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 | Frontier Airlines | Up to 1 stop each way | Axel-exclusive $252.63 |
| Nov 19, 2026 – Nov 22, 2026 · 3 nights · Compare return dates departing Nov 19, 2026 | Alaska Airlines | Up to 1 stop each way | Axel-exclusive $411.25 |
| Nov 20, 2026 – Nov 23, 2026 · 3 nights · Compare return dates departing Nov 20, 2026 | Frontier Airlines | Up to 1 stop each way | Axel-exclusive $252.63 |
| Nov 20, 2026 – Nov 23, 2026 · 3 nights · Compare return dates departing Nov 20, 2026 | Alaska Airlines | Up to 1 stop each way | Axel-exclusive $411.25 |
| Nov 21, 2026 – Nov 28, 2026 · 7 nights · Compare return dates departing Nov 21, 2026 | Frontier Airlines | Up to 1 stop each way | Axel-exclusive $290.26 |
| Nov 21, 2026 – Nov 28, 2026 · 7 nights · Compare return dates departing Nov 21, 2026 | Alaska Airlines | Up to 1 stop each way | Axel-exclusive $472.50 |
| Nov 24, 2026 · One way · Compare return dates departing Nov 24, 2026 | Frontier Airlines | Up to 1 stop each way | Axel-exclusive $155.25 |
| Nov 24, 2026 · One way · Compare return dates departing Nov 24, 2026 | Alaska Airlines | Up to 1 stop each way | Axel-exclusive $249.75 |
| Nov 24, 2026 – Nov 29, 2026 · 5 nights · Compare return dates departing Nov 24, 2026 | Frontier Airlines | Up to 1 stop each way | Axel-exclusive $290.26 |
| Nov 24, 2026 – Nov 29, 2026 · 5 nights · Compare return dates departing Nov 24, 2026 | Alaska Airlines | Up to 1 stop each way | Axel-exclusive $472.50 |
| Nov 26, 2026 – Nov 29, 2026 · 3 nights · Compare return dates departing Nov 26, 2026 | Frontier Airlines | Up to 1 stop each way | Axel-exclusive $290.26 |
| Nov 26, 2026 – Nov 29, 2026 · 3 nights · Compare return dates departing Nov 26, 2026 | Alaska Airlines | Up to 1 stop each way | Axel-exclusive $472.50 |
| Nov 27, 2026 – Nov 30, 2026 · 3 nights · Compare return dates departing Nov 27, 2026 | Frontier Airlines | Up to 1 stop each way | Axel-exclusive $290.26 |
| Nov 27, 2026 – Nov 30, 2026 · 3 nights · Compare return dates departing Nov 27, 2026 | Alaska Airlines | Up to 1 stop each way | Axel-exclusive $472.50 |
| Nov 28, 2026 – Dec 5, 2026 · 7 nights · Compare return dates departing Nov 28, 2026 | Frontier Airlines | Up to 1 stop each way | Axel-exclusive $252.63 |
| Nov 28, 2026 – Dec 5, 2026 · 7 nights · Compare return dates departing Nov 28, 2026 | Alaska Airlines | Up to 1 stop each way | Axel-exclusive $411.25 |
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 | Frontier Airlines | Up to 1 stop each way | Axel-exclusive $115.00 |
| Dec 1, 2026 · One way · Compare return dates departing Dec 1, 2026 | Alaska Airlines | Up to 1 stop each way | Axel-exclusive $185.00 |
| Dec 3, 2026 – Dec 6, 2026 · 3 nights · Compare return dates departing Dec 3, 2026 | Frontier Airlines | Up to 1 stop each way | Axel-exclusive $215.00 |
| Dec 3, 2026 – Dec 6, 2026 · 3 nights · Compare return dates departing Dec 3, 2026 | Alaska Airlines | Up to 1 stop each way | Axel-exclusive $350.00 |
| Dec 4, 2026 – Dec 7, 2026 · 3 nights · Compare return dates departing Dec 4, 2026 | Frontier Airlines | Up to 1 stop each way | Axel-exclusive $215.00 |
| Dec 4, 2026 – Dec 7, 2026 · 3 nights · Compare return dates departing Dec 4, 2026 | Alaska Airlines | Up to 1 stop each way | Axel-exclusive $350.00 |
| Dec 5, 2026 – Dec 12, 2026 · 7 nights · Compare return dates departing Dec 5, 2026 | Frontier Airlines | Up to 1 stop each way | Axel-exclusive $215.00 |
