | Up to 1 stop each way | [Axel-exclusive $109.25](https://helloaxel.com/en/f/start/from/oak/to/ord/depart/january-19-2027/trip/one-way/adults/1/cabin/economy) |
| Jan 19, 2027 · One way · [Compare return dates departing Jan 19, 2027](https://helloaxel.com/en/flights/choose/oak-ord/jan-19) | Alaska Airlines | Up to 1 stop each way | [Axel-exclusive $175.75](https://helloaxel.com/en/f/start/from/oak/to/ord/depart/january-19-2027/trip/one-way/adults/1/cabin/economy) |
| Jan 21, 2027 – Jan 24, 2027 · 3 nights · [Compare return dates departing Jan 21, 2027](https://helloaxel.com/en/flights/choose/oak-ord/jan-21) | Frontier Airlines | Up to 1 stop each way | [Axel-exclusive $204.26](https://helloaxel.com/en/f/start/from/oak/to/ord/depart/january-21-2027/return/january-24-2027/adults/1/cabin/economy) |
| Jan 21, 2027 – Jan 24, 2027 · 3 nights · [Compare return dates departing Jan 21, 2027](https://helloaxel.com/en/flights/choose/oak-ord/jan-21) | Alaska Airlines | Up to 1 stop each way | [Axel-exclusive $332.50](https://helloaxel.com/en/f/start/from/oak/to/ord/depart/january-21-2027/return/january-24-2027/adults/1/cabin/economy) |
| Jan 22, 2027 – Jan 25, 2027 · 3 nights · [Compare return dates departing Jan 22, 2027](https://helloaxel.com/en/flights/choose/oak-ord/jan-22) | Frontier Airlines | Up to 1 stop each way | [Axel-exclusive $204.26](https://helloaxel.com/en/f/start/from/oak/to/ord/depart/january-22-2027/return/january-25-2027/adults/1/cabin/economy) |
| Jan 22, 2027 – Jan 25, 2027 · 3 nights · [Compare return dates departing Jan 22, 2027](https://helloaxel.com/en/flights/choose/oak-ord/jan-22) | Alaska Airlines | Up to 1 stop each way | [Axel-exclusive $332.50](https://helloaxel.com/en/f/start/from/oak/to/ord/depart/january-22-2027/return/january-25-2027/adults/1/cabin/economy) |
| Jan 23, 2027 – Jan 30, 2027 · 7 nights · [Compare return dates departing Jan 23, 2027](https://helloaxel.com/en/flights/choose/oak-ord/jan-23) | Frontier Airlines | Up to 1 stop each way | [Axel-exclusive $204.26](https://helloaxel.com/en/f/start/from/oak/to/ord/depart/january-23-2027/return/january-30-2027/adults/1/cabin/economy) |
| Jan 23, 2027 – Jan 30, 2027 · 7 nights · [Compare return dates departing Jan 23, 2027](https://helloaxel.com/en/flights/choose/oak-ord/jan-23) | Alaska Airlines | Up to 1 stop each way | [Axel-exclusive $332.50](https://helloaxel.com/en/f/start/from/oak/to/ord/depart/january-23-2027/return/january-30-2027/adults/1/cabin/economy) |
| Jan 26, 2027 · One way · [Compare return dates departing Jan 26, 2027](https://helloaxel.com/en/flights/choose/oak-ord/jan-26) | Frontier Airlines | Up to 1 stop each way | [Axel-exclusive $109.25](https://helloaxel.com/en/f/start/from/oak/to/ord/depart/january-26-2027/trip/one-way/adults/1/cabin/economy) |
| Jan 26, 2027 · One way · [Compare return dates departing Jan 26, 2027](https://helloaxel.com/en/flights/choose/oak-ord/jan-26) | Alaska Airlines | Up to 1 stop each way | [Axel-exclusive $175.75](https://helloaxel.com/en/f/start/from/oak/to/ord/depart/january-26-2027/trip/one-way/adults/1/cabin/economy) |
| Jan 28, 2027 – Jan 31, 2027 · 3 nights · [Compare return dates departing Jan 28, 2027](https://helloaxel.com/en/flights/choose/oak-ord/jan-28) | Frontier Airlines | Up to 1 stop each way | [Axel-exclusive $204.26](https://helloaxel.com/en/f/start/from/oak/to/ord/depart/january-28-2027/return/january-31-2027/adults/1/cabin/economy) |
| Jan 28, 2027 – Jan 31, 2027 · 3 nights · [Compare return dates departing Jan 28, 2027](https://helloaxel.com/en/flights/choose/oak-ord/jan-28) | Alaska Airlines | Up to 1 stop each way | [Axel-exclusive $332.50](https://helloaxel.com/en/f/start/from/oak/to/ord/depart/january-28-2027/return/january-31-2027/adults/1/cabin/economy) |
| Jan 29, 2027 – Feb 1, 2027 · 3 nights · [Compare return dates departing Jan 29, 2027](https://helloaxel.com/en/flights/choose/oak-ord/jan-29) | Frontier Airlines | Up to 1 stop each way | [Axel-exclusive $204.26](https://helloaxel.com/en/f/start/from/oak/to/ord/depart/january-29-2027/return/february-1-2027/adults/1/cabin/economy) |
| Jan 29, 2027 – Feb 1, 2027 · 3 nights · [Compare return dates departing Jan 29, 2027](https://helloaxel.com/en/flights/choose/oak-ord/jan-29) | Alaska Airlines | Up to 1 stop each way | [Axel-exclusive $332.50](https://helloaxel.com/en/f/start/from/oak/to/ord/depart/january-29-2027/return/february-1-2027/adults/1/cabin/economy) |
| Jan 30, 2027 – Feb 6, 2027 · 7 nights · [Compare return dates departing Jan 30, 2027](https://helloaxel.com/en/flights/choose/oak-ord/jan-30) | Frontier Airlines | Up to 1 stop each way | [Axel-exclusive $204.26](https://helloaxel.com/en/f/start/from/oak/to/ord/depart/january-30-2027/return/february-6-2027/adults/1/cabin/economy) |
| Jan 30, 2027 – Feb 6, 2027 · 7 nights · [Compare return dates departing Jan 30, 2027](https://helloaxel.com/en/flights/choose/oak-ord/jan-30) | Alaska Airlines | Up to 1 stop each way | [Axel-exclusive $332.50](https://helloaxel.com/en/f/start/from/oak/to/ord/depart/january-30-2027/return/february-6-2027/adults/1/cabin/economy) |

### Oakland (OAK) to Chicago (ORD): February 2027

| Travel dates | Airline | Stops | Total price |
| --- | --- | --- | ---: |
| Feb 2, 2027 · One way · [Compare return dates departing Feb 2, 2027](https://helloaxel.com/en/flights/choose/oak-ord/feb-2) | Frontier Airlines | Up to 1 stop each way | [Axel-exclusive $109.25](https://helloaxel.com/en/f/start/from/oak/to/ord/depart/february-2-2027/trip/one-way/adults/1/cabin/economy) |
| Feb 2, 2027 · One way · [Compare return dates departing Feb 2, 2027](https://helloaxel.com/en/flights/choose/oak-ord/feb-2) | Alaska Airlines | Up to 1 stop each way | [Axel-exclusive $175.75](https://helloaxel.com/en/f/start/from/oak/to/ord/depart/february-2-2027/trip/one-way/adults/1/cabin/economy) |
| Feb 4, 2027 – Feb 7, 2027 · 3 nights · [Compare return dates departing Feb 4, 2027](https://helloaxel.com/en/flights/choose/oak-ord/feb-4) | Frontier Airlines | Up to 1 stop each way | [Axel-exclusive $204.26](https://helloaxel.com/en/f/start/from/oak/to/ord/depart/february-4-2027/return/february-7-2027/adults/1/cabin/economy) |
| Feb 4, 2027 – Feb 7, 2027 · 3 nights · [Compare return dates departing Feb 4, 2027](https://helloaxel.com/en/flights/choose/oak-ord/feb-4) | Alaska Airlines | Up to 1 stop each way | [Axel-exclusive $332.50](https://helloaxel.com/en/f/start/from/oak/to/ord/depart/february-4-2027/return/february-7-2027/adults/1/cabin/economy) |
| Feb 5, 2027 – Feb 8, 2027 · 3 nights · [Compare return dates departing Feb 5, 2027](https://helloaxel.com/en/flights/choose/oak-ord/feb-5) | Frontier Airlines | Up to 1 stop each way | [Axel-exclusive $204.26](https://helloaxel.com/en/f/start/from/oak/to/ord/depart/february-5-2027/return/february-8-2027/adults/1/cabin/economy) |
| Feb 5, 2027 – Feb 8, 2027 · 3 nights · [Compare return dates departing Feb 5, 2027](https://helloaxel.com/en/flights/choose/oak-ord/feb-5) | Alaska Airlines | Up to 1 stop each way | [Axel-exclusive $332.50](https://helloaxel.com/en/f/start/from/oak/to/ord/depart/february-5-2027/return/february-8-2027/adults/1/cabin/economy) |
| Feb 6, 2027 – Feb 13, 2027 · 7 nights · [Compare return dates departing Feb 6, 2027](https://helloaxel.com/en/flights/choose/oak-ord/feb-6) | Frontier Airlines | Up to 1 stop each way | [Axel-exclusive $219.31](https://helloaxel.com/en/f/start/from/oak/to/ord/depart/february-6-2027/return/february-13-2027/adults/1/cabin/economy) |
| Feb 6, 2027 – Feb 13, 2027 · 7 nights · [Compare return dates departing Feb 6, 2027](https://helloaxel.com/en/flights/choose/oak-ord/feb-6) | Alaska Airlines | Up to 1 stop each way | [Axel-exclusive $357.00](https://helloaxel.com/en/f/start/from/oak/to/ord/depart/february-6-2027/return/february-13-2027/adults/1/cabin/economy) |
| Feb 12, 2027 – Feb 15, 2027 · 3 nights · [Compare return dates departing Feb 12, 2027](https://helloaxel.com/en/flights/choose/oak-ord/feb-12) | Frontier Airlines | Up to 1 stop each way | [Axel-exclusive $234.36](https://helloaxel.com/en/f/start/from/oak/to/ord/depart/february-12-2027/return/february-15-2027/adults/1/cabin/economy) |
| Feb 12, 2027 – Feb 15, 2027 · 3 nights · [Compare return dates departing Feb 12, 2027](https://helloaxel.com/en/flights/choose/oak-ord/feb-12) | Alaska Airlines | Up to 1 stop each way | [Axel-exclusive $381.50](https://helloaxel.com/en/f/start/from/oak/to/ord/depart/february-12-2027/return/february-15-2027/adults/1/cabin/economy) |
| Feb 19, 2027 – Feb 22, 2027 · 3 nights · [Compare return dates departing Feb 19, 2027](https://helloaxel.com/en/flights/choose/oak-ord/feb-19) | Frontier Airlines | Up to 1 stop each way | [Axel-exclusive $204.26](https://helloaxel.com/en/f/start/from/oak/to/ord/depart/february-19-2027/return/february-22-2027/adults/1/cabin/economy) |
| Feb 19, 2027 – Feb 22, 2027 · 3 nights · [Compare return dates departing Feb 19, 2027](https://helloaxel.com/en/flights/choose/oak-ord/feb-19) | Alaska Airlines | Up to 1 stop each way | [Axel-exclusive $332.50](https://helloaxel.com/en/f/start/from/oak/to/ord/depart/february-19-2027/return/february-22-2027/adults/1/cabin/economy) |
| Feb 20, 2027 – Feb 27, 2027 · 7 nights · [Compare return dates departing Feb 20, 2027](https://helloaxel.com/en/flights/choose/oak-ord/feb-20) | Frontier Airlines | Up to 1 stop each way | [Axel-exclusive $204.26](https://helloaxel.com/en/f/start/from/oak/to/ord/depart/february-20-2027/return/february-27-2027/adults/1/cabin/economy) |
| Feb 20, 2027 – Feb 27, 2027 · 7 nights · [Compare return dates departing Feb 20, 2027](https://helloaxel.com/en/flights/choose/oak-ord/feb-20) | Alaska Airlines | Up to 1 stop each way | [Axel-exclusive $332.50](https://helloaxel.com/en/f/start/from/oak/to/ord/depart/february-20-2027/return/february-27-2027/adults/1/cabin/economy) |

