# Newark (EWR) to Chicago (MDW)

Newark (EWR) to Chicago (MDW), the months ahead: 72 priced flights on 72 exact dates. 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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### Newark (EWR) to Chicago (MDW): November 2026

| Travel dates | Airline | Stops | Total price |
| --- | --- | --- | ---: |
| Nov 12, 2026 – Nov 15, 2026 · 3 nights · [Compare return dates departing Nov 12, 2026](https://helloaxel.com/en/flights/choose/ewr-mdw/nov-12) | Delta Air Lines | Up to 1 stop each way | [Axel-exclusive $320.00](https://helloaxel.com/en/f/start/from/ewr/to/mdw/depart/november-12-2026/return/november-15-2026/adults/1/cabin/economy) |
| Nov 13, 2026 – Nov 16, 2026 · 3 nights · [Compare return dates departing Nov 13, 2026](https://helloaxel.com/en/flights/choose/ewr-mdw/nov-13) | Delta Air Lines | Up to 1 stop each way | [Axel-exclusive $320.00](https://helloaxel.com/en/f/start/from/ewr/to/mdw/depart/november-13-2026/return/november-16-2026/adults/1/cabin/economy) |
| Nov 14, 2026 – Nov 21, 2026 · 7 nights · [Compare return dates departing Nov 14, 2026](https://helloaxel.com/en/flights/choose/ewr-mdw/nov-14) | Delta Air Lines | Up to 1 stop each way | [Axel-exclusive $320.00](https://helloaxel.com/en/f/start/from/ewr/to/mdw/depart/november-14-2026/return/november-21-2026/adults/1/cabin/economy) |
| Nov 17, 2026 · One way · [Compare return dates departing Nov 17, 2026](https://helloaxel.com/en/flights/choose/ewr-mdw/nov-17) | Delta Air Lines | Up to 1 stop each way | [Axel-exclusive $185.00](https://helloaxel.com/en/f/start/from/ewr/to/mdw/depart/november-17-2026/trip/one-way/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/ewr-mdw/nov-19) | Delta Air Lines | Up to 1 stop each way | [Axel-exclusive $320.00](https://helloaxel.com/en/f/start/from/ewr/to/mdw/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/ewr-mdw/nov-20) | Delta Air Lines | Up to 1 stop each way | [Axel-exclusive $320.00](https://helloaxel.com/en/f/start/from/ewr/to/mdw/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/ewr-mdw/nov-21) | Delta Air Lines | Up to 1 stop each way | [Axel-exclusive $368.00](https://helloaxel.com/en/f/start/from/ewr/to/mdw/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/ewr-mdw/nov-24) | Delta Air Lines | Up to 1 stop each way | [Axel-exclusive $240.50](https://helloaxel.com/en/f/start/from/ewr/to/mdw/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/ewr-mdw/nov-24) | Delta Air Lines | Up to 1 stop each way | [Axel-exclusive $416.00](https://helloaxel.com/en/f/start/from/ewr/to/mdw/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/ewr-mdw/nov-26) | Delta Air Lines | Up to 1 stop each way | [Axel-exclusive $416.00](https://helloaxel.com/en/f/start/from/ewr/to/mdw/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/ewr-mdw/nov-27) | Delta Air Lines | Up to 1 stop each way | [Axel-exclusive $416.00](https://helloaxel.com/en/f/start/from/ewr/to/mdw/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/ewr-mdw/nov-28) | Delta Air Lines | Up to 1 stop each way | [Axel-exclusive $368.00](https://helloaxel.com/en/f/start/from/ewr/to/mdw/depart/november-28-2026/return/december-5-2026/adults/1/cabin/economy) |

### Newark (EWR) to Chicago (MDW): 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/ewr-mdw/dec-1) | Delta Air Lines | Up to 1 stop each way | [Axel-exclusive $185.00](https://helloaxel.com/en/f/start/from/ewr/to/mdw/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/ewr-mdw/dec-3) | Delta Air Lines | Up to 1 stop each way | [Axel-exclusive $320.00](https://helloaxel.com/en/f/start/from/ewr/to/mdw/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/ewr-mdw/dec-4) | Delta Air Lines | Up to 1 stop each way | [Axel-exclusive $320.00](https://helloaxel.com/en/f/start/from/ewr/to/mdw/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/ewr-mdw/dec-5) | Delta Air Lines | Up to 1 stop each way | [Axel-exclusive $320.00](https://helloaxel.com/en/f/start/from/ewr/to/mdw/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/ewr-mdw/dec-8) | Delta Air Lines | Up to 1 stop each way | [Axel-exclusive $185.00](https://helloaxel.com/en/f/start/from/ewr/to/mdw/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/ewr-mdw/dec-10) | Delta Air Lines | Up to 1 stop each way | [Axel-exclusive $320.00](https://helloaxel.com/en/f/start/from/ewr/to/mdw/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/ewr-mdw/dec-11) | Delta Air Lines | Up to 1 stop each way | [Axel-exclusive $320.00](https://helloaxel.com/en/f/start/from/ewr/to/mdw/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/ewr-mdw/dec-12) | Delta Air Lines | Up to 1 stop each way | [Axel-exclusive $320.00](https://helloaxel.com/en/f/start/from/ewr/to/mdw/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/ewr-mdw/dec-15) | Delta Air Lines | Up to 1 stop each way | [Axel-exclusive $185.00](https://helloaxel.com/en/f/start/from/ewr/to/mdw/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/ewr-mdw/dec-17) | Delta Air Lines | Up to 1 stop each way | [Axel-exclusive $360.00](https://helloaxel.com/en/f/start/from/ewr/to/mdw/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/ewr-mdw/dec-18) | Delta Air Lines | Up to 1 stop each way | [Axel-exclusive $360.00](https://helloaxel.com/en/f/start/from/ewr/to/mdw/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/ewr-mdw/dec-19) | Delta Air Lines | Up to 1 stop each way | [Axel-exclusive $360.00](https://helloaxel.com/en/f/start/from/ewr/to/mdw/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/ewr-mdw/dec-22) | Delta Air Lines | Up to 1 stop each way | [Axel-exclusive $231.25](https://helloaxel.com/en/f/start/from/ewr/to/mdw/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/ewr-mdw/dec-22) | Delta Air Lines | Up to 1 stop each way | [Axel-exclusive $392.00](https://helloaxel.com/en/f/start/from/ewr/to/mdw/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/ewr-mdw/dec-24) | Delta Air Lines | Up to 1 stop each way | [Axel-exclusive $392.00](https://helloaxel.com/en/f/start/from/ewr/to/mdw/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/ewr-mdw/dec-25) | Delta Air Lines | Up to 1 stop each way | [Axel-exclusive $392.00](https://helloaxel.com/en/f/start/from/ewr/to/mdw/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/ewr-mdw/dec-26) | Delta Air Lines | Up to 1 stop each way | [Axel-exclusive $392.00](https://helloaxel.com/en/f/start/from/ewr/to/mdw/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/ewr-mdw/dec-29) | Delta Air Lines | Up to 1 stop each way | [Axel-exclusive $222.00](https://helloaxel.com/en/f/start/from/ewr/to/mdw/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/ewr-mdw/dec-30) | Delta Air Lines | Up to 1 stop each way | [Axel-exclusive $384.00](https://helloaxel.com/en/f/start/from/ewr/to/mdw/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/ewr-mdw/dec-31) | Delta Air Lines | Up to 1 stop each way | [Axel-exclusive $384.00](https://helloaxel.com/en/f/start/from/ewr/to/mdw/depart/december-31-2026/return/january-3-2027/adults/1/cabin/economy) |