| Dec 5, 2026 – Dec 12, 2026 · 7 nights · Compare return dates departing Dec 5, 2026 | Delta Air Lines / Frontier Airlines | Up to 1 stop each way | Axel-exclusive $302.50 |
| Dec 8, 2026 · One way · Compare return dates departing Dec 8, 2026 | Frontier Airlines | Up to 1 stop each way | Axel-exclusive $115.00 |
| Dec 8, 2026 · One way · Compare return dates departing Dec 8, 2026 | Alaska Airlines | Up to 1 stop each way | Axel-exclusive $185.00 |
| Dec 10, 2026 – Dec 13, 2026 · 3 nights · Compare return dates departing Dec 10, 2026 | Frontier Airlines | Up to 1 stop each way | Axel-exclusive $215.00 |
| Dec 10, 2026 – Dec 13, 2026 · 3 nights · Compare return dates departing Dec 10, 2026 | Alaska Airlines | Up to 1 stop each way | Axel-exclusive $350.00 |
| Dec 11, 2026 – Dec 14, 2026 · 3 nights · Compare return dates departing Dec 11, 2026 | Frontier Airlines | Up to 1 stop each way | Axel-exclusive $215.00 |
| Dec 11, 2026 – Dec 14, 2026 · 3 nights · Compare return dates departing Dec 11, 2026 | Alaska Airlines | Up to 1 stop each way | Axel-exclusive $350.00 |
| Dec 12, 2026 – Dec 19, 2026 · 7 nights · Compare return dates departing Dec 12, 2026 | Frontier Airlines | Up to 1 stop each way | Axel-exclusive $258.00 |
| Dec 12, 2026 – Dec 19, 2026 · 7 nights · Compare return dates departing Dec 12, 2026 | Alaska Airlines | Up to 1 stop each way | Axel-exclusive $420.00 |
| Dec 15, 2026 · One way · Compare return dates departing Dec 15, 2026 | Frontier Airlines | Up to 1 stop each way | Axel-exclusive $115.00 |
| Dec 15, 2026 · One way · Compare return dates departing Dec 15, 2026 | Alaska Airlines | Up to 1 stop each way | Axel-exclusive $185.00 |
| Dec 17, 2026 – Dec 20, 2026 · 3 nights · Compare return dates departing Dec 17, 2026 | Frontier Airlines | Up to 1 stop each way | Axel-exclusive $258.00 |
| Dec 17, 2026 – Dec 20, 2026 · 3 nights · Compare return dates departing Dec 17, 2026 | Alaska Airlines | Up to 1 stop each way | Axel-exclusive $420.00 |
| Dec 18, 2026 – Dec 21, 2026 · 3 nights · Compare return dates departing Dec 18, 2026 | Frontier Airlines | Up to 1 stop each way | Axel-exclusive $258.00 |
| Dec 18, 2026 – Dec 21, 2026 · 3 nights · Compare return dates departing Dec 18, 2026 | Alaska Airlines | Up to 1 stop each way | Axel-exclusive $420.00 |
| Dec 19, 2026 – Dec 26, 2026 · 7 nights · Compare return dates departing Dec 19, 2026 | Frontier Airlines | Up to 1 stop each way | Axel-exclusive $301.00 |
| Dec 19, 2026 – Dec 26, 2026 · 7 nights · Compare return dates departing Dec 19, 2026 | Alaska Airlines | Up to 1 stop each way | Axel-exclusive $490.00 |
| Dec 22, 2026 · One way · Compare return dates departing Dec 22, 2026 | Frontier Airlines | Up to 1 stop each way | Axel-exclusive $161.00 |
| Dec 22, 2026 · One way · Compare return dates departing Dec 22, 2026 | Alaska Airlines | Up to 1 stop each way | Axel-exclusive $259.00 |
| Dec 22, 2026 – Dec 27, 2026 · 5 nights · Compare return dates departing Dec 22, 2026 | Frontier Airlines | Up to 1 stop each way | Axel-exclusive $301.00 |
| Dec 22, 2026 – Dec 27, 2026 · 5 nights · Compare return dates departing Dec 22, 2026 | Alaska Airlines | Up to 1 stop each way | Axel-exclusive $490.00 |
| Dec 24, 2026 – Dec 27, 2026 · 3 nights · Compare return dates departing Dec 24, 2026 | Frontier Airlines | Up to 1 stop each way | Axel-exclusive $301.00 |
| Dec 24, 2026 – Dec 27, 2026 · 3 nights · Compare return dates departing Dec 24, 2026 | Alaska Airlines | Up to 1 stop each way | Axel-exclusive $490.00 |