### Oakland (OAK) to Chicago (ORD): March 2027

| Travel dates | Airline | Stops | Total price |
| --- | --- | --- | ---: |
| Mar 19, 2027 – Mar 22, 2027 · 3 nights · [Compare return dates departing Mar 19, 2027](https://helloaxel.com/en/flights/choose/oak-ord/mar-19) | Frontier Airlines | Up to 1 stop each way | [Axel-exclusive $248.33](https://helloaxel.com/en/f/start/from/oak/to/ord/depart/march-19-2027/return/march-22-2027/adults/1/cabin/economy) |
| Mar 19, 2027 – Mar 22, 2027 · 3 nights · [Compare return dates departing Mar 19, 2027](https://helloaxel.com/en/flights/choose/oak-ord/mar-19) | Alaska Airlines | Up to 1 stop each way | [Axel-exclusive $404.25](https://helloaxel.com/en/f/start/from/oak/to/ord/depart/march-19-2027/return/march-22-2027/adults/1/cabin/economy) |
| Mar 20, 2027 – Mar 27, 2027 · 7 nights · [Compare return dates departing Mar 20, 2027](https://helloaxel.com/en/flights/choose/oak-ord/mar-20) | Frontier Airlines | Up to 1 stop each way | [Axel-exclusive $270.90](https://helloaxel.com/en/f/start/from/oak/to/ord/depart/march-20-2027/return/march-27-2027/adults/1/cabin/economy) |
| Mar 20, 2027 – Mar 27, 2027 · 7 nights · [Compare return dates departing Mar 20, 2027](https://helloaxel.com/en/flights/choose/oak-ord/mar-20) | Alaska Airlines | Up to 1 stop each way | [Axel-exclusive $441.00](https://helloaxel.com/en/f/start/from/oak/to/ord/depart/march-20-2027/return/march-27-2027/adults/1/cabin/economy) |
| Mar 25, 2027 – Mar 29, 2027 · 4 nights · [Compare return dates departing Mar 25, 2027](https://helloaxel.com/en/flights/choose/oak-ord/mar-25) | Frontier Airlines | Up to 1 stop each way | [Axel-exclusive $308.70](https://helloaxel.com/en/f/start/from/oak/to/ord/depart/march-25-2027/return/march-29-2027/adults/1/cabin/economy) |
| Mar 25, 2027 – Mar 29, 2027 · 4 nights · [Compare return dates departing Mar 25, 2027](https://helloaxel.com/en/flights/choose/oak-ord/mar-25) | Alaska Airlines | Up to 1 stop each way | [Axel-exclusive $485.10](https://helloaxel.com/en/f/start/from/oak/to/ord/depart/march-25-2027/return/march-29-2027/adults/1/cabin/economy) |

### Oakland (OAK) to Chicago (ORD): April 2027

| Travel dates | Airline | Stops | Total price |
| --- | --- | --- | ---: |
| Apr 16, 2027 – Apr 19, 2027 · 3 nights · [Compare return dates departing Apr 16, 2027](https://helloaxel.com/en/flights/choose/oak-ord/apr-16) | Frontier Airlines | Up to 1 stop each way | [Axel-exclusive $275.00](https://helloaxel.com/en/f/start/from/oak/to/ord/depart/april-16-2027/return/april-19-2027/adults/1/cabin/economy) |
| Apr 16, 2027 – Apr 19, 2027 · 3 nights · [Compare return dates departing Apr 16, 2027](https://helloaxel.com/en/flights/choose/oak-ord/apr-16) | Alaska Airlines | Up to 1 stop each way | [Axel-exclusive $420.00](https://helloaxel.com/en/f/start/from/oak/to/ord/depart/april-16-2027/return/april-19-2027/adults/1/cabin/economy) |
| Apr 17, 2027 – Apr 24, 2027 · 7 nights · [Compare return dates departing Apr 17, 2027](https://helloaxel.com/en/flights/choose/oak-ord/apr-17) | Frontier Airlines | Up to 1 stop each way | [Axel-exclusive $275.00](https://helloaxel.com/en/f/start/from/oak/to/ord/depart/april-17-2027/return/april-24-2027/adults/1/cabin/economy) |
| Apr 17, 2027 – Apr 24, 2027 · 7 nights · [Compare return dates departing Apr 17, 2027](https://helloaxel.com/en/flights/choose/oak-ord/apr-17) | Alaska Airlines | Up to 1 stop each way | [Axel-exclusive $420.00](https://helloaxel.com/en/f/start/from/oak/to/ord/depart/april-17-2027/return/april-24-2027/adults/1/cabin/economy) |

### Oakland (OAK) to Chicago (ORD): May 2027

| Travel dates | Airline | Stops | Total price |
| --- | --- | --- | ---: |
| May 14, 2027 – May 17, 2027 · 3 nights · [Compare return dates departing May 14, 2027](https://helloaxel.com/en/flights/choose/oak-ord/may-14) | Frontier Airlines | Up to 1 stop each way | [Axel-exclusive $275.00](https://helloaxel.com/en/f/start/from/oak/to/ord/depart/may-14-2027/return/may-17-2027/adults/1/cabin/economy) |
| May 14, 2027 – May 17, 2027 · 3 nights · [Compare return dates departing May 14, 2027](https://helloaxel.com/en/flights/choose/oak-ord/may-14) | Alaska Airlines | Up to 1 stop each way | [Axel-exclusive $420.00](https://helloaxel.com/en/f/start/from/oak/to/ord/depart/may-14-2027/return/may-17-2027/adults/1/cabin/economy) |
| May 15, 2027 – May 22, 2027 · 7 nights · [Compare return dates departing May 15, 2027](https://helloaxel.com/en/flights/choose/oak-ord/may-15) | Frontier Airlines | Up to 1 stop each way | [Axel-exclusive $275.00](https://helloaxel.com/en/f/start/from/oak/to/ord/depart/may-15-2027/return/may-22-2027/adults/1/cabin/economy) |
| May 15, 2027 – May 22, 2027 · 7 nights · [Compare return dates departing May 15, 2027](https://helloaxel.com/en/flights/choose/oak-ord/may-15) | Alaska Airlines | Up to 1 stop each way | [Axel-exclusive $420.00](https://helloaxel.com/en/f/start/from/oak/to/ord/depart/may-15-2027/return/may-22-2027/adults/1/cabin/economy) |
| May 28, 2027 – May 31, 2027 · 3 nights · [Compare return dates departing May 28, 2027](https://helloaxel.com/en/flights/choose/oak-ord/may-28) | Frontier Airlines | Up to 1 stop each way | [Axel-exclusive $330.00](https://helloaxel.com/en/f/start/from/oak/to/ord/depart/may-28-2027/return/may-31-2027/adults/1/cabin/economy) |
| May 28, 2027 – May 31, 2027 · 3 nights · [Compare return dates departing May 28, 2027](https://helloaxel.com/en/flights/choose/oak-ord/may-28) | Alaska Airlines | Up to 1 stop each way | [Axel-exclusive $504.00](https://helloaxel.com/en/f/start/from/oak/to/ord/depart/may-28-2027/return/may-31-2027/adults/1/cabin/economy) |

### Oakland (OAK) to Chicago (ORD): June 2027

| Travel dates | Airline | Stops | Total price |
| --- | --- | --- | ---: |
| Jun 11, 2027 – Jun 14, 2027 · 3 nights · [Compare return dates departing Jun 11, 2027](https://helloaxel.com/en/flights/choose/oak-ord/jun-11) | Frontier Airlines | Up to 1 stop each way | [Axel-exclusive $275.00](https://helloaxel.com/en/f/start/from/oak/to/ord/depart/june-11-2027/return/june-14-2027/adults/1/cabin/economy) |
| Jun 11, 2027 – Jun 14, 2027 · 3 nights · [Compare return dates departing Jun 11, 2027](https://helloaxel.com/en/flights/choose/oak-ord/jun-11) | Alaska Airlines | Up to 1 stop each way | [Axel-exclusive $420.00](https://helloaxel.com/en/f/start/from/oak/to/ord/depart/june-11-2027/return/june-14-2027/adults/1/cabin/economy) |
| Jun 12, 2027 – Jun 19, 2027 · 7 nights · [Compare return dates departing Jun 12, 2027](https://helloaxel.com/en/flights/choose/oak-ord/jun-12) | Frontier Airlines | Up to 1 stop each way | [Axel-exclusive $275.00](https://helloaxel.com/en/f/start/from/oak/to/ord/depart/june-12-2027/return/june-19-2027/adults/1/cabin/economy) |
| Jun 12, 2027 – Jun 19, 2027 · 7 nights · [Compare return dates departing Jun 12, 2027](https://helloaxel.com/en/flights/choose/oak-ord/jun-12) | Alaska Airlines | Up to 1 stop each way | [Axel-exclusive $420.00](https://helloaxel.com/en/f/start/from/oak/to/ord/depart/june-12-2027/return/june-19-2027/adults/1/cabin/economy) |

### Oakland (OAK) to Chicago (ORD): July 2027

| Travel dates | Airline | Stops | Total price |
| --- | --- | --- | ---: |
| Jul 2, 2027 – Jul 6, 2027 · 4 nights · [Compare return dates departing Jul 2, 2027](https://helloaxel.com/en/flights/choose/oak-ord/jul-2) | Frontier Airlines | Up to 1 stop each way | [Axel-exclusive $346.50](https://helloaxel.com/en/f/start/from/oak/to/ord/depart/july-2-2027/return/july-6-2027/adults/1/cabin/economy) |
| Jul 2, 2027 – Jul 6, 2027 · 4 nights · [Compare return dates departing Jul 2, 2027](https://helloaxel.com/en/flights/choose/oak-ord/jul-2) | Delta Air Lines / Frontier Airlines | Up to 1 stop each way | [Axel-exclusive $463.05](https://helloaxel.com/en/f/start/from/oak/to/ord/depart/july-2-2027/return/july-6-2027/adults/1/cabin/economy) |
| Jul 9, 2027 – Jul 12, 2027 · 3 nights · [Compare return dates departing Jul 9, 2027](https://helloaxel.com/en/flights/choose/oak-ord/jul-9) | Frontier Airlines | Up to 1 stop each way | [Axel-exclusive $288.76](https://helloaxel.com/en/f/start/from/oak/to/ord/depart/july-9-2027/return/july-12-2027/adults/1/cabin/economy) |
| Jul 9, 2027 – Jul 12, 2027 · 3 nights · [Compare return dates departing Jul 9, 2027](https://helloaxel.com/en/flights/choose/oak-ord/jul-9) | Alaska Airlines | Up to 1 stop each way | [Axel-exclusive $441.00](https://helloaxel.com/en/f/start/from/oak/to/ord/depart/july-9-2027/return/july-12-2027/adults/1/cabin/economy) |
| Jul 10, 2027 – Jul 17, 2027 · 7 nights · [Compare return dates departing Jul 10, 2027](https://helloaxel.com/en/flights/choose/oak-ord/jul-10) | Frontier Airlines | Up to 1 stop each way | [Axel-exclusive $288.76](https://helloaxel.com/en/f/start/from/oak/to/ord/depart/july-10-2027/return/july-17-2027/adults/1/cabin/economy) |
| Jul 10, 2027 – Jul 17, 2027 · 7 nights · [Compare return dates departing Jul 10, 2027](https://helloaxel.com/en/flights/choose/oak-ord/jul-10) | Alaska Airlines | Up to 1 stop each way | [Axel-exclusive $441.00](https://helloaxel.com/en/f/start/from/oak/to/ord/depart/july-10-2027/return/july-17-2027/adults/1/cabin/economy) |

### Oakland (OAK) to Chicago (ORD): August 2027

| Travel dates | Airline | Stops | Total price |
| --- | --- | --- | ---: |
| Aug 6, 2027 – Aug 9, 2027 · 3 nights · [Compare return dates departing Aug 6, 2027](https://helloaxel.com/en/flights/choose/oak-ord/aug-6) | Frontier Airlines | Up to 1 stop each way | [Axel-exclusive $275.00](https://helloaxel.com/en/f/start/from/oak/to/ord/depart/august-6-2027/return/august-9-2027/adults/1/cabin/economy) |
| Aug 6, 2027 – Aug 9, 2027 · 3 nights · [Compare return dates departing Aug 6, 2027](https://helloaxel.com/en/flights/choose/oak-ord/aug-6) | Alaska Airlines | Up to 1 stop each way | [Axel-exclusive $420.00](https://helloaxel.com/en/f/start/from/oak/to/ord/depart/august-6-2027/return/august-9-2027/adults/1/cabin/economy) |
| Aug 7, 2027 – Aug 14, 2027 · 7 nights · [Compare return dates departing Aug 7, 2027](https://helloaxel.com/en/flights/choose/oak-ord/aug-7) | Frontier Airlines | Up to 1 stop each way | [Axel-exclusive $275.00](https://helloaxel.com/en/f/start/from/oak/to/ord/depart/august-7-2027/return/august-14-2027/adults/1/cabin/economy) |
| Aug 7, 2027 – Aug 14, 2027 · 7 nights · [Compare return dates departing Aug 7, 2027](https://helloaxel.com/en/flights/choose/oak-ord/aug-7) | Alaska Airlines | Up to 1 stop each way | [Axel-exclusive $420.00](https://helloaxel.com/en/f/start/from/oak/to/ord/depart/august-7-2027/return/august-14-2027/adults/1/cabin/economy) |