### Newark (EWR) to Chicago (MDW): 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/ewr-mdw/jan-1) | Delta Air Lines | Up to 1 stop each way | [Axel-exclusive $352.00](https://helloaxel.com/en/f/start/from/ewr/to/mdw/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/ewr-mdw/jan-2) | Delta Air Lines | Up to 1 stop each way | [Axel-exclusive $352.00](https://helloaxel.com/en/f/start/from/ewr/to/mdw/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/ewr-mdw/jan-5) | Delta Air Lines | Up to 1 stop each way | [Axel-exclusive $185.00](https://helloaxel.com/en/f/start/from/ewr/to/mdw/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/ewr-mdw/jan-7) | Delta Air Lines | Up to 1 stop each way | [Axel-exclusive $320.00](https://helloaxel.com/en/f/start/from/ewr/to/mdw/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/ewr-mdw/jan-8) | Delta Air Lines | Up to 1 stop each way | [Axel-exclusive $320.00](https://helloaxel.com/en/f/start/from/ewr/to/mdw/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/ewr-mdw/jan-9) | Delta Air Lines | Up to 1 stop each way | [Axel-exclusive $320.00](https://helloaxel.com/en/f/start/from/ewr/to/mdw/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/ewr-mdw/jan-12) | Delta Air Lines | Up to 1 stop each way | [Axel-exclusive $185.00](https://helloaxel.com/en/f/start/from/ewr/to/mdw/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/ewr-mdw/jan-14) | Delta Air Lines | Up to 1 stop each way | [Axel-exclusive $320.00](https://helloaxel.com/en/f/start/from/ewr/to/mdw/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/ewr-mdw/jan-15) | Delta Air Lines | Up to 1 stop each way | [Axel-exclusive $320.00](https://helloaxel.com/en/f/start/from/ewr/to/mdw/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/ewr-mdw/jan-16) | Delta Air Lines | Up to 1 stop each way | [Axel-exclusive $320.00](https://helloaxel.com/en/f/start/from/ewr/to/mdw/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/ewr-mdw/jan-19) | Delta Air Lines | Up to 1 stop each way | [Axel-exclusive $185.00](https://helloaxel.com/en/f/start/from/ewr/to/mdw/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/ewr-mdw/jan-21) | Delta Air Lines | Up to 1 stop each way | [Axel-exclusive $320.00](https://helloaxel.com/en/f/start/from/ewr/to/mdw/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/ewr-mdw/jan-22) | Delta Air Lines | Up to 1 stop each way | [Axel-exclusive $320.00](https://helloaxel.com/en/f/start/from/ewr/to/mdw/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/ewr-mdw/jan-23) | Delta Air Lines | Up to 1 stop each way | [Axel-exclusive $320.00](https://helloaxel.com/en/f/start/from/ewr/to/mdw/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/ewr-mdw/jan-26) | Delta Air Lines | Up to 1 stop each way | [Axel-exclusive $185.00](https://helloaxel.com/en/f/start/from/ewr/to/mdw/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/ewr-mdw/jan-28) | Delta Air Lines | Up to 1 stop each way | [Axel-exclusive $320.00](https://helloaxel.com/en/f/start/from/ewr/to/mdw/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/ewr-mdw/jan-29) | Delta Air Lines | Up to 1 stop each way | [Axel-exclusive $320.00](https://helloaxel.com/en/f/start/from/ewr/to/mdw/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/ewr-mdw/jan-30) | Delta Air Lines | Up to 1 stop each way | [Axel-exclusive $320.00](https://helloaxel.com/en/f/start/from/ewr/to/mdw/depart/january-30-2027/return/february-6-2027/adults/1/cabin/economy) |

### Newark (EWR) to Chicago (MDW): 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/ewr-mdw/feb-2) | Delta Air Lines | Up to 1 stop each way | [Axel-exclusive $185.00](https://helloaxel.com/en/f/start/from/ewr/to/mdw/depart/february-2-2027/trip/one-way/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/ewr-mdw/feb-12) | Delta Air Lines | Up to 1 stop each way | [Axel-exclusive $320.00](https://helloaxel.com/en/f/start/from/ewr/to/mdw/depart/february-12-2027/return/february-15-2027/adults/1/cabin/economy) |
| Feb 13, 2027 – Feb 20, 2027 · 7 nights · [Compare return dates departing Feb 13, 2027](https://helloaxel.com/en/flights/choose/ewr-mdw/feb-13) | Delta Air Lines | Up to 1 stop each way | [Axel-exclusive $320.00](https://helloaxel.com/en/f/start/from/ewr/to/mdw/depart/february-13-2027/return/february-20-2027/adults/1/cabin/economy) |

### Newark (EWR) to Chicago (MDW): March 2027

| Travel dates | Airline | Stops | Total price |
| --- | --- | --- | ---: |
| Mar 12, 2027 – Mar 15, 2027 · 3 nights · [Compare return dates departing Mar 12, 2027](https://helloaxel.com/en/flights/choose/ewr-mdw/mar-12) | Delta Air Lines | Up to 1 stop each way | [Axel-exclusive $320.00](https://helloaxel.com/en/f/start/from/ewr/to/mdw/depart/march-12-2027/return/march-15-2027/adults/1/cabin/economy) |
| Mar 13, 2027 – Mar 20, 2027 · 7 nights · [Compare return dates departing Mar 13, 2027](https://helloaxel.com/en/flights/choose/ewr-mdw/mar-13) | Delta Air Lines | Up to 1 stop each way | [Axel-exclusive $320.00](https://helloaxel.com/en/f/start/from/ewr/to/mdw/depart/march-13-2027/return/march-20-2027/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/ewr-mdw/mar-25) | Delta Air Lines | Up to 1 stop each way | [Axel-exclusive $335.00](https://helloaxel.com/en/f/start/from/ewr/to/mdw/depart/march-25-2027/return/march-29-2027/adults/1/cabin/economy) |

### Newark (EWR) to Chicago (MDW): April 2027

| Travel dates | Airline | Stops | Total price |
| --- | --- | --- | ---: |
| Apr 9, 2027 – Apr 12, 2027 · 3 nights · [Compare return dates departing Apr 9, 2027](https://helloaxel.com/en/flights/choose/ewr-mdw/apr-9) | Delta Air Lines | Up to 1 stop each way | [Axel-exclusive $350.00](https://helloaxel.com/en/f/start/from/ewr/to/mdw/depart/april-9-2027/return/april-12-2027/adults/1/cabin/economy) |
| Apr 10, 2027 – Apr 17, 2027 · 7 nights · [Compare return dates departing Apr 10, 2027](https://helloaxel.com/en/flights/choose/ewr-mdw/apr-10) | Delta Air Lines | Up to 1 stop each way | [Axel-exclusive $350.00](https://helloaxel.com/en/f/start/from/ewr/to/mdw/depart/april-10-2027/return/april-17-2027/adults/1/cabin/economy) |

### Newark (EWR) to Chicago (MDW): May 2027

| Travel dates | Airline | Stops | Total price |
| --- | --- | --- | ---: |
| May 7, 2027 – May 10, 2027 · 3 nights · [Compare return dates departing May 7, 2027](https://helloaxel.com/en/flights/choose/ewr-mdw/may-7) | Delta Air Lines | Up to 1 stop each way | [Axel-exclusive $350.00](https://helloaxel.com/en/f/start/from/ewr/to/mdw/depart/may-7-2027/return/may-10-2027/adults/1/cabin/economy) |
| May 8, 2027 – May 15, 2027 · 7 nights · [Compare return dates departing May 8, 2027](https://helloaxel.com/en/flights/choose/ewr-mdw/may-8) | Delta Air Lines | Up to 1 stop each way | [Axel-exclusive $350.00](https://helloaxel.com/en/f/start/from/ewr/to/mdw/depart/may-8-2027/return/may-15-2027/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/ewr-mdw/may-28) | Delta Air Lines | Up to 1 stop each way | [Axel-exclusive $385.00](https://helloaxel.com/en/f/start/from/ewr/to/mdw/depart/may-28-2027/return/may-31-2027/adults/1/cabin/economy) |

### Newark (EWR) to Chicago (MDW): June 2027

| Travel dates | Airline | Stops | Total price |
| --- | --- | --- | ---: |
| Jun 4, 2027 – Jun 7, 2027 · 3 nights · [Compare return dates departing Jun 4, 2027](https://helloaxel.com/en/flights/choose/ewr-mdw/jun-4) | Delta Air Lines | Up to 1 stop each way | [Axel-exclusive $350.00](https://helloaxel.com/en/f/start/from/ewr/to/mdw/depart/june-4-2027/return/june-7-2027/adults/1/cabin/economy) |
| Jun 5, 2027 – Jun 12, 2027 · 7 nights · [Compare return dates departing Jun 5, 2027](https://helloaxel.com/en/flights/choose/ewr-mdw/jun-5) | Delta Air Lines | Up to 1 stop each way | [Axel-exclusive $350.00](https://helloaxel.com/en/f/start/from/ewr/to/mdw/depart/june-5-2027/return/june-12-2027/adults/1/cabin/economy) |