| Dec 25, 2026 – Dec 28, 2026 · 3 nights · Compare return dates departing Dec 25, 2026 | Frontier Airlines | Up to 1 stop each way | Axel-exclusive $301.00 |
| Dec 25, 2026 – Dec 28, 2026 · 3 nights · Compare return dates departing Dec 25, 2026 | Alaska Airlines | Up to 1 stop each way | Axel-exclusive $490.00 |
| Dec 26, 2026 – Jan 2, 2027 · 7 nights · Compare return dates departing Dec 26, 2026 | Frontier Airlines | Up to 1 stop each way | Axel-exclusive $293.48 |
| Dec 26, 2026 – Jan 2, 2027 · 7 nights · Compare return dates departing Dec 26, 2026 | Alaska Airlines | Up to 1 stop each way | Axel-exclusive $477.75 |
| Dec 29, 2026 · One way · Compare return dates departing Dec 29, 2026 | Frontier Airlines | Up to 1 stop each way | Axel-exclusive $161.00 |
| Dec 29, 2026 · One way · Compare return dates departing Dec 29, 2026 | Alaska Airlines | Up to 1 stop each way | Axel-exclusive $259.00 |
| Dec 30, 2026 – Jan 2, 2027 · 3 nights · Compare return dates departing Dec 30, 2026 | Frontier Airlines | Up to 1 stop each way | Axel-exclusive $293.48 |
| Dec 30, 2026 – Jan 2, 2027 · 3 nights · Compare return dates departing Dec 30, 2026 | Alaska Airlines | Up to 1 stop each way | Axel-exclusive $477.75 |
| Dec 31, 2026 – Jan 3, 2027 · 3 nights · Compare return dates departing Dec 31, 2026 | Frontier Airlines | Up to 1 stop each way | Axel-exclusive $293.48 |
| Dec 31, 2026 – Jan 3, 2027 · 3 nights · Compare return dates departing Dec 31, 2026 | Alaska Airlines | Up to 1 stop each way | Axel-exclusive $477.75 |
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 | Frontier Airlines | Up to 1 stop each way | Axel-exclusive $245.11 |
| Jan 1, 2027 – Jan 4, 2027 · 3 nights · Compare return dates departing Jan 1, 2027 | Alaska Airlines | Up to 1 stop each way | Axel-exclusive $399.00 |
| Jan 2, 2027 – Jan 9, 2027 · 7 nights · Compare return dates departing Jan 2, 2027 | Frontier Airlines | Up to 1 stop each way | Axel-exclusive $245.11 |
| Jan 2, 2027 – Jan 9, 2027 · 7 nights · Compare return dates departing Jan 2, 2027 | Alaska Airlines | Up to 1 stop each way | Axel-exclusive $399.00 |
| Jan 5, 2027 · One way · Compare return dates departing Jan 5, 2027 | Frontier Airlines | Up to 1 stop each way | Axel-exclusive $109.25 |
| Jan 5, 2027 · One way · Compare return dates departing Jan 5, 2027 | Alaska Airlines | Up to 1 stop each way | Axel-exclusive $175.75 |
| Jan 7, 2027 – Jan 10, 2027 · 3 nights · Compare return dates departing Jan 7, 2027 | Frontier Airlines | Up to 1 stop each way | Axel-exclusive $204.26 |
| Jan 7, 2027 – Jan 10, 2027 · 3 nights · Compare return dates departing Jan 7, 2027 | Alaska Airlines | Up to 1 stop each way | Axel-exclusive $332.50 |
| Jan 8, 2027 – Jan 11, 2027 · 3 nights · Compare return dates departing Jan 8, 2027 | Frontier Airlines | Up to 1 stop each way | Axel-exclusive $204.26 |
| Jan 8, 2027 – Jan 11, 2027 · 3 nights · Compare return dates departing Jan 8, 2027 | Alaska Airlines | Up to 1 stop each way | Axel-exclusive $332.50 |
| Jan 9, 2027 – Jan 16, 2027 · 7 nights · Compare return dates departing Jan 9, 2027 | Frontier Airlines | Up to 1 stop each way | Axel-exclusive $204.26 |
| Jan 9, 2027 – Jan 16, 2027 · 7 nights · Compare return dates departing Jan 9, 2027 | Alaska Airlines | Up to 1 stop each way | Axel-exclusive $332.50 |
| Jan 12, 2027 · One way · Compare return dates departing Jan 12, 2027 | Frontier Airlines | Up to 1 stop each way | Axel-exclusive $109.25 |