### Oakland (OAK) to Chicago (ORD): September 2027

| Travel dates | Airline | Stops | Total price |
| --- | --- | --- | ---: |
| Sep 3, 2027 – Sep 6, 2027 · 3 nights · [Compare return dates departing Sep 3, 2027](https://helloaxel.com/en/flights/choose/oak-ord/sep-3) | Frontier Airlines | Up to 1 stop each way | [Axel-exclusive $313.50](https://helloaxel.com/en/f/start/from/oak/to/ord/depart/september-3-2027/return/september-6-2027/adults/1/cabin/economy) |
| Sep 3, 2027 – Sep 6, 2027 · 3 nights · [Compare return dates departing Sep 3, 2027](https://helloaxel.com/en/flights/choose/oak-ord/sep-3) | Alaska Airlines | Up to 1 stop each way | [Axel-exclusive $478.80](https://helloaxel.com/en/f/start/from/oak/to/ord/depart/september-3-2027/return/september-6-2027/adults/1/cabin/economy) |
| Sep 4, 2027 – Sep 11, 2027 · 7 nights · [Compare return dates departing Sep 4, 2027](https://helloaxel.com/en/flights/choose/oak-ord/sep-4) | Frontier Airlines | Up to 1 stop each way | [Axel-exclusive $287.38](https://helloaxel.com/en/f/start/from/oak/to/ord/depart/september-4-2027/return/september-11-2027/adults/1/cabin/economy) |
| Sep 4, 2027 – Sep 11, 2027 · 7 nights · [Compare return dates departing Sep 4, 2027](https://helloaxel.com/en/flights/choose/oak-ord/sep-4) | Alaska Airlines | Up to 1 stop each way | [Axel-exclusive $438.90](https://helloaxel.com/en/f/start/from/oak/to/ord/depart/september-4-2027/return/september-11-2027/adults/1/cabin/economy) |
| Sep 24, 2027 – Sep 27, 2027 · 3 nights · [Compare return dates departing Sep 24, 2027](https://helloaxel.com/en/flights/choose/oak-ord/sep-24) | Frontier Airlines | Up to 1 stop each way | [Axel-exclusive $261.26](https://helloaxel.com/en/f/start/from/oak/to/ord/depart/september-24-2027/return/september-27-2027/adults/1/cabin/economy) |
| Sep 24, 2027 – Sep 27, 2027 · 3 nights · [Compare return dates departing Sep 24, 2027](https://helloaxel.com/en/flights/choose/oak-ord/sep-24) | Alaska Airlines | Up to 1 stop each way | [Axel-exclusive $399.00](https://helloaxel.com/en/f/start/from/oak/to/ord/depart/september-24-2027/return/september-27-2027/adults/1/cabin/economy) |
| Sep 25, 2027 – Oct 2, 2027 · 7 nights · [Compare return dates departing Sep 25, 2027](https://helloaxel.com/en/flights/choose/oak-ord/sep-25) | Frontier Airlines | Up to 1 stop each way | [Axel-exclusive $268.13](https://helloaxel.com/en/f/start/from/oak/to/ord/depart/september-25-2027/return/october-2-2027/adults/1/cabin/economy) |
| Sep 25, 2027 – Oct 2, 2027 · 7 nights · [Compare return dates departing Sep 25, 2027](https://helloaxel.com/en/flights/choose/oak-ord/sep-25) | Alaska Airlines | Up to 1 stop each way | [Axel-exclusive $409.50](https://helloaxel.com/en/f/start/from/oak/to/ord/depart/september-25-2027/return/october-2-2027/adults/1/cabin/economy) |

### Hotels in Chicago for these trips

**Hotels:** under a trip, hotels in Chicago for exactly those nights link to the hotel pages for 2 adults in 1 room. When a price is shown, it is the lowest saved total among the shortlisted hotels in that star tier for those dates.