### Newark (EWR) to Chicago (MDW): July 2027

| Travel dates | Airline | Stops | Total price |
| --- | --- | --- | ---: |
| Jul 2, 2027 – Jul 5, 2027 · 3 nights · [Compare return dates departing Jul 2, 2027](https://helloaxel.com/en/flights/choose/ewr-mdw/jul-2) | Delta Air Lines | Up to 1 stop each way | [Axel-exclusive $402.50](https://helloaxel.com/en/f/start/from/ewr/to/mdw/depart/july-2-2027/return/july-5-2027/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/ewr-mdw/jul-2) | Delta Air Lines | Up to 1 stop each way | [Axel-exclusive $402.50](https://helloaxel.com/en/f/start/from/ewr/to/mdw/depart/july-2-2027/return/july-6-2027/adults/1/cabin/economy) |
| Jul 3, 2027 – Jul 10, 2027 · 7 nights · [Compare return dates departing Jul 3, 2027](https://helloaxel.com/en/flights/choose/ewr-mdw/jul-3) | Delta Air Lines | Up to 1 stop each way | [Axel-exclusive $376.25](https://helloaxel.com/en/f/start/from/ewr/to/mdw/depart/july-3-2027/return/july-10-2027/adults/1/cabin/economy) |
| Jul 30, 2027 – Aug 2, 2027 · 3 nights · [Compare return dates departing Jul 30, 2027](https://helloaxel.com/en/flights/choose/ewr-mdw/jul-30) | Delta Air Lines | Up to 1 stop each way | [Axel-exclusive $350.00](https://helloaxel.com/en/f/start/from/ewr/to/mdw/depart/july-30-2027/return/august-2-2027/adults/1/cabin/economy) |
| Jul 31, 2027 – Aug 7, 2027 · 7 nights · [Compare return dates departing Jul 31, 2027](https://helloaxel.com/en/flights/choose/ewr-mdw/jul-31) | Delta Air Lines | Up to 1 stop each way | [Axel-exclusive $350.00](https://helloaxel.com/en/f/start/from/ewr/to/mdw/depart/july-31-2027/return/august-7-2027/adults/1/cabin/economy) |

### Newark (EWR) to Chicago (MDW): August 2027

| Travel dates | Airline | Stops | Total price |
| --- | --- | --- | ---: |
| Aug 27, 2027 – Aug 30, 2027 · 3 nights · [Compare return dates departing Aug 27, 2027](https://helloaxel.com/en/flights/choose/ewr-mdw/aug-27) | Delta Air Lines | Up to 1 stop each way | [Axel-exclusive $350.00](https://helloaxel.com/en/f/start/from/ewr/to/mdw/depart/august-27-2027/return/august-30-2027/adults/1/cabin/economy) |
| Aug 28, 2027 – Sep 4, 2027 · 7 nights · [Compare return dates departing Aug 28, 2027](https://helloaxel.com/en/flights/choose/ewr-mdw/aug-28) | Delta Air Lines | Up to 1 stop each way | [Axel-exclusive $367.50](https://helloaxel.com/en/f/start/from/ewr/to/mdw/depart/august-28-2027/return/september-4-2027/adults/1/cabin/economy) |

### Newark (EWR) to Chicago (MDW): 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/ewr-mdw/sep-3) | Delta Air Lines | Up to 1 stop each way | [Axel-exclusive $385.00](https://helloaxel.com/en/f/start/from/ewr/to/mdw/depart/september-3-2027/return/september-6-2027/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/ewr-mdw/sep-24) | Delta Air Lines | Up to 1 stop each way | [Axel-exclusive $350.00](https://helloaxel.com/en/f/start/from/ewr/to/mdw/depart/september-24-2027/return/september-27-2027/adults/1/cabin/economy) |

### Hotels in Chicago for these trips

**Hotels:** under a trip, hotels in Chicago for exactly those nights: the lowest 3★, 4★, 5★ stay totals among the city's featured hotels, Axel's price for 2 adults in 1 room, each opening that hotel's page for those dates with the rooms and the booking link.