| Jan 12, 2027 · One way · Compare return dates departing Jan 12, 2027 | Alaska Airlines | Up to 1 stop each way | Axel-exclusive $175.75 |
| Jan 14, 2027 – Jan 17, 2027 · 3 nights · Compare return dates departing Jan 14, 2027 | Frontier Airlines | Up to 1 stop each way | Axel-exclusive $204.26 |
| Jan 14, 2027 – Jan 17, 2027 · 3 nights · Compare return dates departing Jan 14, 2027 | Alaska Airlines | Up to 1 stop each way | Axel-exclusive $332.50 |
| Jan 15, 2027 – Jan 18, 2027 · 3 nights · Compare return dates departing Jan 15, 2027 | Frontier Airlines | Up to 1 stop each way | Axel-exclusive $204.26 |
| Jan 15, 2027 – Jan 18, 2027 · 3 nights · Compare return dates departing Jan 15, 2027 | Alaska Airlines | Up to 1 stop each way | Axel-exclusive $332.50 |
| Jan 16, 2027 – Jan 23, 2027 · 7 nights · Compare return dates departing Jan 16, 2027 | Frontier Airlines | Up to 1 stop each way | Axel-exclusive $204.26 |
| Jan 16, 2027 – Jan 23, 2027 · 7 nights · Compare return dates departing Jan 16, 2027 | Alaska Airlines | Up to 1 stop each way | Axel-exclusive $332.50 |
| Jan 19, 2027 · One way · Compare return dates departing Jan 19, 2027 | Frontier Airlines | Up to 1 stop each way | Axel-exclusive $109.25 |
| Jan 19, 2027 · One way · Compare return dates departing Jan 19, 2027 | Alaska Airlines | Up to 1 stop each way | Axel-exclusive $175.75 |
| Jan 21, 2027 – Jan 24, 2027 · 3 nights · Compare return dates departing Jan 21, 2027 | Frontier Airlines | Up to 1 stop each way | Axel-exclusive $204.26 |
| Jan 21, 2027 – Jan 24, 2027 · 3 nights · Compare return dates departing Jan 21, 2027 | Alaska Airlines | Up to 1 stop each way | Axel-exclusive $332.50 |
| Jan 22, 2027 – Jan 25, 2027 · 3 nights · Compare return dates departing Jan 22, 2027 | Frontier Airlines | Up to 1 stop each way | Axel-exclusive $204.26 |
| Jan 22, 2027 – Jan 25, 2027 · 3 nights · Compare return dates departing Jan 22, 2027 | Alaska Airlines | Up to 1 stop each way | Axel-exclusive $332.50 |
| Jan 23, 2027 – Jan 30, 2027 · 7 nights · Compare return dates departing Jan 23, 2027 | Frontier Airlines | Up to 1 stop each way | Axel-exclusive $204.26 |
| Jan 23, 2027 – Jan 30, 2027 · 7 nights · Compare return dates departing Jan 23, 2027 | Alaska Airlines | Up to 1 stop each way | Axel-exclusive $332.50 |
| Jan 26, 2027 · One way · Compare return dates departing Jan 26, 2027 | Frontier Airlines | Up to 1 stop each way | Axel-exclusive $109.25 |
| Jan 26, 2027 · One way · Compare return dates departing Jan 26, 2027 | Alaska Airlines | Up to 1 stop each way | Axel-exclusive $175.75 |
| Jan 28, 2027 – Jan 31, 2027 · 3 nights · Compare return dates departing Jan 28, 2027 | Frontier Airlines | Up to 1 stop each way | Axel-exclusive $204.26 |
| Jan 28, 2027 – Jan 31, 2027 · 3 nights · Compare return dates departing Jan 28, 2027 | Alaska Airlines | Up to 1 stop each way | Axel-exclusive $332.50 |
| Jan 29, 2027 – Feb 1, 2027 · 3 nights · Compare return dates departing Jan 29, 2027 | Frontier Airlines | Up to 1 stop each way | Axel-exclusive $204.26 |
| Jan 29, 2027 – Feb 1, 2027 · 3 nights · Compare return dates departing Jan 29, 2027 | Alaska Airlines | Up to 1 stop each way | Axel-exclusive $332.50 |
| Jan 30, 2027 – Feb 6, 2027 · 7 nights · Compare return dates departing Jan 30, 2027 | Frontier Airlines | Up to 1 stop each way | Axel-exclusive $204.26 |