- Hotels in Chicago for these nights (Nov 19–22, 2026 · 3 nights · 2 adults, 1 room): 3★ [The Chicago Hotel Collection River North, $512 total](https://helloaxel.com/en/hotels/chicago/the-chicago-hotel-collection-river-north-1389180/2026-11-19/2026-11-22/2-adults) · 4★ [Millennium Hotel Knickerbocker Chicago, $536 total](https://helloaxel.com/en/hotels/chicago/millennium-hotel-knickerbocker-chicago-1046970/2026-11-19/2026-11-22/2-adults) · 5★ [Sofitel Chicago Magnificent Mile, $864.50 total](https://helloaxel.com/en/hotels/chicago/sofitel-chicago-magnificent-mile-1279364/2026-11-19/2026-11-22/2-adults)
- Hotels in Chicago for these nights (Nov 20–23, 2026 · 3 nights · 2 adults, 1 room): 3★ [Congress Plaza Hotel, $487 total](https://helloaxel.com/en/hotels/chicago/congress-plaza-hotel-1239823/2026-11-20/2026-11-23/2-adults) · 4★ [The Midland Hotel, Chicago, A Tribute Portfolio Hotel, $479 total](https://helloaxel.com/en/hotels/chicago/the-midland-hotel-chicago-a-tribute-portfolio-hotel-1102199/2026-11-20/2026-11-23/2-adults) · 5★ [Sofitel Chicago Magnificent Mile, $760.50 total](https://helloaxel.com/en/hotels/chicago/sofitel-chicago-magnificent-mile-1279364/2026-11-20/2026-11-23/2-adults)
- Hotels in Chicago for these nights (Nov 21–28, 2026 · 7 nights · 2 adults, 1 room): 3★ [The Whitehall Hotel, BW Premier Collection, $904 total](https://helloaxel.com/en/hotels/chicago/the-whitehall-hotel-bw-premier-collection-1066968/2026-11-21/2026-11-28/2-adults) · 4★ [Crowne Plaza Chicago West Loop by IHG, $890 total](https://helloaxel.com/en/hotels/chicago/crowne-plaza-chicago-west-loop-by-ihg-1037469/2026-11-21/2026-11-28/2-adults) · 5★ [Sofitel Chicago Magnificent Mile, $1,588.50 total](https://helloaxel.com/en/hotels/chicago/sofitel-chicago-magnificent-mile-1279364/2026-11-21/2026-11-28/2-adults)
- Hotels in Chicago for these nights (Nov 24–29, 2026 · 5 nights · 2 adults, 1 room): 3★ [The Whitehall Hotel, BW Premier Collection, $655 total](https://helloaxel.com/en/hotels/chicago/the-whitehall-hotel-bw-premier-collection-1066968/2026-11-24/2026-11-29/2-adults) · 4★ [Crowne Plaza Chicago West Loop by IHG, $621 total](https://helloaxel.com/en/hotels/chicago/crowne-plaza-chicago-west-loop-by-ihg-1037469/2026-11-24/2026-11-29/2-adults) · 5★ [Sofitel Chicago Magnificent Mile, $1,212 total](https://helloaxel.com/en/hotels/chicago/sofitel-chicago-magnificent-mile-1279364/2026-11-24/2026-11-29/2-adults)
- Hotels in Chicago for these nights (Nov 26–29, 2026 · 3 nights · 2 adults, 1 room): 3★ [The Chicago Hotel Collection River North, $447 total](https://helloaxel.com/en/hotels/chicago/the-chicago-hotel-collection-river-north-1389180/2026-11-26/2026-11-29/2-adults) · 4★ [Crowne Plaza Chicago West Loop by IHG, $412 total](https://helloaxel.com/en/hotels/chicago/crowne-plaza-chicago-west-loop-by-ihg-1037469/2026-11-26/2026-11-29/2-adults) · 5★ [Sofitel Chicago Magnificent Mile, $799 total](https://helloaxel.com/en/hotels/chicago/sofitel-chicago-magnificent-mile-1279364/2026-11-26/2026-11-29/2-adults)
- Hotels in Chicago for these nights (Nov 27–30, 2026 · 3 nights · 2 adults, 1 room): 3★ [The Chicago Hotel Collection River North, $424 total](https://helloaxel.com/en/hotels/chicago/the-chicago-hotel-collection-river-north-1389180/2026-11-27/2026-11-30/2-adults) · 4★ [Crowne Plaza Chicago West Loop by IHG, $437 total](https://helloaxel.com/en/hotels/chicago/crowne-plaza-chicago-west-loop-by-ihg-1037469/2026-11-27/2026-11-30/2-adults) · 5★ [Sofitel Chicago Magnificent Mile, $909 total](https://helloaxel.com/en/hotels/chicago/sofitel-chicago-magnificent-mile-1279364/2026-11-27/2026-11-30/2-adults)
- Hotels in Chicago for these nights (Nov 28 – Dec 5, 2026 · 7 nights · 2 adults, 1 room): 3★ [The Willows Hotel, $871 total](https://helloaxel.com/en/hotels/chicago/the-willows-hotel-1255911/2026-11-28/2026-12-05/2-adults) · 4★ [The Chicago Hotel Collection Ambassador Gold Coast, $1,030 total](https://helloaxel.com/en/hotels/chicago/the-chicago-hotel-collection-ambassador-gold-coast-1066105/2026-11-28/2026-12-05/2-adults) · 5★ [Sofitel Chicago Magnificent Mile, $2,060 total](https://helloaxel.com/en/hotels/chicago/sofitel-chicago-magnificent-mile-1279364/2026-11-28/2026-12-05/2-adults)
- Hotels in Chicago for these nights (Dec 3–6, 2026 · 3 nights · 2 adults, 1 room): 3★ [Congress Plaza Hotel, $411 total](https://helloaxel.com/en/hotels/chicago/congress-plaza-hotel-1239823/2026-12-03/2026-12-06/2-adults) · 4★ [Warwick Allerton - Chicago, $391 total](https://helloaxel.com/en/hotels/chicago/warwick-allerton-chicago-1114033/2026-12-03/2026-12-06/2-adults) · 5★ [Sofitel Chicago Magnificent Mile, $840 total](https://helloaxel.com/en/hotels/chicago/sofitel-chicago-magnificent-mile-1279364/2026-12-03/2026-12-06/2-adults)
- Hotels in Chicago for these nights (Dec 4–7, 2026 · 3 nights · 2 adults, 1 room): 3★ [Congress Plaza Hotel, $390 total](https://helloaxel.com/en/hotels/chicago/congress-plaza-hotel-1239823/2026-12-04/2026-12-07/2-adults) · 4★ [Warwick Allerton - Chicago, $368 total](https://helloaxel.com/en/hotels/chicago/warwick-allerton-chicago-1114033/2026-12-04/2026-12-07/2-adults) · 5★ [Sofitel Chicago Magnificent Mile, $812 total](https://helloaxel.com/en/hotels/chicago/sofitel-chicago-magnificent-mile-1279364/2026-12-04/2026-12-07/2-adults)
- Hotels in Chicago for these nights (Dec 5–12, 2026 · 7 nights · 2 adults, 1 room): 3★ [The Whitehall Hotel, BW Premier Collection, $739 total](https://helloaxel.com/en/hotels/chicago/the-whitehall-hotel-bw-premier-collection-1066968/2026-12-05/2026-12-12/2-adults) · 4★ [Warwick Allerton - Chicago, $706 total](https://helloaxel.com/en/hotels/chicago/warwick-allerton-chicago-1114033/2026-12-05/2026-12-12/2-adults) · 5★ [Waldorf Astoria Chicago, $4,190 total](https://helloaxel.com/en/hotels/chicago/waldorf-astoria-chicago-1119995/2026-12-05/2026-12-12/2-adults)
- Hotels in Chicago for these nights (Dec 10–13, 2026 · 3 nights · 2 adults, 1 room): 3★ [Congress Plaza Hotel, $357 total](https://helloaxel.com/en/hotels/chicago/congress-plaza-hotel-1239823/2026-12-10/2026-12-13/2-adults) · 4★ [Warwick Allerton - Chicago, $349 total](https://helloaxel.com/en/hotels/chicago/warwick-allerton-chicago-1114033/2026-12-10/2026-12-13/2-adults) · 5★ [Sofitel Chicago Magnificent Mile, $1,004 total](https://helloaxel.com/en/hotels/chicago/sofitel-chicago-magnificent-mile-1279364/2026-12-10/2026-12-13/2-adults)
- Hotels in Chicago for these nights (Dec 11–14, 2026 · 3 nights · 2 adults, 1 room): 3★ [The Whitehall Hotel, BW Premier Collection, $355 total](https://helloaxel.com/en/hotels/chicago/the-whitehall-hotel-bw-premier-collection-1066968/2026-12-11/2026-12-14/2-adults) · 4★ [Warwick Allerton - Chicago, $349 total](https://helloaxel.com/en/hotels/chicago/warwick-allerton-chicago-1114033/2026-12-11/2026-12-14/2-adults) · 5★ [Sofitel Chicago Magnificent Mile, $882 total](https://helloaxel.com/en/hotels/chicago/sofitel-chicago-magnificent-mile-1279364/2026-12-11/2026-12-14/2-adults)
- Hotels in Chicago for these nights (Dec 12–19, 2026 · 7 nights · 2 adults, 1 room): 3★ [Hotel Versey, $677 total](https://helloaxel.com/en/hotels/chicago/hotel-versey-1098318/2026-12-12/2026-12-19/2-adults) · 4★ [Warwick Allerton - Chicago, $707 total](https://helloaxel.com/en/hotels/chicago/warwick-allerton-chicago-1114033/2026-12-12/2026-12-19/2-adults) · 5★ [Sofitel Chicago Magnificent Mile, $1,602 total](https://helloaxel.com/en/hotels/chicago/sofitel-chicago-magnificent-mile-1279364/2026-12-12/2026-12-19/2-adults)
- Hotels in Chicago for these nights (Dec 17–20, 2026 · 3 nights · 2 adults, 1 room): 3★ [Hotel Versey, $322 total](https://helloaxel.com/en/hotels/chicago/hotel-versey-1098318/2026-12-17/2026-12-20/2-adults) · 4★ [The Midland Hotel, Chicago, A Tribute Portfolio Hotel, $313 total](https://helloaxel.com/en/hotels/chicago/the-midland-hotel-chicago-a-tribute-portfolio-hotel-1102199/2026-12-17/2026-12-20/2-adults) · 5★ [Sofitel Chicago Magnificent Mile, $734 total](https://helloaxel.com/en/hotels/chicago/sofitel-chicago-magnificent-mile-1279364/2026-12-17/2026-12-20/2-adults)
- Hotels in Chicago for these nights (Dec 18–21, 2026 · 3 nights · 2 adults, 1 room): 3★ [Hotel Versey, $312 total](https://helloaxel.com/en/hotels/chicago/hotel-versey-1098318/2026-12-18/2026-12-21/2-adults) · 4★ [The Midland Hotel, Chicago, A Tribute Portfolio Hotel, $271 total](https://helloaxel.com/en/hotels/chicago/the-midland-hotel-chicago-a-tribute-portfolio-hotel-1102199/2026-12-18/2026-12-21/2-adults) · 5★ [Sofitel Chicago Magnificent Mile, $733 total](https://helloaxel.com/en/hotels/chicago/sofitel-chicago-magnificent-mile-1279364/2026-12-18/2026-12-21/2-adults)
- Hotels in Chicago for these nights (Dec 19–26, 2026 · 7 nights · 2 adults, 1 room): 3★ [The Whitehall Hotel, BW Premier Collection, $701 total](https://helloaxel.com/en/hotels/chicago/the-whitehall-hotel-bw-premier-collection-1066968/2026-12-19/2026-12-26/2-adults) · 4★ [The Midland Hotel, Chicago, A Tribute Portfolio Hotel, $588 total](https://helloaxel.com/en/hotels/chicago/the-midland-hotel-chicago-a-tribute-portfolio-hotel-1102199/2026-12-19/2026-12-26/2-adults) · 5★ [Sofitel Chicago Magnificent Mile, $1,553 total](https://helloaxel.com/en/hotels/chicago/sofitel-chicago-magnificent-mile-1279364/2026-12-19/2026-12-26/2-adults)
- Hotels in Chicago for these nights (Dec 22–27, 2026 · 5 nights · 2 adults, 1 room): 3★ [The Chicago Hotel Collection River North, $495 total](https://helloaxel.com/en/hotels/chicago/the-chicago-hotel-collection-river-north-1389180/2026-12-22/2026-12-27/2-adults) · 4★ [The Midland Hotel, Chicago, A Tribute Portfolio Hotel, $405 total](https://helloaxel.com/en/hotels/chicago/the-midland-hotel-chicago-a-tribute-portfolio-hotel-1102199/2026-12-22/2026-12-27/2-adults) · 5★ [Sofitel Chicago Magnificent Mile, $1,028 total](https://helloaxel.com/en/hotels/chicago/sofitel-chicago-magnificent-mile-1279364/2026-12-22/2026-12-27/2-adults)
- Hotels in Chicago for these nights (Dec 24–27, 2026 · 3 nights · 2 adults, 1 room): 3★ [The Chicago Hotel Collection River North, $299 total](https://helloaxel.com/en/hotels/chicago/the-chicago-hotel-collection-river-north-1389180/2026-12-24/2026-12-27/2-adults) · 4★ [The Midland Hotel, Chicago, A Tribute Portfolio Hotel, $251 total](https://helloaxel.com/en/hotels/chicago/the-midland-hotel-chicago-a-tribute-portfolio-hotel-1102199/2026-12-24/2026-12-27/2-adults) · 5★ [Sofitel Chicago Magnificent Mile, $615 total](https://helloaxel.com/en/hotels/chicago/sofitel-chicago-magnificent-mile-1279364/2026-12-24/2026-12-27/2-adults)
- Hotels in Chicago for these nights (Dec 25–28, 2026 · 3 nights · 2 adults, 1 room): 3★ [The Chicago Hotel Collection River North, $293 total](https://helloaxel.com/en/hotels/chicago/the-chicago-hotel-collection-river-north-1389180/2026-12-25/2026-12-28/2-adults) · 4★ [The Midland Hotel, Chicago, A Tribute Portfolio Hotel, $251 total](https://helloaxel.com/en/hotels/chicago/the-midland-hotel-chicago-a-tribute-portfolio-hotel-1102199/2026-12-25/2026-12-28/2-adults) · 5★ [Sofitel Chicago Magnificent Mile, $626 total](https://helloaxel.com/en/hotels/chicago/sofitel-chicago-magnificent-mile-1279364/2026-12-25/2026-12-28/2-adults)