- Hotels in Chicago for these nights (Nov 12–15, 2026 · 3 nights · 2 adults, 1 room): 3★ [Chicago Lake Shore Hotel, $476 total](https://helloaxel.com/en/hotels/chicago/chicago-lake-shore-hotel-1255283/2026-11-12/2026-11-15/2-adults) · 4★ [The Talbott, Autograph Collection, $721 total](https://helloaxel.com/en/hotels/chicago/the-talbott-autograph-collection-1104923/2026-11-12/2026-11-15/2-adults) · 5★ [Nobu Hotel Chicago, $1,586 total](https://helloaxel.com/en/hotels/chicago/nobu-hotel-chicago-1160567/2026-11-12/2026-11-15/2-adults)
- Hotels in Chicago for these nights (Nov 13–16, 2026 · 3 nights · 2 adults, 1 room): 3★ [Chicago Lake Shore Hotel, $468 total](https://helloaxel.com/en/hotels/chicago/chicago-lake-shore-hotel-1255283/2026-11-13/2026-11-16/2-adults) · 4★ [The Talbott, Autograph Collection, $698 total](https://helloaxel.com/en/hotels/chicago/the-talbott-autograph-collection-1104923/2026-11-13/2026-11-16/2-adults) · 5★ [Nobu Hotel Chicago, $1,445 total](https://helloaxel.com/en/hotels/chicago/nobu-hotel-chicago-1160567/2026-11-13/2026-11-16/2-adults)
- Hotels in Chicago for these nights (Nov 14–21, 2026 · 7 nights · 2 adults, 1 room): 3★ [Chicago Lake Shore Hotel, $1,052 total](https://helloaxel.com/en/hotels/chicago/chicago-lake-shore-hotel-1255283/2026-11-14/2026-11-21/2-adults) · 4★ [Holiday Inn Chicago Dwtn - Wolf Point, $1,695 total](https://helloaxel.com/en/hotels/chicago/holiday-inn-chicago-dwtn-wolf-point-1399165/2026-11-14/2026-11-21/2-adults) · 5★ [Nobu Hotel Chicago, $3,461 total](https://helloaxel.com/en/hotels/chicago/nobu-hotel-chicago-1160567/2026-11-14/2026-11-21/2-adults)
- Hotels in Chicago for these nights (Nov 19–22, 2026 · 3 nights · 2 adults, 1 room): 3★ [The Willows Hotel, $575 total](https://helloaxel.com/en/hotels/chicago/the-willows-hotel-1255911/2026-11-19/2026-11-22/2-adults) · 4★ [Claridge House Chicago, Tapestry Collection by Hilton, $650 total](https://helloaxel.com/en/hotels/chicago/claridge-house-chicago-tapestry-collection-by-hilton-1096118/2026-11-19/2026-11-22/2-adults) · 5★ [Nobu Hotel Chicago, $1,410 total](https://helloaxel.com/en/hotels/chicago/nobu-hotel-chicago-1160567/2026-11-19/2026-11-22/2-adults)
- Hotels in Chicago for these nights (Nov 20–23, 2026 · 3 nights · 2 adults, 1 room): 3★ [The Willows Hotel, $521 total](https://helloaxel.com/en/hotels/chicago/the-willows-hotel-1255911/2026-11-20/2026-11-23/2-adults) · 4★ [Holiday Inn Chicago Dwtn - Wolf Point, $601 total](https://helloaxel.com/en/hotels/chicago/holiday-inn-chicago-dwtn-wolf-point-1399165/2026-11-20/2026-11-23/2-adults) · 5★ [Nobu Hotel Chicago, $1,262 total](https://helloaxel.com/en/hotels/chicago/nobu-hotel-chicago-1160567/2026-11-20/2026-11-23/2-adults)
- Hotels in Chicago for these nights (Nov 21–28, 2026 · 7 nights · 2 adults, 1 room): 3★ [Chicago Lake Shore Hotel, $934 total](https://helloaxel.com/en/hotels/chicago/chicago-lake-shore-hotel-1255283/2026-11-21/2026-11-28/2-adults) · 4★ [Holiday Inn Chicago Dwtn - Wolf Point, $1,090 total](https://helloaxel.com/en/hotels/chicago/holiday-inn-chicago-dwtn-wolf-point-1399165/2026-11-21/2026-11-28/2-adults) · 5★ [Nobu Hotel Chicago, $2,423 total](https://helloaxel.com/en/hotels/chicago/nobu-hotel-chicago-1160567/2026-11-21/2026-11-28/2-adults)
- Hotels in Chicago for these nights (Nov 24–29, 2026 · 5 nights · 2 adults, 1 room): 3★ [Chicago Lake Shore Hotel, $637 total](https://helloaxel.com/en/hotels/chicago/chicago-lake-shore-hotel-1255283/2026-11-24/2026-11-29/2-adults) · 4★ [Holiday Inn Chicago Dwtn - Wolf Point, $769 total](https://helloaxel.com/en/hotels/chicago/holiday-inn-chicago-dwtn-wolf-point-1399165/2026-11-24/2026-11-29/2-adults) · 5★ [Nobu Hotel Chicago, $1,694 total](https://helloaxel.com/en/hotels/chicago/nobu-hotel-chicago-1160567/2026-11-24/2026-11-29/2-adults)
- Hotels in Chicago for these nights (Nov 26–29, 2026 · 3 nights · 2 adults, 1 room): 3★ [Chicago Lake Shore Hotel, $411 total](https://helloaxel.com/en/hotels/chicago/chicago-lake-shore-hotel-1255283/2026-11-26/2026-11-29/2-adults) · 4★ [Holiday Inn Chicago Dwtn - Wolf Point, $506 total](https://helloaxel.com/en/hotels/chicago/holiday-inn-chicago-dwtn-wolf-point-1399165/2026-11-26/2026-11-29/2-adults) · 5★ [Nobu Hotel Chicago, $1,050 total](https://helloaxel.com/en/hotels/chicago/nobu-hotel-chicago-1160567/2026-11-26/2026-11-29/2-adults)
- Hotels in Chicago for these nights (Nov 27–30, 2026 · 3 nights · 2 adults, 1 room): 3★ [Chicago Lake Shore Hotel, $409 total](https://helloaxel.com/en/hotels/chicago/chicago-lake-shore-hotel-1255283/2026-11-27/2026-11-30/2-adults) · 4★ [Holiday Inn Chicago Dwtn - Wolf Point, $541 total](https://helloaxel.com/en/hotels/chicago/holiday-inn-chicago-dwtn-wolf-point-1399165/2026-11-27/2026-11-30/2-adults) · 5★ [Nobu Hotel Chicago, $1,120 total](https://helloaxel.com/en/hotels/chicago/nobu-hotel-chicago-1160567/2026-11-27/2026-11-30/2-adults)
- Hotels in Chicago for these nights (Nov 28 – Dec 5, 2026 · 7 nights · 2 adults, 1 room): 3★ [The Willows Hotel, $836 total](https://helloaxel.com/en/hotels/chicago/the-willows-hotel-1255911/2026-11-28/2026-12-05/2-adults) · 4★ [Claridge House Chicago, Tapestry Collection by Hilton, $1,293 total](https://helloaxel.com/en/hotels/chicago/claridge-house-chicago-tapestry-collection-by-hilton-1096118/2026-11-28/2026-12-05/2-adults) · 5★ [Nobu Hotel Chicago, $2,976.50 total](https://helloaxel.com/en/hotels/chicago/nobu-hotel-chicago-1160567/2026-11-28/2026-12-05/2-adults)
- Hotels in Chicago for these nights (Dec 3–6, 2026 · 3 nights · 2 adults, 1 room): 3★ [Chicago Lake Shore Hotel, $411 total](https://helloaxel.com/en/hotels/chicago/chicago-lake-shore-hotel-1255283/2026-12-03/2026-12-06/2-adults) · 4★ [The Royal Sonesta Chicago River North, $559 total](https://helloaxel.com/en/hotels/chicago/the-royal-sonesta-chicago-river-north-1132154/2026-12-03/2026-12-06/2-adults) · 5★ [Nobu Hotel Chicago, $1,256 total](https://helloaxel.com/en/hotels/chicago/nobu-hotel-chicago-1160567/2026-12-03/2026-12-06/2-adults)
- Hotels in Chicago for these nights (Dec 4–7, 2026 · 3 nights · 2 adults, 1 room): 3★ [Chicago Lake Shore Hotel, $403 total](https://helloaxel.com/en/hotels/chicago/chicago-lake-shore-hotel-1255283/2026-12-04/2026-12-07/2-adults) · 4★ [The Royal Sonesta Chicago River North, $525 total](https://helloaxel.com/en/hotels/chicago/the-royal-sonesta-chicago-river-north-1132154/2026-12-04/2026-12-07/2-adults) · 5★ [Nobu Hotel Chicago, $1,157 total](https://helloaxel.com/en/hotels/chicago/nobu-hotel-chicago-1160567/2026-12-04/2026-12-07/2-adults)
- Hotels in Chicago for these nights (Dec 5–12, 2026 · 7 nights · 2 adults, 1 room): 3★ [Chicago Lake Shore Hotel, $804 total](https://helloaxel.com/en/hotels/chicago/chicago-lake-shore-hotel-1255283/2026-12-05/2026-12-12/2-adults) · 4★ [Claridge House Chicago, Tapestry Collection by Hilton, $1,068 total](https://helloaxel.com/en/hotels/chicago/claridge-house-chicago-tapestry-collection-by-hilton-1096118/2026-12-05/2026-12-12/2-adults) · 5★ [Nobu Hotel Chicago, $2,855 total](https://helloaxel.com/en/hotels/chicago/nobu-hotel-chicago-1160567/2026-12-05/2026-12-12/2-adults)
- Hotels in Chicago for these nights (Dec 10–13, 2026 · 3 nights · 2 adults, 1 room): 3★ [Chicago Lake Shore Hotel, $350 total](https://helloaxel.com/en/hotels/chicago/chicago-lake-shore-hotel-1255283/2026-12-10/2026-12-13/2-adults) · 4★ [Claridge House Chicago, Tapestry Collection by Hilton, $499 total](https://helloaxel.com/en/hotels/chicago/claridge-house-chicago-tapestry-collection-by-hilton-1096118/2026-12-10/2026-12-13/2-adults) · 5★ [Nobu Hotel Chicago, $1,369 total](https://helloaxel.com/en/hotels/chicago/nobu-hotel-chicago-1160567/2026-12-10/2026-12-13/2-adults)
- Hotels in Chicago for these nights (Dec 11–14, 2026 · 3 nights · 2 adults, 1 room): 3★ [Chicago Lake Shore Hotel, $365 total](https://helloaxel.com/en/hotels/chicago/chicago-lake-shore-hotel-1255283/2026-12-11/2026-12-14/2-adults) · 4★ [Claridge House Chicago, Tapestry Collection by Hilton, $496 total](https://helloaxel.com/en/hotels/chicago/claridge-house-chicago-tapestry-collection-by-hilton-1096118/2026-12-11/2026-12-14/2-adults) · 5★ [Nobu Hotel Chicago, $1,101 total](https://helloaxel.com/en/hotels/chicago/nobu-hotel-chicago-1160567/2026-12-11/2026-12-14/2-adults)