| Jan 30, 2027 – Feb 6, 2027 · 7 nights · Compare return dates departing Jan 30, 2027 | Alaska Airlines | Up to 1 stop each way | Axel-exclusive $332.50 |
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 | Frontier Airlines | Up to 1 stop each way | Axel-exclusive $109.25 |
| Feb 2, 2027 · One way · Compare return dates departing Feb 2, 2027 | Alaska Airlines | Up to 1 stop each way | Axel-exclusive $175.75 |
| Feb 4, 2027 – Feb 7, 2027 · 3 nights · Compare return dates departing Feb 4, 2027 | Frontier Airlines | Up to 1 stop each way | Axel-exclusive $204.26 |
| Feb 4, 2027 – Feb 7, 2027 · 3 nights · Compare return dates departing Feb 4, 2027 | Alaska Airlines | Up to 1 stop each way | Axel-exclusive $332.50 |
| Feb 5, 2027 – Feb 8, 2027 · 3 nights · Compare return dates departing Feb 5, 2027 | Frontier Airlines | Up to 1 stop each way | Axel-exclusive $204.26 |
| Feb 5, 2027 – Feb 8, 2027 · 3 nights · Compare return dates departing Feb 5, 2027 | Alaska Airlines | Up to 1 stop each way | Axel-exclusive $332.50 |
| Feb 6, 2027 – Feb 13, 2027 · 7 nights · Compare return dates departing Feb 6, 2027 | Frontier Airlines | Up to 1 stop each way | Axel-exclusive $219.31 |
| Feb 6, 2027 – Feb 13, 2027 · 7 nights · Compare return dates departing Feb 6, 2027 | Alaska Airlines | Up to 1 stop each way | Axel-exclusive $357.00 |
| Feb 12, 2027 – Feb 15, 2027 · 3 nights · Compare return dates departing Feb 12, 2027 | Frontier Airlines | Up to 1 stop each way | Axel-exclusive $234.36 |
| Feb 12, 2027 – Feb 15, 2027 · 3 nights · Compare return dates departing Feb 12, 2027 | Alaska Airlines | Up to 1 stop each way | Axel-exclusive $381.50 |
| Feb 19, 2027 – Feb 22, 2027 · 3 nights · Compare return dates departing Feb 19, 2027 | Frontier Airlines | Up to 1 stop each way | Axel-exclusive $204.26 |
| Feb 19, 2027 – Feb 22, 2027 · 3 nights · Compare return dates departing Feb 19, 2027 | Alaska Airlines | Up to 1 stop each way | Axel-exclusive $332.50 |
| Feb 20, 2027 – Feb 27, 2027 · 7 nights · Compare return dates departing Feb 20, 2027 | Frontier Airlines | Up to 1 stop each way | Axel-exclusive $204.26 |
| Feb 20, 2027 – Feb 27, 2027 · 7 nights · Compare return dates departing Feb 20, 2027 | Alaska Airlines | Up to 1 stop each way | Axel-exclusive $332.50 |
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 | Frontier Airlines | Up to 1 stop each way | Axel-exclusive $248.33 |
| Mar 19, 2027 – Mar 22, 2027 · 3 nights · Compare return dates departing Mar 19, 2027 | Alaska Airlines | Up to 1 stop each way | Axel-exclusive $404.25 |
| Mar 20, 2027 – Mar 27, 2027 · 7 nights · Compare return dates departing Mar 20, 2027 | Frontier Airlines | Up to 1 stop each way | Axel-exclusive $270.90 |
| Mar 20, 2027 – Mar 27, 2027 · 7 nights · Compare return dates departing Mar 20, 2027 | Alaska Airlines | Up to 1 stop each way | Axel-exclusive $441.00 |
| Mar 25, 2027 – Mar 29, 2027 · 4 nights · Compare return dates departing Mar 25, 2027 | Frontier Airlines | Up to 1 stop each way | Axel-exclusive $308.70 |
| Mar 25, 2027 – Mar 29, 2027 · 4 nights · Compare return dates departing Mar 25, 2027 | Alaska Airlines | Up to 1 stop each way | Axel-exclusive $485.10 |
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 | Frontier Airlines | Up to 1 stop each way | Axel-exclusive $275.00 |
| Apr 16, 2027 – Apr 19, 2027 · 3 nights · Compare return dates departing Apr 16, 2027 | Alaska Airlines | Up to 1 stop each way | Axel-exclusive $420.00 |