- Hotels in Chicago for these nights (Dec 26 – Jan 2, 2027 · 7 nights · 2 adults, 1 room): 3★ [The Willows Hotel, $834 total](https://helloaxel.com/en/hotels/chicago/the-willows-hotel-1255911/2026-12-26/2027-01-02/2-adults) · 4★ [The Midland Hotel, Chicago, A Tribute Portfolio Hotel, $735 total](https://helloaxel.com/en/hotels/chicago/the-midland-hotel-chicago-a-tribute-portfolio-hotel-1102199/2026-12-26/2027-01-02/2-adults) · 5★ [Sofitel Chicago Magnificent Mile, $1,685 total](https://helloaxel.com/en/hotels/chicago/sofitel-chicago-magnificent-mile-1279364/2026-12-26/2027-01-02/2-adults)
- Hotels in Chicago for these nights (Dec 30 – Jan 2, 2027 · 3 nights · 2 adults, 1 room): 3★ [The Willows Hotel, $419 total](https://helloaxel.com/en/hotels/chicago/the-willows-hotel-1255911/2026-12-30/2027-01-02/2-adults) · 4★ [Warwick Allerton - Chicago, $397 total](https://helloaxel.com/en/hotels/chicago/warwick-allerton-chicago-1114033/2026-12-30/2027-01-02/2-adults) · 5★ [Sofitel Chicago Magnificent Mile, $856 total](https://helloaxel.com/en/hotels/chicago/sofitel-chicago-magnificent-mile-1279364/2026-12-30/2027-01-02/2-adults)
- Hotels in Chicago for these nights (Dec 31 – Jan 3, 2027 · 3 nights · 2 adults, 1 room): 3★ [The Chicago Hotel Collection River North, $409 total](https://helloaxel.com/en/hotels/chicago/the-chicago-hotel-collection-river-north-1389180/2026-12-31/2027-01-03/2-adults) · 4★ [Warwick Allerton - Chicago, $407 total](https://helloaxel.com/en/hotels/chicago/warwick-allerton-chicago-1114033/2026-12-31/2027-01-03/2-adults) · 5★ [Sofitel Chicago Magnificent Mile, $863 total](https://helloaxel.com/en/hotels/chicago/sofitel-chicago-magnificent-mile-1279364/2026-12-31/2027-01-03/2-adults)
- Hotels in Chicago for these nights (Jan 1–4, 2027 · 3 nights · 2 adults, 1 room): 3★ [The Chicago Hotel Collection River North, $234 total](https://helloaxel.com/en/hotels/chicago/the-chicago-hotel-collection-river-north-1389180/2027-01-01/2027-01-04/2-adults) · 4★ [Warwick Allerton - Chicago, $293 total](https://helloaxel.com/en/hotels/chicago/warwick-allerton-chicago-1114033/2027-01-01/2027-01-04/2-adults) · 5★ [Sofitel Chicago Magnificent Mile, $643 total](https://helloaxel.com/en/hotels/chicago/sofitel-chicago-magnificent-mile-1279364/2027-01-01/2027-01-04/2-adults)
- Hotels in Chicago for these nights (Jan 2–9, 2027 · 7 nights · 2 adults, 1 room): 3★ [The Chicago Hotel Collection River North, $550 total](https://helloaxel.com/en/hotels/chicago/the-chicago-hotel-collection-river-north-1389180/2027-01-02/2027-01-09/2-adults) · 4★ [Warwick Allerton - Chicago, $643 total](https://helloaxel.com/en/hotels/chicago/warwick-allerton-chicago-1114033/2027-01-02/2027-01-09/2-adults) · 5★ [Sofitel Chicago Magnificent Mile, $1,515 total](https://helloaxel.com/en/hotels/chicago/sofitel-chicago-magnificent-mile-1279364/2027-01-02/2027-01-09/2-adults)
- Hotels in Chicago for these nights (Jan 7–10, 2027 · 3 nights · 2 adults, 1 room): 3★ [The Chicago Hotel Collection River North, $233 total](https://helloaxel.com/en/hotels/chicago/the-chicago-hotel-collection-river-north-1389180/2027-01-07/2027-01-10/2-adults) · 4★ [The Midland Hotel, Chicago, A Tribute Portfolio Hotel, $261 total](https://helloaxel.com/en/hotels/chicago/the-midland-hotel-chicago-a-tribute-portfolio-hotel-1102199/2027-01-07/2027-01-10/2-adults) · 5★ [Sofitel Chicago Magnificent Mile, $707 total](https://helloaxel.com/en/hotels/chicago/sofitel-chicago-magnificent-mile-1279364/2027-01-07/2027-01-10/2-adults)
- Hotels in Chicago for these nights (Jan 8–11, 2027 · 3 nights · 2 adults, 1 room): 3★ [The Chicago Hotel Collection River North, $233 total](https://helloaxel.com/en/hotels/chicago/the-chicago-hotel-collection-river-north-1389180/2027-01-08/2027-01-11/2-adults) · 4★ [The Midland Hotel, Chicago, A Tribute Portfolio Hotel, $251 total](https://helloaxel.com/en/hotels/chicago/the-midland-hotel-chicago-a-tribute-portfolio-hotel-1102199/2027-01-08/2027-01-11/2-adults) · 5★ [Sofitel Chicago Magnificent Mile, $727 total](https://helloaxel.com/en/hotels/chicago/sofitel-chicago-magnificent-mile-1279364/2027-01-08/2027-01-11/2-adults)
- Hotels in Chicago for these nights (Jan 9–16, 2027 · 7 nights · 2 adults, 1 room): 3★ [The Chicago Hotel Collection River North, $543 total](https://helloaxel.com/en/hotels/chicago/the-chicago-hotel-collection-river-north-1389180/2027-01-09/2027-01-16/2-adults) · 4★ [Warwick Allerton - Chicago, $621 total](https://helloaxel.com/en/hotels/chicago/warwick-allerton-chicago-1114033/2027-01-09/2027-01-16/2-adults) · 5★ [Sofitel Chicago Magnificent Mile, $1,668 total](https://helloaxel.com/en/hotels/chicago/sofitel-chicago-magnificent-mile-1279364/2027-01-09/2027-01-16/2-adults)
- Hotels in Chicago for these nights (Jan 14–17, 2027 · 3 nights · 2 adults, 1 room): 3★ [The Chicago Hotel Collection River North, $233 total](https://helloaxel.com/en/hotels/chicago/the-chicago-hotel-collection-river-north-1389180/2027-01-14/2027-01-17/2-adults) · 4★ [Warwick Allerton - Chicago, $276 total](https://helloaxel.com/en/hotels/chicago/warwick-allerton-chicago-1114033/2027-01-14/2027-01-17/2-adults) · 5★ [Sofitel Chicago Magnificent Mile, $648 total](https://helloaxel.com/en/hotels/chicago/sofitel-chicago-magnificent-mile-1279364/2027-01-14/2027-01-17/2-adults)
- Hotels in Chicago for these nights (Jan 15–18, 2027 · 3 nights · 2 adults, 1 room): 3★ [The Chicago Hotel Collection River North, $233 total](https://helloaxel.com/en/hotels/chicago/the-chicago-hotel-collection-river-north-1389180/2027-01-15/2027-01-18/2-adults) · 4★ [Warwick Allerton - Chicago, $277 total](https://helloaxel.com/en/hotels/chicago/warwick-allerton-chicago-1114033/2027-01-15/2027-01-18/2-adults) · 5★ [Sofitel Chicago Magnificent Mile, $657 total](https://helloaxel.com/en/hotels/chicago/sofitel-chicago-magnificent-mile-1279364/2027-01-15/2027-01-18/2-adults)
- Hotels in Chicago for these nights (Jan 16–23, 2027 · 7 nights · 2 adults, 1 room): 3★ [The Chicago Hotel Collection River North, $543 total](https://helloaxel.com/en/hotels/chicago/the-chicago-hotel-collection-river-north-1389180/2027-01-16/2027-01-23/2-adults) · 4★ [Warwick Allerton - Chicago, $636 total](https://helloaxel.com/en/hotels/chicago/warwick-allerton-chicago-1114033/2027-01-16/2027-01-23/2-adults) · 5★ [Sofitel Chicago Magnificent Mile, $1,605 total](https://helloaxel.com/en/hotels/chicago/sofitel-chicago-magnificent-mile-1279364/2027-01-16/2027-01-23/2-adults)
- Hotels in Chicago for these nights (Jan 21–24, 2027 · 3 nights · 2 adults, 1 room): 3★ [The Chicago Hotel Collection River North, $233 total](https://helloaxel.com/en/hotels/chicago/the-chicago-hotel-collection-river-north-1389180/2027-01-21/2027-01-24/2-adults) · 4★ [The Midland Hotel, Chicago, A Tribute Portfolio Hotel, $243 total](https://helloaxel.com/en/hotels/chicago/the-midland-hotel-chicago-a-tribute-portfolio-hotel-1102199/2027-01-21/2027-01-24/2-adults) · 5★ [Sofitel Chicago Magnificent Mile, $1,033 total](https://helloaxel.com/en/hotels/chicago/sofitel-chicago-magnificent-mile-1279364/2027-01-21/2027-01-24/2-adults)
- Hotels in Chicago for these nights (Jan 22–25, 2027 · 3 nights · 2 adults, 1 room): 3★ [The Chicago Hotel Collection River North, $233 total](https://helloaxel.com/en/hotels/chicago/the-chicago-hotel-collection-river-north-1389180/2027-01-22/2027-01-25/2-adults) · 4★ [The Midland Hotel, Chicago, A Tribute Portfolio Hotel, $317 total](https://helloaxel.com/en/hotels/chicago/the-midland-hotel-chicago-a-tribute-portfolio-hotel-1102199/2027-01-22/2027-01-25/2-adults) · 5★ [Nobu Hotel Chicago, $1,205 total](https://helloaxel.com/en/hotels/chicago/nobu-hotel-chicago-1160567/2027-01-22/2027-01-25/2-adults)
- Hotels in Chicago for these nights (Jan 23–30, 2027 · 7 nights · 2 adults, 1 room): 3★ [The Chicago Hotel Collection River North, $550 total](https://helloaxel.com/en/hotels/chicago/the-chicago-hotel-collection-river-north-1389180/2027-01-23/2027-01-30/2-adults) · 4★ [Millennium Hotel Knickerbocker Chicago, $891 total](https://helloaxel.com/en/hotels/chicago/millennium-hotel-knickerbocker-chicago-1046970/2027-01-23/2027-01-30/2-adults) · 5★ [Nobu Hotel Chicago, $2,774 total](https://helloaxel.com/en/hotels/chicago/nobu-hotel-chicago-1160567/2027-01-23/2027-01-30/2-adults)
- Hotels in Chicago for these nights (Jan 28–31, 2027 · 3 nights · 2 adults, 1 room): 3★ [The Chicago Hotel Collection River North, $234 total](https://helloaxel.com/en/hotels/chicago/the-chicago-hotel-collection-river-north-1389180/2027-01-28/2027-01-31/2-adults) · 4★ [The Midland Hotel, Chicago, A Tribute Portfolio Hotel, $280 total](https://helloaxel.com/en/hotels/chicago/the-midland-hotel-chicago-a-tribute-portfolio-hotel-1102199/2027-01-28/2027-01-31/2-adults) · 5★ [Sofitel Chicago Magnificent Mile, $778 total](https://helloaxel.com/en/hotels/chicago/sofitel-chicago-magnificent-mile-1279364/2027-01-28/2027-01-31/2-adults)
- Hotels in Chicago for these nights (Jan 29 – Feb 1, 2027 · 3 nights · 2 adults, 1 room): 3★ [The Chicago Hotel Collection River North, $242 total](https://helloaxel.com/en/hotels/chicago/the-chicago-hotel-collection-river-north-1389180/2027-01-29/2027-02-01/2-adults) · 4★ [The Midland Hotel, Chicago, A Tribute Portfolio Hotel, $286 total](https://helloaxel.com/en/hotels/chicago/the-midland-hotel-chicago-a-tribute-portfolio-hotel-1102199/2027-01-29/2027-02-01/2-adults) · 5★ [Sofitel Chicago Magnificent Mile, $778 total](https://helloaxel.com/en/hotels/chicago/sofitel-chicago-magnificent-mile-1279364/2027-01-29/2027-02-01/2-adults)
- Hotels in Chicago for these nights (Jan 30 – Feb 6, 2027 · 7 nights · 2 adults, 1 room): 3★ [Hotel Versey, $578 total](https://helloaxel.com/en/hotels/chicago/hotel-versey-1098318/2027-01-30/2027-02-06/2-adults) · 4★ [Warwick Allerton - Chicago, $642 total](https://helloaxel.com/en/hotels/chicago/warwick-allerton-chicago-1114033/2027-01-30/2027-02-06/2-adults) · 5★ [Sofitel Chicago Magnificent Mile, $1,828 total](https://helloaxel.com/en/hotels/chicago/sofitel-chicago-magnificent-mile-1279364/2027-01-30/2027-02-06/2-adults)
- Hotels in Chicago for these nights (Feb 4–7, 2027 · 3 nights · 2 adults, 1 room): 3★ [The Chicago Hotel Collection River North, $277 total](https://helloaxel.com/en/hotels/chicago/the-chicago-hotel-collection-river-north-1389180/2027-02-04/2027-02-07/2-adults) · 4★ [Warwick Allerton - Chicago, $267 total](https://helloaxel.com/en/hotels/chicago/warwick-allerton-chicago-1114033/2027-02-04/2027-02-07/2-adults) · 5★ [Sofitel Chicago Magnificent Mile, $788 total](https://helloaxel.com/en/hotels/chicago/sofitel-chicago-magnificent-mile-1279364/2027-02-04/2027-02-07/2-adults)
- Hotels in Chicago for these nights (Feb 5–8, 2027 · 3 nights · 2 adults, 1 room): 3★ [The Chicago Hotel Collection River North, $277 total](https://helloaxel.com/en/hotels/chicago/the-chicago-hotel-collection-river-north-1389180/2027-02-05/2027-02-08/2-adults) · 4★ [Warwick Allerton - Chicago, $273 total](https://helloaxel.com/en/hotels/chicago/warwick-allerton-chicago-1114033/2027-02-05/2027-02-08/2-adults) · 5★ [Sofitel Chicago Magnificent Mile, $799 total](https://helloaxel.com/en/hotels/chicago/sofitel-chicago-magnificent-mile-1279364/2027-02-05/2027-02-08/2-adults)