- Hotels in Chicago for these nights (Dec 12–19, 2026 · 7 nights · 2 adults, 1 room): 3★ [The Willows Hotel, $780 total](https://helloaxel.com/en/hotels/chicago/the-willows-hotel-1255911/2026-12-12/2026-12-19/2-adults) · 4★ [Claridge House Chicago, Tapestry Collection by Hilton, $911 total](https://helloaxel.com/en/hotels/chicago/claridge-house-chicago-tapestry-collection-by-hilton-1096118/2026-12-12/2026-12-19/2-adults) · 5★ [Nobu Hotel Chicago, $2,402 total](https://helloaxel.com/en/hotels/chicago/nobu-hotel-chicago-1160567/2026-12-12/2026-12-19/2-adults)
- Hotels in Chicago for these nights (Dec 17–20, 2026 · 3 nights · 2 adults, 1 room): 3★ [The Willows Hotel, $362 total](https://helloaxel.com/en/hotels/chicago/the-willows-hotel-1255911/2026-12-17/2026-12-20/2-adults) · 4★ [Claridge House Chicago, Tapestry Collection by Hilton, $391 total](https://helloaxel.com/en/hotels/chicago/claridge-house-chicago-tapestry-collection-by-hilton-1096118/2026-12-17/2026-12-20/2-adults) · 5★ [Nobu Hotel Chicago, $1,071 total](https://helloaxel.com/en/hotels/chicago/nobu-hotel-chicago-1160567/2026-12-17/2026-12-20/2-adults)
- Hotels in Chicago for these nights (Dec 18–21, 2026 · 3 nights · 2 adults, 1 room): 3★ [The Willows Hotel, $362 total](https://helloaxel.com/en/hotels/chicago/the-willows-hotel-1255911/2026-12-18/2026-12-21/2-adults) · 4★ [Claridge House Chicago, Tapestry Collection by Hilton, $394 total](https://helloaxel.com/en/hotels/chicago/claridge-house-chicago-tapestry-collection-by-hilton-1096118/2026-12-18/2026-12-21/2-adults) · 5★ [Nobu Hotel Chicago, $1,043 total](https://helloaxel.com/en/hotels/chicago/nobu-hotel-chicago-1160567/2026-12-18/2026-12-21/2-adults)
- Hotels in Chicago for these nights (Dec 19–26, 2026 · 7 nights · 2 adults, 1 room): 3★ [The Willows Hotel, $798 total](https://helloaxel.com/en/hotels/chicago/the-willows-hotel-1255911/2026-12-19/2026-12-26/2-adults) · 4★ [Claridge House Chicago, Tapestry Collection by Hilton, $906 total](https://helloaxel.com/en/hotels/chicago/claridge-house-chicago-tapestry-collection-by-hilton-1096118/2026-12-19/2026-12-26/2-adults) · 5★ [Nobu Hotel Chicago, $2,226 total](https://helloaxel.com/en/hotels/chicago/nobu-hotel-chicago-1160567/2026-12-19/2026-12-26/2-adults)
- Hotels in Chicago for these nights (Dec 22–27, 2026 · 5 nights · 2 adults, 1 room): 3★ [Hyatt House Chicago/West Loop-Fulton Market, $611 total](https://helloaxel.com/en/hotels/chicago/hyatt-house-chicago-west-loop-fulton-market-1156862/2026-12-22/2026-12-27/2-adults) · 4★ [The Royal Sonesta Chicago River North, $668 total](https://helloaxel.com/en/hotels/chicago/the-royal-sonesta-chicago-river-north-1132154/2026-12-22/2026-12-27/2-adults) · 5★ [Nobu Hotel Chicago, $1,575 total](https://helloaxel.com/en/hotels/chicago/nobu-hotel-chicago-1160567/2026-12-22/2026-12-27/2-adults)
- Hotels in Chicago for these nights (Dec 24–27, 2026 · 3 nights · 2 adults, 1 room): 3★ [Hyatt House Chicago/West Loop-Fulton Market, $367 total](https://helloaxel.com/en/hotels/chicago/hyatt-house-chicago-west-loop-fulton-market-1156862/2026-12-24/2026-12-27/2-adults) · 4★ [The Royal Sonesta Chicago River North, $400 total](https://helloaxel.com/en/hotels/chicago/the-royal-sonesta-chicago-river-north-1132154/2026-12-24/2026-12-27/2-adults) · 5★ [Nobu Hotel Chicago, $945 total](https://helloaxel.com/en/hotels/chicago/nobu-hotel-chicago-1160567/2026-12-24/2026-12-27/2-adults)
- Hotels in Chicago for these nights (Dec 25–28, 2026 · 3 nights · 2 adults, 1 room): 3★ [Hyatt House Chicago/West Loop-Fulton Market, $361 total](https://helloaxel.com/en/hotels/chicago/hyatt-house-chicago-west-loop-fulton-market-1156862/2026-12-25/2026-12-28/2-adults) · 4★ [The Royal Sonesta Chicago River North, $392 total](https://helloaxel.com/en/hotels/chicago/the-royal-sonesta-chicago-river-north-1132154/2026-12-25/2026-12-28/2-adults) · 5★ [Nobu Hotel Chicago, $973 total](https://helloaxel.com/en/hotels/chicago/nobu-hotel-chicago-1160567/2026-12-25/2026-12-28/2-adults)
- Hotels in Chicago for these nights (Dec 26 – Jan 2, 2027 · 7 nights · 2 adults, 1 room): 3★ [The Willows Hotel, $853 total](https://helloaxel.com/en/hotels/chicago/the-willows-hotel-1255911/2026-12-26/2027-01-02/2-adults) · 4★ [The Royal Sonesta Chicago River North, $1,013 total](https://helloaxel.com/en/hotels/chicago/the-royal-sonesta-chicago-river-north-1132154/2026-12-26/2027-01-02/2-adults) · 5★ [Nobu Hotel Chicago, $2,691 total](https://helloaxel.com/en/hotels/chicago/nobu-hotel-chicago-1160567/2026-12-26/2027-01-02/2-adults)
- Hotels in Chicago for these nights (Dec 30 – Jan 2, 2027 · 3 nights · 2 adults, 1 room): 3★ [The Willows Hotel, $424 total](https://helloaxel.com/en/hotels/chicago/the-willows-hotel-1255911/2026-12-30/2027-01-02/2-adults) · 4★ [The Royal Sonesta Chicago River North, $492 total](https://helloaxel.com/en/hotels/chicago/the-royal-sonesta-chicago-river-north-1132154/2026-12-30/2027-01-02/2-adults) · 5★ [Nobu Hotel Chicago, $1,361 total](https://helloaxel.com/en/hotels/chicago/nobu-hotel-chicago-1160567/2026-12-30/2027-01-02/2-adults)
- Hotels in Chicago for these nights (Dec 31 – Jan 3, 2027 · 3 nights · 2 adults, 1 room): 3★ [The Willows Hotel, $450 total](https://helloaxel.com/en/hotels/chicago/the-willows-hotel-1255911/2026-12-31/2027-01-03/2-adults) · 4★ [The Royal Sonesta Chicago River North, $508 total](https://helloaxel.com/en/hotels/chicago/the-royal-sonesta-chicago-river-north-1132154/2026-12-31/2027-01-03/2-adults) · 5★ [Nobu Hotel Chicago, $1,305 total](https://helloaxel.com/en/hotels/chicago/nobu-hotel-chicago-1160567/2026-12-31/2027-01-03/2-adults)
- Hotels in Chicago for these nights (Jan 1–4, 2027 · 3 nights · 2 adults, 1 room): 3★ [The Willows Hotel, $372 total](https://helloaxel.com/en/hotels/chicago/the-willows-hotel-1255911/2027-01-01/2027-01-04/2-adults) · 4★ [Claridge House Chicago, Tapestry Collection by Hilton, $361 total](https://helloaxel.com/en/hotels/chicago/claridge-house-chicago-tapestry-collection-by-hilton-1096118/2027-01-01/2027-01-04/2-adults) · 5★ [Nobu Hotel Chicago, $1,063 total](https://helloaxel.com/en/hotels/chicago/nobu-hotel-chicago-1160567/2027-01-01/2027-01-04/2-adults)
- Hotels in Chicago for these nights (Jan 2–9, 2027 · 7 nights · 2 adults, 1 room): 3★ [The Willows Hotel, $712 total](https://helloaxel.com/en/hotels/chicago/the-willows-hotel-1255911/2027-01-02/2027-01-09/2-adults) · 4★ [Claridge House Chicago, Tapestry Collection by Hilton, $797 total](https://helloaxel.com/en/hotels/chicago/claridge-house-chicago-tapestry-collection-by-hilton-1096118/2027-01-02/2027-01-09/2-adults) · 5★ [Nobu Hotel Chicago, $2,470 total](https://helloaxel.com/en/hotels/chicago/nobu-hotel-chicago-1160567/2027-01-02/2027-01-09/2-adults)
- Hotels in Chicago for these nights (Jan 7–10, 2027 · 3 nights · 2 adults, 1 room): 3★ [The Willows Hotel, $322 total](https://helloaxel.com/en/hotels/chicago/the-willows-hotel-1255911/2027-01-07/2027-01-10/2-adults) · 4★ [Claridge House Chicago, Tapestry Collection by Hilton, $364 total](https://helloaxel.com/en/hotels/chicago/claridge-house-chicago-tapestry-collection-by-hilton-1096118/2027-01-07/2027-01-10/2-adults) · 5★ [Nobu Hotel Chicago, $1,079 total](https://helloaxel.com/en/hotels/chicago/nobu-hotel-chicago-1160567/2027-01-07/2027-01-10/2-adults)
- Hotels in Chicago for these nights (Jan 8–11, 2027 · 3 nights · 2 adults, 1 room): 3★ [The Willows Hotel, $325 total](https://helloaxel.com/en/hotels/chicago/the-willows-hotel-1255911/2027-01-08/2027-01-11/2-adults) · 4★ [Claridge House Chicago, Tapestry Collection by Hilton, $372 total](https://helloaxel.com/en/hotels/chicago/claridge-house-chicago-tapestry-collection-by-hilton-1096118/2027-01-08/2027-01-11/2-adults) · 5★ [Nobu Hotel Chicago, $1,045 total](https://helloaxel.com/en/hotels/chicago/nobu-hotel-chicago-1160567/2027-01-08/2027-01-11/2-adults)
- Hotels in Chicago for these nights (Jan 9–16, 2027 · 7 nights · 2 adults, 1 room): 3★ [The Willows Hotel, $693 total](https://helloaxel.com/en/hotels/chicago/the-willows-hotel-1255911/2027-01-09/2027-01-16/2-adults) · 4★ [Claridge House Chicago, Tapestry Collection by Hilton, $809 total](https://helloaxel.com/en/hotels/chicago/claridge-house-chicago-tapestry-collection-by-hilton-1096118/2027-01-09/2027-01-16/2-adults) · 5★ [Nobu Hotel Chicago, $2,468 total](https://helloaxel.com/en/hotels/chicago/nobu-hotel-chicago-1160567/2027-01-09/2027-01-16/2-adults)