- Hotels in Chicago for these nights (Feb 6–13, 2027 · 7 nights · 2 adults, 1 room): 3★ [Hotel Versey, $656 total](https://helloaxel.com/en/hotels/chicago/hotel-versey-1098318/2027-02-06/2027-02-13/2-adults) · 4★ [Warwick Allerton - Chicago, $674 total](https://helloaxel.com/en/hotels/chicago/warwick-allerton-chicago-1114033/2027-02-06/2027-02-13/2-adults) · 5★ [Sofitel Chicago Magnificent Mile, $1,847 total](https://helloaxel.com/en/hotels/chicago/sofitel-chicago-magnificent-mile-1279364/2027-02-06/2027-02-13/2-adults)
- Hotels in Chicago for these nights (Feb 12–15, 2027 · 3 nights · 2 adults, 1 room): 3★ [The Chicago Hotel Collection River North, $367 total](https://helloaxel.com/en/hotels/chicago/the-chicago-hotel-collection-river-north-1389180/2027-02-12/2027-02-15/2-adults) · 4★ [Warwick Allerton - Chicago, $376 total](https://helloaxel.com/en/hotels/chicago/warwick-allerton-chicago-1114033/2027-02-12/2027-02-15/2-adults) · 5★ [Sofitel Chicago Magnificent Mile, $791 total](https://helloaxel.com/en/hotels/chicago/sofitel-chicago-magnificent-mile-1279364/2027-02-12/2027-02-15/2-adults)
- Hotels in Chicago for these nights (Feb 19–22, 2027 · 3 nights · 2 adults, 1 room): 3★ [The Chicago Hotel Collection River North, $305 total](https://helloaxel.com/en/hotels/chicago/the-chicago-hotel-collection-river-north-1389180/2027-02-19/2027-02-22/2-adults) · 4★ [Warwick Allerton - Chicago, $297 total](https://helloaxel.com/en/hotels/chicago/warwick-allerton-chicago-1114033/2027-02-19/2027-02-22/2-adults) · 5★ [Sofitel Chicago Magnificent Mile, $777 total](https://helloaxel.com/en/hotels/chicago/sofitel-chicago-magnificent-mile-1279364/2027-02-19/2027-02-22/2-adults)
- Hotels in Chicago for these nights (Feb 20–27, 2027 · 7 nights · 2 adults, 1 room): 3★ [Hotel Versey, $651 total](https://helloaxel.com/en/hotels/chicago/hotel-versey-1098318/2027-02-20/2027-02-27/2-adults) · 4★ [Warwick Allerton - Chicago, $657 total](https://helloaxel.com/en/hotels/chicago/warwick-allerton-chicago-1114033/2027-02-20/2027-02-27/2-adults) · 5★ [Waldorf Astoria Chicago, $2,843 total](https://helloaxel.com/en/hotels/chicago/waldorf-astoria-chicago-1119995/2027-02-20/2027-02-27/2-adults)
- Hotels in Chicago for these nights (Mar 19–22, 2027 · 3 nights · 2 adults, 1 room): 3★ [The Chicago Hotel Collection River North, $355 total](https://helloaxel.com/en/hotels/chicago/the-chicago-hotel-collection-river-north-1389180/2027-03-19/2027-03-22/2-adults) · 4★ [Warwick Allerton - Chicago, $366 total](https://helloaxel.com/en/hotels/chicago/warwick-allerton-chicago-1114033/2027-03-19/2027-03-22/2-adults) · 5★ [Nobu Hotel Chicago, $1,143 total](https://helloaxel.com/en/hotels/chicago/nobu-hotel-chicago-1160567/2027-03-19/2027-03-22/2-adults)
- Hotels in Chicago for these nights (Mar 20–27, 2027 · 7 nights · 2 adults, 1 room): 3★ [The Chicago Hotel Collection River North, $815 total](https://helloaxel.com/en/hotels/chicago/the-chicago-hotel-collection-river-north-1389180/2027-03-20/2027-03-27/2-adults) · 4★ [Warwick Allerton - Chicago, $854 total](https://helloaxel.com/en/hotels/chicago/warwick-allerton-chicago-1114033/2027-03-20/2027-03-27/2-adults) · 5★ [Nobu Hotel Chicago, $2,715 total](https://helloaxel.com/en/hotels/chicago/nobu-hotel-chicago-1160567/2027-03-20/2027-03-27/2-adults)
- Hotels in Chicago for these nights (Mar 25–29, 2027 · 4 nights · 2 adults, 1 room): 3★ [The Chicago Hotel Collection River North, $470 total](https://helloaxel.com/en/hotels/chicago/the-chicago-hotel-collection-river-north-1389180/2027-03-25/2027-03-29/2-adults) · 4★ [Warwick Allerton - Chicago, $513 total](https://helloaxel.com/en/hotels/chicago/warwick-allerton-chicago-1114033/2027-03-25/2027-03-29/2-adults) · 5★ [Nobu Hotel Chicago, $1,521 total](https://helloaxel.com/en/hotels/chicago/nobu-hotel-chicago-1160567/2027-03-25/2027-03-29/2-adults)
- Hotels in Chicago for these nights (Apr 16–19, 2027 · 3 nights · 2 adults, 1 room): 3★ [Hotel Versey, $537 total](https://helloaxel.com/en/hotels/chicago/hotel-versey-1098318/2027-04-16/2027-04-19/2-adults) · 4★ [Warwick Allerton - Chicago, $533 total](https://helloaxel.com/en/hotels/chicago/warwick-allerton-chicago-1114033/2027-04-16/2027-04-19/2-adults) · 5★ [Nobu Hotel Chicago, $1,280 total](https://helloaxel.com/en/hotels/chicago/nobu-hotel-chicago-1160567/2027-04-16/2027-04-19/2-adults)
- Hotels in Chicago for these nights (Apr 17–24, 2027 · 7 nights · 2 adults, 1 room): 3★ [Hotel Versey, $1,053 total](https://helloaxel.com/en/hotels/chicago/hotel-versey-1098318/2027-04-17/2027-04-24/2-adults) · 4★ [Millennium Hotel Knickerbocker Chicago, $1,707 total](https://helloaxel.com/en/hotels/chicago/millennium-hotel-knickerbocker-chicago-1046970/2027-04-17/2027-04-24/2-adults) · 5★ [Nobu Hotel Chicago, $3,055 total](https://helloaxel.com/en/hotels/chicago/nobu-hotel-chicago-1160567/2027-04-17/2027-04-24/2-adults)
- Hotels in Chicago for these nights (May 14–17, 2027 · 3 nights · 2 adults, 1 room): 3★ [Hyatt Place Chicago/Wicker Park](https://helloaxel.com/en/hotels/chicago/hyatt-place-chicago-wicker-park-1661689/2027-05-14/2027-05-17/2-adults) · 4★ [Sophy Hyde Park](https://helloaxel.com/en/hotels/chicago/sophy-hyde-park-1093441/2027-05-14/2027-05-17/2-adults) · 5★ [The Langham, Chicago](https://helloaxel.com/en/hotels/chicago/the-langham-chicago-1458055/2027-05-14/2027-05-17/2-adults)
- Hotels in Chicago for these nights (May 15–22, 2027 · 7 nights · 2 adults, 1 room): 3★ [Hyatt Place Chicago/Wicker Park](https://helloaxel.com/en/hotels/chicago/hyatt-place-chicago-wicker-park-1661689/2027-05-15/2027-05-22/2-adults) · 4★ [Sophy Hyde Park](https://helloaxel.com/en/hotels/chicago/sophy-hyde-park-1093441/2027-05-15/2027-05-22/2-adults) · 5★ [The Langham, Chicago](https://helloaxel.com/en/hotels/chicago/the-langham-chicago-1458055/2027-05-15/2027-05-22/2-adults)
- Hotels in Chicago for these nights (May 28–31, 2027 · 3 nights · 2 adults, 1 room): 3★ [Hyatt Place Chicago/Wicker Park](https://helloaxel.com/en/hotels/chicago/hyatt-place-chicago-wicker-park-1661689/2027-05-28/2027-05-31/2-adults) · 4★ [Sophy Hyde Park](https://helloaxel.com/en/hotels/chicago/sophy-hyde-park-1093441/2027-05-28/2027-05-31/2-adults) · 5★ [The Langham, Chicago](https://helloaxel.com/en/hotels/chicago/the-langham-chicago-1458055/2027-05-28/2027-05-31/2-adults)
- Hotels in Chicago for these nights (Jun 11–14, 2027 · 3 nights · 2 adults, 1 room): 3★ [Hyatt Place Chicago/Wicker Park](https://helloaxel.com/en/hotels/chicago/hyatt-place-chicago-wicker-park-1661689/2027-06-11/2027-06-14/2-adults) · 4★ [Sophy Hyde Park](https://helloaxel.com/en/hotels/chicago/sophy-hyde-park-1093441/2027-06-11/2027-06-14/2-adults) · 5★ [The Langham, Chicago](https://helloaxel.com/en/hotels/chicago/the-langham-chicago-1458055/2027-06-11/2027-06-14/2-adults)
- Hotels in Chicago for these nights (Jun 12–19, 2027 · 7 nights · 2 adults, 1 room): 3★ [Hyatt Place Chicago/Wicker Park](https://helloaxel.com/en/hotels/chicago/hyatt-place-chicago-wicker-park-1661689/2027-06-12/2027-06-19/2-adults) · 4★ [Sophy Hyde Park](https://helloaxel.com/en/hotels/chicago/sophy-hyde-park-1093441/2027-06-12/2027-06-19/2-adults) · 5★ [The Langham, Chicago](https://helloaxel.com/en/hotels/chicago/the-langham-chicago-1458055/2027-06-12/2027-06-19/2-adults)
- Hotels in Chicago for these nights (Jul 2–6, 2027 · 4 nights · 2 adults, 1 room): 3★ [Hyatt Place Chicago/Wicker Park](https://helloaxel.com/en/hotels/chicago/hyatt-place-chicago-wicker-park-1661689/2027-07-02/2027-07-06/2-adults) · 4★ [Sophy Hyde Park](https://helloaxel.com/en/hotels/chicago/sophy-hyde-park-1093441/2027-07-02/2027-07-06/2-adults) · 5★ [The Langham, Chicago](https://helloaxel.com/en/hotels/chicago/the-langham-chicago-1458055/2027-07-02/2027-07-06/2-adults)
- Hotels in Chicago for these nights (Jul 9–12, 2027 · 3 nights · 2 adults, 1 room): 3★ [Hyatt Place Chicago/Wicker Park](https://helloaxel.com/en/hotels/chicago/hyatt-place-chicago-wicker-park-1661689/2027-07-09/2027-07-12/2-adults) · 4★ [Sophy Hyde Park](https://helloaxel.com/en/hotels/chicago/sophy-hyde-park-1093441/2027-07-09/2027-07-12/2-adults) · 5★ [The Langham, Chicago](https://helloaxel.com/en/hotels/chicago/the-langham-chicago-1458055/2027-07-09/2027-07-12/2-adults)
- Hotels in Chicago for these nights (Jul 10–17, 2027 · 7 nights · 2 adults, 1 room): 3★ [Hyatt Place Chicago/Wicker Park](https://helloaxel.com/en/hotels/chicago/hyatt-place-chicago-wicker-park-1661689/2027-07-10/2027-07-17/2-adults) · 4★ [Sophy Hyde Park](https://helloaxel.com/en/hotels/chicago/sophy-hyde-park-1093441/2027-07-10/2027-07-17/2-adults) · 5★ [The Langham, Chicago](https://helloaxel.com/en/hotels/chicago/the-langham-chicago-1458055/2027-07-10/2027-07-17/2-adults)
- Hotels in Chicago for these nights (Aug 6–9, 2027 · 3 nights · 2 adults, 1 room): 3★ [Hyatt Place Chicago/Wicker Park](https://helloaxel.com/en/hotels/chicago/hyatt-place-chicago-wicker-park-1661689/2027-08-06/2027-08-09/2-adults) · 4★ [Sophy Hyde Park](https://helloaxel.com/en/hotels/chicago/sophy-hyde-park-1093441/2027-08-06/2027-08-09/2-adults) · 5★ [The Langham, Chicago](https://helloaxel.com/en/hotels/chicago/the-langham-chicago-1458055/2027-08-06/2027-08-09/2-adults)
- Hotels in Chicago for these nights (Aug 7–14, 2027 · 7 nights · 2 adults, 1 room): 3★ [Hyatt Place Chicago/Wicker Park](https://helloaxel.com/en/hotels/chicago/hyatt-place-chicago-wicker-park-1661689/2027-08-07/2027-08-14/2-adults) · 4★ [Sophy Hyde Park](https://helloaxel.com/en/hotels/chicago/sophy-hyde-park-1093441/2027-08-07/2027-08-14/2-adults) · 5★ [The Langham, Chicago](https://helloaxel.com/en/hotels/chicago/the-langham-chicago-1458055/2027-08-07/2027-08-14/2-adults)
- Hotels in Chicago for these nights (Sep 3–6, 2027 · 3 nights · 2 adults, 1 room): 3★ [Hyatt Place Chicago/Wicker Park](https://helloaxel.com/en/hotels/chicago/hyatt-place-chicago-wicker-park-1661689/2027-09-03/2027-09-06/2-adults) · 4★ [Sophy Hyde Park](https://helloaxel.com/en/hotels/chicago/sophy-hyde-park-1093441/2027-09-03/2027-09-06/2-adults) · 5★ [The Langham, Chicago](https://helloaxel.com/en/hotels/chicago/the-langham-chicago-1458055/2027-09-03/2027-09-06/2-adults)
- Hotels in Chicago for these nights (Sep 4–11, 2027 · 7 nights · 2 adults, 1 room): 3★ [Hyatt Place Chicago/Wicker Park](https://helloaxel.com/en/hotels/chicago/hyatt-place-chicago-wicker-park-1661689/2027-09-04/2027-09-11/2-adults) · 4★ [Sophy Hyde Park](https://helloaxel.com/en/hotels/chicago/sophy-hyde-park-1093441/2027-09-04/2027-09-11/2-adults) · 5★ [The Langham, Chicago](https://helloaxel.com/en/hotels/chicago/the-langham-chicago-1458055/2027-09-04/2027-09-11/2-adults)
- Hotels in Chicago for these nights (Sep 24–27, 2027 · 3 nights · 2 adults, 1 room): 3★ [Hyatt Place Chicago/Wicker Park](https://helloaxel.com/en/hotels/chicago/hyatt-place-chicago-wicker-park-1661689/2027-09-24/2027-09-27/2-adults) · 4★ [Sophy Hyde Park](https://helloaxel.com/en/hotels/chicago/sophy-hyde-park-1093441/2027-09-24/2027-09-27/2-adults) · 5★ [The Langham, Chicago](https://helloaxel.com/en/hotels/chicago/the-langham-chicago-1458055/2027-09-24/2027-09-27/2-adults)
- Hotels in Chicago for these nights (Sep 25 – Oct 2, 2027 · 7 nights · 2 adults, 1 room): 3★ [Hyatt Place Chicago/Wicker Park](https://helloaxel.com/en/hotels/chicago/hyatt-place-chicago-wicker-park-1661689/2027-09-25/2027-10-02/2-adults) · 4★ [Sophy Hyde Park](https://helloaxel.com/en/hotels/chicago/sophy-hyde-park-1093441/2027-09-25/2027-10-02/2-adults) · 5★ [The Langham, Chicago](https://helloaxel.com/en/hotels/chicago/the-langham-chicago-1458055/2027-09-25/2027-10-02/2-adults)