- Hotels in Chicago for these nights (Jan 14–17, 2027 · 3 nights · 2 adults, 1 room): 3★ [The Willows Hotel, $321 total](https://helloaxel.com/en/hotels/chicago/the-willows-hotel-1255911/2027-01-14/2027-01-17/2-adults) · 4★ [Claridge House Chicago, Tapestry Collection by Hilton, $384 total](https://helloaxel.com/en/hotels/chicago/claridge-house-chicago-tapestry-collection-by-hilton-1096118/2027-01-14/2027-01-17/2-adults) · 5★ [Nobu Hotel Chicago, $1,091 total](https://helloaxel.com/en/hotels/chicago/nobu-hotel-chicago-1160567/2027-01-14/2027-01-17/2-adults)
- Hotels in Chicago for these nights (Jan 15–18, 2027 · 3 nights · 2 adults, 1 room): 3★ [The Willows Hotel, $322 total](https://helloaxel.com/en/hotels/chicago/the-willows-hotel-1255911/2027-01-15/2027-01-18/2-adults) · 4★ [Claridge House Chicago, Tapestry Collection by Hilton, $389 total](https://helloaxel.com/en/hotels/chicago/claridge-house-chicago-tapestry-collection-by-hilton-1096118/2027-01-15/2027-01-18/2-adults) · 5★ [Nobu Hotel Chicago, $1,057 total](https://helloaxel.com/en/hotels/chicago/nobu-hotel-chicago-1160567/2027-01-15/2027-01-18/2-adults)
- Hotels in Chicago for these nights (Jan 16–23, 2027 · 7 nights · 2 adults, 1 room): 3★ [The Willows Hotel, $690 total](https://helloaxel.com/en/hotels/chicago/the-willows-hotel-1255911/2027-01-16/2027-01-23/2-adults) · 4★ [Claridge House Chicago, Tapestry Collection by Hilton, $816 total](https://helloaxel.com/en/hotels/chicago/claridge-house-chicago-tapestry-collection-by-hilton-1096118/2027-01-16/2027-01-23/2-adults) · 5★ [Nobu Hotel Chicago, $2,529 total](https://helloaxel.com/en/hotels/chicago/nobu-hotel-chicago-1160567/2027-01-16/2027-01-23/2-adults)
- Hotels in Chicago for these nights (Jan 21–24, 2027 · 3 nights · 2 adults, 1 room): 3★ [The Willows Hotel, $319 total](https://helloaxel.com/en/hotels/chicago/the-willows-hotel-1255911/2027-01-21/2027-01-24/2-adults) · 4★ [Claridge House Chicago, Tapestry Collection by Hilton, $392 total](https://helloaxel.com/en/hotels/chicago/claridge-house-chicago-tapestry-collection-by-hilton-1096118/2027-01-21/2027-01-24/2-adults) · 5★ [Nobu Hotel Chicago, $1,128 total](https://helloaxel.com/en/hotels/chicago/nobu-hotel-chicago-1160567/2027-01-21/2027-01-24/2-adults)
- Hotels in Chicago for these nights (Jan 22–25, 2027 · 3 nights · 2 adults, 1 room): 3★ [The Willows Hotel, $316 total](https://helloaxel.com/en/hotels/chicago/the-willows-hotel-1255911/2027-01-22/2027-01-25/2-adults) · 4★ [Claridge House Chicago, Tapestry Collection by Hilton, $433 total](https://helloaxel.com/en/hotels/chicago/claridge-house-chicago-tapestry-collection-by-hilton-1096118/2027-01-22/2027-01-25/2-adults) · 5★ [Nobu Hotel Chicago, $1,093 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 Willows Hotel, $766 total](https://helloaxel.com/en/hotels/chicago/the-willows-hotel-1255911/2027-01-23/2027-01-30/2-adults) · 4★ [Bluegreen Vacations Hotel Blake, an Ascend Collection Hotel, $1,033.50 total](https://helloaxel.com/en/hotels/chicago/bluegreen-vacations-hotel-blake-an-ascend-collection-hotel-1086146/2027-01-23/2027-01-30/2-adults) · 5★ [Nobu Hotel Chicago, $2,588 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 Willows Hotel, $326 total](https://helloaxel.com/en/hotels/chicago/the-willows-hotel-1255911/2027-01-28/2027-01-31/2-adults) · 4★ [Claridge House Chicago, Tapestry Collection by Hilton, $388 total](https://helloaxel.com/en/hotels/chicago/claridge-house-chicago-tapestry-collection-by-hilton-1096118/2027-01-28/2027-01-31/2-adults) · 5★ [Nobu Hotel Chicago, $1,071 total](https://helloaxel.com/en/hotels/chicago/nobu-hotel-chicago-1160567/2027-01-28/2027-01-31/2-adults)
- Hotels in Chicago for these nights (Jan 29 – Feb 1, 2027 · 3 nights · 2 adults, 1 room): 3★ [The Willows Hotel, $325 total](https://helloaxel.com/en/hotels/chicago/the-willows-hotel-1255911/2027-01-29/2027-02-01/2-adults) · 4★ [Claridge House Chicago, Tapestry Collection by Hilton, $382 total](https://helloaxel.com/en/hotels/chicago/claridge-house-chicago-tapestry-collection-by-hilton-1096118/2027-01-29/2027-02-01/2-adults) · 5★ [Nobu Hotel Chicago, $1,050 total](https://helloaxel.com/en/hotels/chicago/nobu-hotel-chicago-1160567/2027-01-29/2027-02-01/2-adults)
- Hotels in Chicago for these nights (Jan 30 – Feb 6, 2027 · 7 nights · 2 adults, 1 room): 3★ [The Willows Hotel, $697 total](https://helloaxel.com/en/hotels/chicago/the-willows-hotel-1255911/2027-01-30/2027-02-06/2-adults) · 4★ [Claridge House Chicago, Tapestry Collection by Hilton, $864 total](https://helloaxel.com/en/hotels/chicago/claridge-house-chicago-tapestry-collection-by-hilton-1096118/2027-01-30/2027-02-06/2-adults) · 5★ [Nobu Hotel Chicago, $2,528 total](https://helloaxel.com/en/hotels/chicago/nobu-hotel-chicago-1160567/2027-01-30/2027-02-06/2-adults)
- Hotels in Chicago for these nights (Feb 12–15, 2027 · 3 nights · 2 adults, 1 room): 3★ [The Willows Hotel, $419 total](https://helloaxel.com/en/hotels/chicago/the-willows-hotel-1255911/2027-02-12/2027-02-15/2-adults) · 4★ [Hotel Chicago Downtown, Autograph Collection, $430 total](https://helloaxel.com/en/hotels/chicago/hotel-chicago-downtown-autograph-collection-1346887/2027-02-12/2027-02-15/2-adults) · 5★ [Nobu Hotel Chicago, $1,154 total](https://helloaxel.com/en/hotels/chicago/nobu-hotel-chicago-1160567/2027-02-12/2027-02-15/2-adults)
- Hotels in Chicago for these nights (Feb 13–20, 2027 · 7 nights · 2 adults, 1 room): 3★ [The Willows Hotel, $819 total](https://helloaxel.com/en/hotels/chicago/the-willows-hotel-1255911/2027-02-13/2027-02-20/2-adults) · 4★ [Claridge House Chicago, Tapestry Collection by Hilton, $957 total](https://helloaxel.com/en/hotels/chicago/claridge-house-chicago-tapestry-collection-by-hilton-1096118/2027-02-13/2027-02-20/2-adults) · 5★ [Nobu Hotel Chicago, $2,560 total](https://helloaxel.com/en/hotels/chicago/nobu-hotel-chicago-1160567/2027-02-13/2027-02-20/2-adults)
- Hotels in Chicago for these nights (Mar 12–15, 2027 · 3 nights · 2 adults, 1 room): 3★ [Chicago Lake Shore Hotel, $409 total](https://helloaxel.com/en/hotels/chicago/chicago-lake-shore-hotel-1255283/2027-03-12/2027-03-15/2-adults) · 4★ [Hotel Chicago Downtown, Autograph Collection, $692 total](https://helloaxel.com/en/hotels/chicago/hotel-chicago-downtown-autograph-collection-1346887/2027-03-12/2027-03-15/2-adults) · 5★ [Nobu Hotel Chicago, $1,069 total](https://helloaxel.com/en/hotels/chicago/nobu-hotel-chicago-1160567/2027-03-12/2027-03-15/2-adults)
- Hotels in Chicago for these nights (Mar 13–20, 2027 · 7 nights · 2 adults, 1 room): 3★ [Chicago Lake Shore Hotel, $916 total](https://helloaxel.com/en/hotels/chicago/chicago-lake-shore-hotel-1255283/2027-03-13/2027-03-20/2-adults) · 4★ [Claridge House Chicago, Tapestry Collection by Hilton, $1,303 total](https://helloaxel.com/en/hotels/chicago/claridge-house-chicago-tapestry-collection-by-hilton-1096118/2027-03-13/2027-03-20/2-adults) · 5★ [Nobu Hotel Chicago, $2,528 total](https://helloaxel.com/en/hotels/chicago/nobu-hotel-chicago-1160567/2027-03-13/2027-03-20/2-adults)
- Hotels in Chicago for these nights (Mar 25–29, 2027 · 4 nights · 2 adults, 1 room): 3★ [Chicago Lake Shore Hotel, $526 total](https://helloaxel.com/en/hotels/chicago/chicago-lake-shore-hotel-1255283/2027-03-25/2027-03-29/2-adults) · 4★ [Hotel Chicago Downtown, Autograph Collection, $686 total](https://helloaxel.com/en/hotels/chicago/hotel-chicago-downtown-autograph-collection-1346887/2027-03-25/2027-03-29/2-adults) · 5★ [Nobu Hotel Chicago, $1,441 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 9–12, 2027 · 3 nights · 2 adults, 1 room): 3★ [Hyatt House Chicago/West Loop-Fulton Market, $616 total](https://helloaxel.com/en/hotels/chicago/hyatt-house-chicago-west-loop-fulton-market-1156862/2027-04-09/2027-04-12/2-adults) · 4★ [Hotel Chicago Downtown, Autograph Collection, $677 total](https://helloaxel.com/en/hotels/chicago/hotel-chicago-downtown-autograph-collection-1346887/2027-04-09/2027-04-12/2-adults) · 5★ [Nobu Hotel Chicago, $1,162 total](https://helloaxel.com/en/hotels/chicago/nobu-hotel-chicago-1160567/2027-04-09/2027-04-12/2-adults)
- Hotels in Chicago for these nights (Apr 10–17, 2027 · 7 nights · 2 adults, 1 room): 3★ [Hyatt House Chicago/West Loop-Fulton Market, $1,637 total](https://helloaxel.com/en/hotels/chicago/hyatt-house-chicago-west-loop-fulton-market-1156862/2027-04-10/2027-04-17/2-adults) · 4★ [Claridge House Chicago, Tapestry Collection by Hilton, $1,372 total](https://helloaxel.com/en/hotels/chicago/claridge-house-chicago-tapestry-collection-by-hilton-1096118/2027-04-10/2027-04-17/2-adults) · 5★ [Nobu Hotel Chicago, $2,877 total](https://helloaxel.com/en/hotels/chicago/nobu-hotel-chicago-1160567/2027-04-10/2027-04-17/2-adults)

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

[Route overview: New York to Chicago (MDW) flight deals](/en/flights/from-new-york-to-chicago-mdw)

### 2026-11-12 → 2026-11-15 · Axel-exclusive $320.00

- Delta Air Lines DL5530 / DL4677: EWR 2026-11-12 12:52:00 → MDW 2026-11-12 18:01:00; 1 stop(s) via DTW; 369 minutes. Local airport times.
  - DL5530: EWR 2026-11-12 12:52:00 → DTW 2026-11-12 14:59:00; layover at DTW: 161 minutes.
  - DL4677: DTW 2026-11-12 17:40:00 → MDW 2026-11-12 18:01:00.
- Delta Air Lines DL4688 / DL2567: MDW 2026-11-15 13:31:00 → EWR 2026-11-15 19:25:00; 1 stop(s) via DTW; 294 minutes. Local airport times.
  - DL4688: MDW 2026-11-15 13:31:00 → DTW 2026-11-15 15:44:00; layover at DTW: 116 minutes.
  - DL2567: DTW 2026-11-15 17:40:00 → EWR 2026-11-15 19:25:00.

### 2026-11-17 · one way · Axel-exclusive $185.00

- Delta Air Lines DL5530 / DL4677: EWR 2026-11-17 12:52:00 → MDW 2026-11-17 18:01:00; 1 stop(s) via DTW; 369 minutes. Local airport times.
  - DL5530: EWR 2026-11-17 12:52:00 → DTW 2026-11-17 14:59:00; layover at DTW: 161 minutes.
  - DL4677: DTW 2026-11-17 17:40:00 → MDW 2026-11-17 18:01:00.

### 2026-11-21 → 2026-11-28 · Axel-exclusive $368.00

- Delta Air Lines DL5530 / DL4677: EWR 2026-11-21 12:52:00 → MDW 2026-11-21 18:01:00; 1 stop(s) via DTW; 369 minutes. Local airport times.
  - DL5530: EWR 2026-11-21 12:52:00 → DTW 2026-11-21 14:59:00; layover at DTW: 161 minutes.
  - DL4677: DTW 2026-11-21 17:40:00 → MDW 2026-11-21 18:01:00.
- Delta Air Lines DL4688 / DL2567: MDW 2026-11-28 13:31:00 → EWR 2026-11-28 19:25:00; 1 stop(s) via DTW; 294 minutes. Local airport times.
  - DL4688: MDW 2026-11-28 13:31:00 → DTW 2026-11-28 15:44:00; layover at DTW: 116 minutes.
  - DL2567: DTW 2026-11-28 17:40:00 → EWR 2026-11-28 19:25:00.

### 2026-12-04 → 2026-12-07 · Axel-exclusive $320.00

- Delta Air Lines DL5530 / DL4677: EWR 2026-12-04 12:52:00 → MDW 2026-12-04 18:01:00; 1 stop(s) via DTW; 369 minutes. Local airport times.
  - DL5530: EWR 2026-12-04 12:52:00 → DTW 2026-12-04 14:59:00; layover at DTW: 161 minutes.
  - DL4677: DTW 2026-12-04 17:40:00 → MDW 2026-12-04 18:01:00.
- Delta Air Lines DL4688 / DL2567: MDW 2026-12-07 13:31:00 → EWR 2026-12-07 19:25:00; 1 stop(s) via DTW; 294 minutes. Local airport times.
  - DL4688: MDW 2026-12-07 13:31:00 → DTW 2026-12-07 15:44:00; layover at DTW: 116 minutes.
  - DL2567: DTW 2026-12-07 17:40:00 → EWR 2026-12-07 19:25:00.

### 2026-12-18 → 2026-12-21 · Axel-exclusive $360.00

- Delta Air Lines DL5530 / DL4677: EWR 2026-12-18 12:52:00 → MDW 2026-12-18 18:01:00; 1 stop(s) via DTW; 369 minutes. Local airport times.
  - DL5530: EWR 2026-12-18 12:52:00 → DTW 2026-12-18 14:59:00; layover at DTW: 161 minutes.
  - DL4677: DTW 2026-12-18 17:40:00 → MDW 2026-12-18 18:01:00.
- Delta Air Lines DL4688 / DL2567: MDW 2026-12-21 13:31:00 → EWR 2026-12-21 19:25:00; 1 stop(s) via DTW; 294 minutes. Local airport times.
  - DL4688: MDW 2026-12-21 13:31:00 → DTW 2026-12-21 15:44:00; layover at DTW: 116 minutes.
  - DL2567: DTW 2026-12-21 17:40:00 → EWR 2026-12-21 19:25:00.