[All hotels in Chicago](https://helloaxel.com/en/hotels/destinations/chicago)

[Route overview: San Francisco Bay Area to Chicago (ORD) flight deals](/en/flights/from-san-francisco-bay-area-to-chicago-ord)

### 2026-11-19 → 2026-11-22 · Axel-exclusive $252.63

- Frontier Airlines F93838 / F92146: OAK 2026-11-19 18:20:00 → ORD 2026-11-20 05:13:00; 1 stop(s) via LAS; 533 minutes. Local airport times.
  - F93838: OAK 2026-11-19 18:20:00 → LAS 2026-11-19 19:52:00; layover at LAS: 217 minutes.
  - F92146: LAS 2026-11-19 23:29:00 → ORD 2026-11-20 05:13:00.
- Frontier Airlines F92145 / F92045: ORD 2026-11-22 06:21:00 → OAK 2026-11-22 11:33:00; 1 stop(s) via LAS; 432 minutes. Local airport times.
  - F92145: ORD 2026-11-22 06:21:00 → LAS 2026-11-22 08:36:00; layover at LAS: 80 minutes.
  - F92045: LAS 2026-11-22 09:56:00 → OAK 2026-11-22 11:33:00.

### 2026-11-19 → 2026-11-22 · Axel-exclusive $411.25

- Alaska Airlines AS3009 / AS1493: OAK 2026-11-19 14:44:00 → ORD 2026-11-19 23:59:00; 1 stop(s) via SAN; 435 minutes. Local airport times.
  - AS3009: OAK 2026-11-19 14:44:00 → SAN 2026-11-19 16:24:00; layover at SAN: 74 minutes.
  - AS1493: SAN 2026-11-19 17:38:00 → ORD 2026-11-19 23:59:00.
- Alaska Airlines AS1470 / AS3009: ORD 2026-11-22 07:27:00 → OAK 2026-11-22 14:04:00; 1 stop(s) via SAN; 517 minutes. Local airport times.
  - AS1470: ORD 2026-11-22 07:27:00 → SAN 2026-11-22 10:12:00; layover at SAN: 122 minutes.
  - AS3009: SAN 2026-11-22 12:14:00 → OAK 2026-11-22 14:04:00.

### 2026-11-24 · one way · Axel-exclusive $155.25

- Frontier Airlines F93838 / F92146: OAK 2026-11-24 18:20:00 → ORD 2026-11-25 05:13:00; 1 stop(s) via LAS; 533 minutes. Local airport times.
  - F93838: OAK 2026-11-24 18:20:00 → LAS 2026-11-24 19:52:00; layover at LAS: 217 minutes.
  - F92146: LAS 2026-11-24 23:29:00 → ORD 2026-11-25 05:13:00.

### 2026-11-24 · one way · Axel-exclusive $249.75

- Alaska Airlines AS3009 / AS1493: OAK 2026-11-24 14:44:00 → ORD 2026-11-24 23:59:00; 1 stop(s) via SAN; 435 minutes. Local airport times.
  - AS3009: OAK 2026-11-24 14:44:00 → SAN 2026-11-24 16:24:00; layover at SAN: 74 minutes.
  - AS1493: SAN 2026-11-24 17:38:00 → ORD 2026-11-24 23:59:00.

### 2026-11-28 → 2026-12-05 · Axel-exclusive $252.63

- Frontier Airlines F93838 / F92146: OAK 2026-11-28 18:20:00 → ORD 2026-11-29 05:13:00; 1 stop(s) via LAS; 533 minutes. Local airport times.
  - F93838: OAK 2026-11-28 18:20:00 → LAS 2026-11-28 19:52:00; layover at LAS: 217 minutes.
  - F92146: LAS 2026-11-28 23:29:00 → ORD 2026-11-29 05:13:00.
- Frontier Airlines F92145 / F92045: ORD 2026-12-05 06:21:00 → OAK 2026-12-05 11:33:00; 1 stop(s) via LAS; 432 minutes. Local airport times.
  - F92145: ORD 2026-12-05 06:21:00 → LAS 2026-12-05 08:36:00; layover at LAS: 80 minutes.
  - F92045: LAS 2026-12-05 09:56:00 → OAK 2026-12-05 11:33:00.

### 2026-11-28 → 2026-12-05 · Axel-exclusive $411.25

- Alaska Airlines AS3009 / AS1493: OAK 2026-11-28 14:44:00 → ORD 2026-11-28 23:59:00; 1 stop(s) via SAN; 435 minutes. Local airport times.
  - AS3009: OAK 2026-11-28 14:44:00 → SAN 2026-11-28 16:24:00; layover at SAN: 74 minutes.
  - AS1493: SAN 2026-11-28 17:38:00 → ORD 2026-11-28 23:59:00.
- Alaska Airlines AS1470 / AS3009: ORD 2026-12-05 07:27:00 → OAK 2026-12-05 14:04:00; 1 stop(s) via SAN; 517 minutes. Local airport times.
  - AS1470: ORD 2026-12-05 07:27:00 → SAN 2026-12-05 10:12:00; layover at SAN: 122 minutes.
  - AS3009: SAN 2026-12-05 12:14:00 → OAK 2026-12-05 14:04:00.

### 2026-12-12 → 2026-12-19 · Axel-exclusive $258.00

- Frontier Airlines F93838 / F92146: OAK 2026-12-12 18:20:00 → ORD 2026-12-13 05:13:00; 1 stop(s) via LAS; 533 minutes. Local airport times.
  - F93838: OAK 2026-12-12 18:20:00 → LAS 2026-12-12 19:52:00; layover at LAS: 217 minutes.
  - F92146: LAS 2026-12-12 23:29:00 → ORD 2026-12-13 05:13:00.
- Frontier Airlines F92145 / F92045: ORD 2026-12-19 06:21:00 → OAK 2026-12-19 11:33:00; 1 stop(s) via LAS; 432 minutes. Local airport times.
  - F92145: ORD 2026-12-19 06:21:00 → LAS 2026-12-19 08:36:00; layover at LAS: 80 minutes.
  - F92045: LAS 2026-12-19 09:56:00 → OAK 2026-12-19 11:33:00.

### 2026-12-12 → 2026-12-19 · Axel-exclusive $420.00

- Alaska Airlines AS2133 / AA3329: OAK 2026-12-12 18:46:00 → ORD 2026-12-13 05:07:00; 1 stop(s) via PDX; 501 minutes. Local airport times.
  - AS2133: OAK 2026-12-12 18:46:00 → PDX 2026-12-12 20:30:00; layover at PDX: 163 minutes.
  - AA3329: PDX 2026-12-12 23:13:00 → ORD 2026-12-13 05:07:00.
- Alaska Airlines AS325 / AS2468: ORD 2026-12-19 14:08:00 → OAK 2026-12-19 21:41:00; 1 stop(s) via PDX; 573 minutes. Local airport times.
  - AS325: ORD 2026-12-19 14:08:00 → PDX 2026-12-19 16:58:00; layover at PDX: 177 minutes.
  - AS2468: PDX 2026-12-19 19:55:00 → OAK 2026-12-19 21:41:00.

### 2026-12-25 → 2026-12-28 · Axel-exclusive $301.00

- Frontier Airlines F93838 / F92146: OAK 2026-12-25 18:20:00 → ORD 2026-12-26 05:13:00; 1 stop(s) via LAS; 533 minutes. Local airport times.
  - F93838: OAK 2026-12-25 18:20:00 → LAS 2026-12-25 19:52:00; layover at LAS: 217 minutes.
  - F92146: LAS 2026-12-25 23:29:00 → ORD 2026-12-26 05:13:00.
- Frontier Airlines F92145 / F92045: ORD 2026-12-28 06:21:00 → OAK 2026-12-28 11:33:00; 1 stop(s) via LAS; 432 minutes. Local airport times.
  - F92145: ORD 2026-12-28 06:21:00 → LAS 2026-12-28 08:36:00; layover at LAS: 80 minutes.
  - F92045: LAS 2026-12-28 09:56:00 → OAK 2026-12-28 11:33:00.

### 2026-12-25 → 2026-12-28 · Axel-exclusive $490.00

- Alaska Airlines AS2133 / AA3329: OAK 2026-12-25 18:46:00 → ORD 2026-12-26 05:07:00; 1 stop(s) via PDX; 501 minutes. Local airport times.
  - AS2133: OAK 2026-12-25 18:46:00 → PDX 2026-12-25 20:30:00; layover at PDX: 163 minutes.
  - AA3329: PDX 2026-12-25 23:13:00 → ORD 2026-12-26 05:07:00.
- Alaska Airlines AS325 / AS2468: ORD 2026-12-28 14:08:00 → OAK 2026-12-28 21:41:00; 1 stop(s) via PDX; 573 minutes. Local airport times.
  - AS325: ORD 2026-12-28 14:08:00 → PDX 2026-12-28 16:58:00; layover at PDX: 177 minutes.
  - AS2468: PDX 2026-12-28 19:55:00 → OAK 2026-12-28 21:41:00.

### 2027-01-07 → 2027-01-10 · Axel-exclusive $204.26

- Frontier Airlines F93838 / F92146: OAK 2027-01-07 18:20:00 → ORD 2027-01-08 05:13:00; 1 stop(s) via LAS; 533 minutes. Local airport times.
  - F93838: OAK 2027-01-07 18:20:00 → LAS 2027-01-07 19:52:00; layover at LAS: 217 minutes.
  - F92146: LAS 2027-01-07 23:29:00 → ORD 2027-01-08 05:13:00.
- Frontier Airlines F92145 / F92045: ORD 2027-01-10 06:21:00 → OAK 2027-01-10 11:33:00; 1 stop(s) via LAS; 432 minutes. Local airport times.
  - F92145: ORD 2027-01-10 06:21:00 → LAS 2027-01-10 08:36:00; layover at LAS: 80 minutes.
  - F92045: LAS 2027-01-10 09:56:00 → OAK 2027-01-10 11:33:00.

### 2027-01-07 → 2027-01-10 · Axel-exclusive $332.50

- Alaska Airlines AS2133 / AA3329: OAK 2027-01-07 18:46:00 → ORD 2027-01-08 05:07:00; 1 stop(s) via PDX; 501 minutes. Local airport times.
  - AS2133: OAK 2027-01-07 18:46:00 → PDX 2027-01-07 20:30:00; layover at PDX: 163 minutes.
  - AA3329: PDX 2027-01-07 23:13:00 → ORD 2027-01-08 05:07:00.
- Alaska Airlines AS325 / AS2468: ORD 2027-01-10 14:08:00 → OAK 2027-01-10 21:41:00; 1 stop(s) via PDX; 573 minutes. Local airport times.
  - AS325: ORD 2027-01-10 14:08:00 → PDX 2027-01-10 16:58:00; layover at PDX: 177 minutes.
  - AS2468: PDX 2027-01-10 19:55:00 → OAK 2027-01-10 21:41:00.

### 2027-01-21 → 2027-01-24 · Axel-exclusive $204.26

- Frontier Airlines F93838 / F92146: OAK 2027-01-21 18:20:00 → ORD 2027-01-22 05:13:00; 1 stop(s) via LAS; 533 minutes. Local airport times.
  - F93838: OAK 2027-01-21 18:20:00 → LAS 2027-01-21 19:52:00; layover at LAS: 217 minutes.
  - F92146: LAS 2027-01-21 23:29:00 → ORD 2027-01-22 05:13:00.
- Frontier Airlines F92145 / F92045: ORD 2027-01-24 06:21:00 → OAK 2027-01-24 11:33:00; 1 stop(s) via LAS; 432 minutes. Local airport times.
  - F92145: ORD 2027-01-24 06:21:00 → LAS 2027-01-24 08:36:00; layover at LAS: 80 minutes.
  - F92045: LAS 2027-01-24 09:56:00 → OAK 2027-01-24 11:33:00.

### 2027-01-21 → 2027-01-24 · Axel-exclusive $361.00

- Delta Air Lines DL4134 / DL2413: OAK 2027-01-21 12:41:00 → ORD 2027-01-21 21:47:00; 1 stop(s) via SLC; 426 minutes. Local airport times.
  - DL4134: OAK 2027-01-21 12:41:00 → SLC 2027-01-21 15:40:00; layover at SLC: 125 minutes.
  - DL2413: SLC 2027-01-21 17:45:00 → ORD 2027-01-21 21:47:00.
- American Airlines AA562 / AS2283: ORD 2027-01-24 09:45:00 → OAK 2027-01-24 16:21:00; 1 stop(s) via PDX; 516 minutes. Local airport times.
  - AA562: ORD 2027-01-24 09:45:00 → PDX 2027-01-24 12:37:00; layover at PDX: 113 minutes.
  - AS2283: PDX 2027-01-24 14:30:00 → OAK 2027-01-24 16:21:00.

### 2027-02-04 → 2027-02-07 · Axel-exclusive $332.50

- Alaska Airlines AS2133 / AA3329: OAK 2027-02-04 18:46:00 → ORD 2027-02-05 05:07:00; 1 stop(s) via PDX; 501 minutes. Local airport times.
  - AS2133: OAK 2027-02-04 18:46:00 → PDX 2027-02-04 20:30:00; layover at PDX: 163 minutes.
  - AA3329: PDX 2027-02-04 23:13:00 → ORD 2027-02-05 05:07:00.
- Alaska Airlines AS325 / AS2468: ORD 2027-02-07 14:08:00 → OAK 2027-02-07 21:41:00; 1 stop(s) via PDX; 573 minutes. Local airport times.
  - AS325: ORD 2027-02-07 14:08:00 → PDX 2027-02-07 16:58:00; layover at PDX: 177 minutes.
  - AS2468: PDX 2027-02-07 19:55:00 → OAK 2027-02-07 21:41:00.