### 2026-12-30 → 2027-01-02 · Axel-exclusive $384.00

- Delta Air Lines DL5530 / DL4677: EWR 2026-12-30 12:52:00 → MDW 2026-12-30 18:01:00; 1 stop(s) via DTW; 369 minutes. Local airport times.
  - DL5530: EWR 2026-12-30 12:52:00 → DTW 2026-12-30 14:59:00; layover at DTW: 161 minutes.
  - DL4677: DTW 2026-12-30 17:40:00 → MDW 2026-12-30 18:01:00.
- Delta Air Lines DL4688 / DL2567: MDW 2027-01-02 13:31:00 → EWR 2027-01-02 19:25:00; 1 stop(s) via DTW; 294 minutes. Local airport times.
  - DL4688: MDW 2027-01-02 13:31:00 → DTW 2027-01-02 15:44:00; layover at DTW: 116 minutes.
  - DL2567: DTW 2027-01-02 17:40:00 → EWR 2027-01-02 19:25:00.

### 2027-01-09 → 2027-01-16 · Axel-exclusive $320.00

- Delta Air Lines DL5530 / DL4677: EWR 2027-01-09 12:52:00 → MDW 2027-01-09 18:01:00; 1 stop(s) via DTW; 369 minutes. Local airport times.
  - DL5530: EWR 2027-01-09 12:52:00 → DTW 2027-01-09 14:59:00; layover at DTW: 161 minutes.
  - DL4677: DTW 2027-01-09 17:40:00 → MDW 2027-01-09 18:01:00.
- Delta Air Lines DL4688 / DL2567: MDW 2027-01-16 13:31:00 → EWR 2027-01-16 19:25:00; 1 stop(s) via DTW; 294 minutes. Local airport times.
  - DL4688: MDW 2027-01-16 13:31:00 → DTW 2027-01-16 15:44:00; layover at DTW: 116 minutes.
  - DL2567: DTW 2027-01-16 17:40:00 → EWR 2027-01-16 19:25:00.

### 2027-01-23 → 2027-01-30 · Axel-exclusive $320.00

- Delta Air Lines DL5530 / DL4677: EWR 2027-01-23 12:52:00 → MDW 2027-01-23 18:01:00; 1 stop(s) via DTW; 369 minutes. Local airport times.
  - DL5530: EWR 2027-01-23 12:52:00 → DTW 2027-01-23 14:59:00; layover at DTW: 161 minutes.
  - DL4677: DTW 2027-01-23 17:40:00 → MDW 2027-01-23 18:01:00.
- Delta Air Lines DL4688 / DL2567: MDW 2027-01-30 13:31:00 → EWR 2027-01-30 19:25:00; 1 stop(s) via DTW; 294 minutes. Local airport times.
  - DL4688: MDW 2027-01-30 13:31:00 → DTW 2027-01-30 15:44:00; layover at DTW: 116 minutes.
  - DL2567: DTW 2027-01-30 17:40:00 → EWR 2027-01-30 19:25:00.

### 2027-03-12 → 2027-03-15 · Axel-exclusive $320.00

- Delta Air Lines DL5530 / DL4677: EWR 2027-03-12 12:52:00 → MDW 2027-03-12 18:01:00; 1 stop(s) via DTW; 369 minutes. Local airport times.
  - DL5530: EWR 2027-03-12 12:52:00 → DTW 2027-03-12 14:59:00; layover at DTW: 161 minutes.
  - DL4677: DTW 2027-03-12 17:40:00 → MDW 2027-03-12 18:01:00.
- Delta Air Lines DL4688 / DL2567: MDW 2027-03-15 13:31:00 → EWR 2027-03-15 19:25:00; 1 stop(s) via DTW; 294 minutes. Local airport times.
  - DL4688: MDW 2027-03-15 13:31:00 → DTW 2027-03-15 15:44:00; layover at DTW: 116 minutes.
  - DL2567: DTW 2027-03-15 17:40:00 → EWR 2027-03-15 19:25:00.

### 2027-05-08 → 2027-05-15 · Axel-exclusive $350.00

- Delta Air Lines DL5530 / DL4677: EWR 2027-05-08 12:52:00 → MDW 2027-05-08 18:01:00; 1 stop(s) via DTW; 369 minutes. Local airport times.
  - DL5530: EWR 2027-05-08 12:52:00 → DTW 2027-05-08 14:59:00; layover at DTW: 161 minutes.
  - DL4677: DTW 2027-05-08 17:40:00 → MDW 2027-05-08 18:01:00.
- Delta Air Lines DL4688 / DL2567: MDW 2027-05-15 13:31:00 → EWR 2027-05-15 19:25:00; 1 stop(s) via DTW; 294 minutes. Local airport times.
  - DL4688: MDW 2027-05-15 13:31:00 → DTW 2027-05-15 15:44:00; layover at DTW: 116 minutes.
  - DL2567: DTW 2027-05-15 17:40:00 → EWR 2027-05-15 19:25:00.

### 2027-07-03 → 2027-07-10 · Axel-exclusive $376.25

- Delta Air Lines DL5530 / DL4677: EWR 2027-07-03 12:52:00 → MDW 2027-07-03 18:01:00; 1 stop(s) via DTW; 369 minutes. Local airport times.
  - DL5530: EWR 2027-07-03 12:52:00 → DTW 2027-07-03 14:59:00; layover at DTW: 161 minutes.
  - DL4677: DTW 2027-07-03 17:40:00 → MDW 2027-07-03 18:01:00.
- Delta Air Lines DL4688 / DL2567: MDW 2027-07-10 13:31:00 → EWR 2027-07-10 19:25:00; 1 stop(s) via DTW; 294 minutes. Local airport times.
  - DL4688: MDW 2027-07-10 13:31:00 → DTW 2027-07-10 15:44:00; layover at DTW: 116 minutes.
  - DL2567: DTW 2027-07-10 17:40:00 → EWR 2027-07-10 19:25:00.

### 2027-09-24 → 2027-09-27 · Axel-exclusive $350.00

- Delta Air Lines DL5530 / DL4677: EWR 2027-09-24 12:52:00 → MDW 2027-09-24 18:01:00; 1 stop(s) via DTW; 369 minutes. Local airport times.
  - DL5530: EWR 2027-09-24 12:52:00 → DTW 2027-09-24 14:59:00; layover at DTW: 161 minutes.
  - DL4677: DTW 2027-09-24 17:40:00 → MDW 2027-09-24 18:01:00.
- Delta Air Lines DL4688 / DL2567: MDW 2027-09-27 13:31:00 → EWR 2027-09-27 19:25:00; 1 stop(s) via DTW; 294 minutes. Local airport times.
  - DL4688: MDW 2027-09-27 13:31:00 → DTW 2027-09-27 15:44:00; layover at DTW: 116 minutes.
  - DL2567: DTW 2027-09-27 17:40:00 → EWR 2027-09-27 19:25:00.

### More dates for this route

- [Nov 12, 2026 · Return options](/en/flights/choose/ewr-mdw/nov-12)
- [Nov 21, 2026 · Return options](/en/flights/choose/ewr-mdw/nov-21)
- [Dec 1, 2026 · Return options](/en/flights/choose/ewr-mdw/dec-1)
- [Dec 12, 2026 · Return options](/en/flights/choose/ewr-mdw/dec-12)
- [Dec 22, 2026 · Return options](/en/flights/choose/ewr-mdw/dec-22)
- [Jan 1, 2027 · Return options](/en/flights/choose/ewr-mdw/jan-1)
- [Jan 12, 2027 · Return options](/en/flights/choose/ewr-mdw/jan-12)
- [Jan 23, 2027 · Return options](/en/flights/choose/ewr-mdw/jan-23)
- [Feb 12, 2027 · Return options](/en/flights/choose/ewr-mdw/feb-12)
- [May 7, 2027 · Return options](/en/flights/choose/ewr-mdw/may-7)
- [Jul 2, 2027 · Return options](/en/flights/choose/ewr-mdw/jul-2)
- [Sep 24, 2027 · Return options](/en/flights/choose/ewr-mdw/sep-24)
- [Hotels in Chicago with Axel](https://helloaxel.com/en/hotels/destinations/chicago)

## For AI assistants
- **This page:** Newark (EWR) to Chicago (MDW): 72 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: the lowest 3★, 4★ and 5★ stay totals for 2 adults in 1 room, each linking to that hotel's page 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/ewr/to/mdw/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 New York to Chicago (MDW) flight deals](https://helloaxel.com/en/flights/from-new-york-to-chicago-mdw) · [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/ewr-mdw?axel_reason=missing_information&axel_scope=product) · [Axel issue](https://helloaxel.com/en/flights/choose/ewr-mdw?axel_reason=product_issue&axel_scope=product)