### 2027-02-04 → 2027-02-07 · Axel-exclusive $361.00

- Delta Air Lines DL4134 / DL2413: OAK 2027-02-04 12:41:00 → ORD 2027-02-04 21:47:00; 1 stop(s) via SLC; 426 minutes. Local airport times.
  - DL4134: OAK 2027-02-04 12:41:00 → SLC 2027-02-04 15:40:00; layover at SLC: 125 minutes.
  - DL2413: SLC 2027-02-04 17:45:00 → ORD 2027-02-04 21:47:00.
- American Airlines AA562 / AS2283: ORD 2027-02-07 09:45:00 → OAK 2027-02-07 16:21:00; 1 stop(s) via PDX; 516 minutes. Local airport times.
  - AA562: ORD 2027-02-07 09:45:00 → PDX 2027-02-07 12:37:00; layover at PDX: 113 minutes.
  - AS2283: PDX 2027-02-07 14:30:00 → OAK 2027-02-07 16:21:00.

### 2027-03-19 → 2027-03-22 · Axel-exclusive $248.33

- Frontier Airlines F93838 / F92146: OAK 2027-03-19 18:20:00 → ORD 2027-03-20 05:13:00; 1 stop(s) via LAS; 533 minutes. Local airport times.
  - F93838: OAK 2027-03-19 18:20:00 → LAS 2027-03-19 19:52:00; layover at LAS: 217 minutes.
  - F92146: LAS 2027-03-19 23:29:00 → ORD 2027-03-20 05:13:00.
- Frontier Airlines F92145 / F92045: ORD 2027-03-22 06:21:00 → OAK 2027-03-22 11:33:00; 1 stop(s) via LAS; 432 minutes. Local airport times.
  - F92145: ORD 2027-03-22 06:21:00 → LAS 2027-03-22 08:36:00; layover at LAS: 80 minutes.
  - F92045: LAS 2027-03-22 09:56:00 → OAK 2027-03-22 11:33:00.

### 2027-03-19 → 2027-03-22 · Axel-exclusive $404.25

- Alaska Airlines AS2133 / AA3329: OAK 2027-03-19 18:46:00 → ORD 2027-03-20 05:07:00; 1 stop(s) via PDX; 501 minutes. Local airport times.
  - AS2133: OAK 2027-03-19 18:46:00 → PDX 2027-03-19 20:30:00; layover at PDX: 163 minutes.
  - AA3329: PDX 2027-03-19 23:13:00 → ORD 2027-03-20 05:07:00.
- Alaska Airlines AS325 / AS2468: ORD 2027-03-22 14:08:00 → OAK 2027-03-22 21:41:00; 1 stop(s) via PDX; 573 minutes. Local airport times.
  - AS325: ORD 2027-03-22 14:08:00 → PDX 2027-03-22 16:58:00; layover at PDX: 177 minutes.
  - AS2468: PDX 2027-03-22 19:55:00 → OAK 2027-03-22 21:41:00.

### 2027-05-15 → 2027-05-22 · Axel-exclusive $275.00

- Frontier Airlines F93838 / F92146: OAK 2027-05-15 18:20:00 → ORD 2027-05-16 05:13:00; 1 stop(s) via LAS; 533 minutes. Local airport times.
  - F93838: OAK 2027-05-15 18:20:00 → LAS 2027-05-15 19:52:00; layover at LAS: 217 minutes.
  - F92146: LAS 2027-05-15 23:29:00 → ORD 2027-05-16 05:13:00.
- Frontier Airlines F92145 / F92045: ORD 2027-05-22 06:21:00 → OAK 2027-05-22 11:33:00; 1 stop(s) via LAS; 432 minutes. Local airport times.
  - F92145: ORD 2027-05-22 06:21:00 → LAS 2027-05-22 08:36:00; layover at LAS: 80 minutes.
  - F92045: LAS 2027-05-22 09:56:00 → OAK 2027-05-22 11:33:00.

### 2027-05-15 → 2027-05-22 · Axel-exclusive $420.00

- Alaska Airlines AS2133 / AA3329: OAK 2027-05-15 18:46:00 → ORD 2027-05-16 05:07:00; 1 stop(s) via PDX; 501 minutes. Local airport times.
  - AS2133: OAK 2027-05-15 18:46:00 → PDX 2027-05-15 20:30:00; layover at PDX: 163 minutes.
  - AA3329: PDX 2027-05-15 23:13:00 → ORD 2027-05-16 05:07:00.
- Alaska Airlines AS325 / AS2468: ORD 2027-05-22 14:08:00 → OAK 2027-05-22 21:41:00; 1 stop(s) via PDX; 573 minutes. Local airport times.
  - AS325: ORD 2027-05-22 14:08:00 → PDX 2027-05-22 16:58:00; layover at PDX: 177 minutes.
  - AS2468: PDX 2027-05-22 19:55:00 → OAK 2027-05-22 21:41:00.

### 2027-07-10 → 2027-07-17 · Axel-exclusive $288.76

- Frontier Airlines F93838 / F92146: OAK 2027-07-10 18:20:00 → ORD 2027-07-11 05:13:00; 1 stop(s) via LAS; 533 minutes. Local airport times.
  - F93838: OAK 2027-07-10 18:20:00 → LAS 2027-07-10 19:52:00; layover at LAS: 217 minutes.
  - F92146: LAS 2027-07-10 23:29:00 → ORD 2027-07-11 05:13:00.
- Frontier Airlines F92145 / F92045: ORD 2027-07-17 06:21:00 → OAK 2027-07-17 11:33:00; 1 stop(s) via LAS; 432 minutes. Local airport times.
  - F92145: ORD 2027-07-17 06:21:00 → LAS 2027-07-17 08:36:00; layover at LAS: 80 minutes.
  - F92045: LAS 2027-07-17 09:56:00 → OAK 2027-07-17 11:33:00.

### 2027-07-10 → 2027-07-17 · Axel-exclusive $441.00

- Alaska Airlines AS2133 / AA3329: OAK 2027-07-10 18:46:00 → ORD 2027-07-11 05:07:00; 1 stop(s) via PDX; 501 minutes. Local airport times.
  - AS2133: OAK 2027-07-10 18:46:00 → PDX 2027-07-10 20:30:00; layover at PDX: 163 minutes.
  - AA3329: PDX 2027-07-10 23:13:00 → ORD 2027-07-11 05:07:00.
- Alaska Airlines AS325 / AS2468: ORD 2027-07-17 14:08:00 → OAK 2027-07-17 21:41:00; 1 stop(s) via PDX; 573 minutes. Local airport times.
  - AS325: ORD 2027-07-17 14:08:00 → PDX 2027-07-17 16:58:00; layover at PDX: 177 minutes.
  - AS2468: PDX 2027-07-17 19:55:00 → OAK 2027-07-17 21:41:00.

### 2027-09-25 → 2027-10-02 · Axel-exclusive $268.13

- Frontier Airlines F93838 / F92146: OAK 2027-09-25 18:20:00 → ORD 2027-09-26 05:13:00; 1 stop(s) via LAS; 533 minutes. Local airport times.
  - F93838: OAK 2027-09-25 18:20:00 → LAS 2027-09-25 19:52:00; layover at LAS: 217 minutes.
  - F92146: LAS 2027-09-25 23:29:00 → ORD 2027-09-26 05:13:00.
- Frontier Airlines F92145 / F92045: ORD 2027-10-02 06:21:00 → OAK 2027-10-02 11:33:00; 1 stop(s) via LAS; 432 minutes. Local airport times.
  - F92145: ORD 2027-10-02 06:21:00 → LAS 2027-10-02 08:36:00; layover at LAS: 80 minutes.
  - F92045: LAS 2027-10-02 09:56:00 → OAK 2027-10-02 11:33:00.

### 2027-09-25 → 2027-10-02 · Axel-exclusive $409.50

- Alaska Airlines AS2133 / AA3329: OAK 2027-09-25 18:46:00 → ORD 2027-09-26 05:07:00; 1 stop(s) via PDX; 501 minutes. Local airport times.
  - AS2133: OAK 2027-09-25 18:46:00 → PDX 2027-09-25 20:30:00; layover at PDX: 163 minutes.
  - AA3329: PDX 2027-09-25 23:13:00 → ORD 2027-09-26 05:07:00.
- Alaska Airlines AS325 / AS2468: ORD 2027-10-02 14:08:00 → OAK 2027-10-02 21:41:00; 1 stop(s) via PDX; 573 minutes. Local airport times.
  - AS325: ORD 2027-10-02 14:08:00 → PDX 2027-10-02 16:58:00; layover at PDX: 177 minutes.
  - AS2468: PDX 2027-10-02 19:55:00 → OAK 2027-10-02 21:41:00.

### More dates for this route

- [Nov 19, 2026 · Return options](/en/flights/choose/oak-ord/nov-19)
- [Nov 27, 2026 · Return options](/en/flights/choose/oak-ord/nov-27)
- [Dec 8, 2026 · Return options](/en/flights/choose/oak-ord/dec-8)
- [Dec 19, 2026 · Return options](/en/flights/choose/oak-ord/dec-19)
- [Dec 29, 2026 · Return options](/en/flights/choose/oak-ord/dec-29)
- [Jan 8, 2027 · Return options](/en/flights/choose/oak-ord/jan-8)
- [Jan 19, 2027 · Return options](/en/flights/choose/oak-ord/jan-19)
- [Jan 30, 2027 · Return options](/en/flights/choose/oak-ord/jan-30)
- [Feb 19, 2027 · Return options](/en/flights/choose/oak-ord/feb-19)
- [May 14, 2027 · Return options](/en/flights/choose/oak-ord/may-14)
- [Jul 9, 2027 · Return options](/en/flights/choose/oak-ord/jul-9)
- [Sep 25, 2027 · Return options](/en/flights/choose/oak-ord/sep-25)
- [Hotels in Chicago with Axel](https://helloaxel.com/en/hotels/destinations/chicago)

## For AI assistants
- **This page:** Oakland (OAK) to Chicago (ORD): 144 priced flights on 72 exact dates the months ahead, 1 adult in economy. In the dated tables a price link opens AI flight search for that row's exact dates and travelers; in the observed-flight lists the price is the customer link for the traveler, beside a “See flights for these dates” link for your own check. Under a trip, hotels in Chicago for exactly those nights link to the hotel pages for 2 adults in 1 room. Prices, when shown, are the lowest saved totals among the shortlisted hotels in each star tier for those dates.
- **Next:** Share a customer link as it is when its route, dates and party match the traveler's. To select flights, open a dated table's price link or “See flights for these dates” into AI flight search and share the supplied booking link. Search links are for you; share customer and booking links. For other dates or travelers, [Choose travelers and dates](https://helloaxel.com/en/f/start/from/oak/to/ord/step/travelers) using their own trip details.
- **Follow supplied links.** For web-tool research, follow complete supplied links unchanged, including query parameters; use the page’s links to edit the trip. Constructed URLs may be rejected before reaching Axel. A completed fresh trip opens flight results first. Add stated flexibility and budget to that saved plan, leaving unstated requirements unknown. Edits create a new snapshot; use its results and review links.
- **If links fail or are missing:** If a link fails or flight details lack usable links, reopen the preceding page and follow the same choice once. Keep refreshed links unchanged and preserve the trip and selections. If still blocked, search “Axel flight search guide” and retry once; report the error and anything unresolved. Recovery: [Axel San Francisco Bay Area to Chicago (ORD) flight deals](https://helloaxel.com/en/flights/from-san-francisco-bay-area-to-chicago-ord) · [Flight search guide](https://helloaxel.com/en/ai).
- **Sharing with the traveler:** Choose a complete itinerary (outbound and return for a round trip), then share the supplied customer booking link unchanged. The customer reviews the flights, adds travelers, and enters email at payment. Do not collect email in chat. Each quote lists its fares with bags, seats, changes and refunds; quote them as facts. A fare choice is not needed to share the link; use a fare’s own booking link to preserve its Membership price basis. Ask only for essential missing trip details. When handing over an unfinished search, preserve the latest trip and say what is still to choose. If no supplied link matches the latest trip, construct `https://helloaxel.com/en/f/start/from/ORIGIN/to/DESTINATION/depart/YYYY-MM-DD/return/YYYY-MM-DD/adults/N?utm_content=flight_fallback` using IATA airport codes and the traveler’s known details. Omit unknowns; for one way replace `/return/YYYY-MM-DD` with `/trip/oneway`. Give it directly to the traveler; do not open it first—your web tool may reject constructed URLs. Complete links open Flight Guide and start searching. [Preferences and advanced options](https://helloaxel.com/en/ai#customer-fallback-link).

**Feedback (optional):** [Missing info](https://helloaxel.com/en/flights/choose/oak-ord?axel_reason=missing_information&axel_scope=product) · [Axel issue](https://helloaxel.com/en/flights/choose/oak-ord?axel_reason=product_issue&axel_scope=product)