| Apr 17, 2027 – Apr 24, 2027 · 7 nights · Compare return dates departing Apr 17, 2027 | Frontier Airlines | Up to 1 stop each way | Axel-exclusive $275.00 |
| Apr 17, 2027 – Apr 24, 2027 · 7 nights · Compare return dates departing Apr 17, 2027 | Alaska Airlines | Up to 1 stop each way | Axel-exclusive $420.00 |
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 | Frontier Airlines | Up to 1 stop each way | Axel-exclusive $275.00 |
| May 14, 2027 – May 17, 2027 · 3 nights · Compare return dates departing May 14, 2027 | Alaska Airlines | Up to 1 stop each way | Axel-exclusive $420.00 |
| May 15, 2027 – May 22, 2027 · 7 nights · Compare return dates departing May 15, 2027 | Frontier Airlines | Up to 1 stop each way | Axel-exclusive $275.00 |
| May 15, 2027 – May 22, 2027 · 7 nights · Compare return dates departing May 15, 2027 | Alaska Airlines | Up to 1 stop each way | Axel-exclusive $420.00 |
| May 28, 2027 – May 31, 2027 · 3 nights · Compare return dates departing May 28, 2027 | Frontier Airlines | Up to 1 stop each way | Axel-exclusive $330.00 |
| May 28, 2027 – May 31, 2027 · 3 nights · Compare return dates departing May 28, 2027 | Alaska Airlines | Up to 1 stop each way | Axel-exclusive $504.00 |
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 | Frontier Airlines | Up to 1 stop each way | Axel-exclusive $275.00 |
| Jun 11, 2027 – Jun 14, 2027 · 3 nights · Compare return dates departing Jun 11, 2027 | Alaska Airlines | Up to 1 stop each way | Axel-exclusive $420.00 |
| Jun 12, 2027 – Jun 19, 2027 · 7 nights · Compare return dates departing Jun 12, 2027 | Frontier Airlines | Up to 1 stop each way | Axel-exclusive $275.00 |
| Jun 12, 2027 – Jun 19, 2027 · 7 nights · Compare return dates departing Jun 12, 2027 | Alaska Airlines | Up to 1 stop each way | Axel-exclusive $420.00 |
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 | Frontier Airlines | Up to 1 stop each way | Axel-exclusive $346.50 |
| Jul 2, 2027 – Jul 6, 2027 · 4 nights · Compare return dates departing Jul 2, 2027 | Delta Air Lines / Frontier Airlines | Up to 1 stop each way | Axel-exclusive $463.05 |
| Jul 9, 2027 – Jul 12, 2027 · 3 nights · Compare return dates departing Jul 9, 2027 | Frontier Airlines | Up to 1 stop each way | Axel-exclusive $288.76 |
| Jul 9, 2027 – Jul 12, 2027 · 3 nights · Compare return dates departing Jul 9, 2027 | Alaska Airlines | Up to 1 stop each way | Axel-exclusive $441.00 |
| Jul 10, 2027 – Jul 17, 2027 · 7 nights · Compare return dates departing Jul 10, 2027 | Frontier Airlines | Up to 1 stop each way | Axel-exclusive $288.76 |
| Jul 10, 2027 – Jul 17, 2027 · 7 nights · Compare return dates departing Jul 10, 2027 | Alaska Airlines | Up to 1 stop each way | Axel-exclusive $441.00 |
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 | Frontier Airlines | Up to 1 stop each way | Axel-exclusive $275.00 |
| Aug 6, 2027 – Aug 9, 2027 · 3 nights · Compare return dates departing Aug 6, 2027 | Alaska Airlines | Up to 1 stop each way | Axel-exclusive $420.00 |
| Aug 7, 2027 – Aug 14, 2027 · 7 nights · Compare return dates departing Aug 7, 2027 | Frontier Airlines | Up to 1 stop each way | Axel-exclusive $275.00 |
| Aug 7, 2027 – Aug 14, 2027 · 7 nights · Compare return dates departing Aug 7, 2027 | Alaska Airlines | Up to 1 stop each way | Axel-exclusive $420.00 |
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 | Frontier Airlines | Up to 1 stop each way | Axel-exclusive $313.50 |
| Sep 3, 2027 – Sep 6, 2027 · 3 nights · Compare return dates departing Sep 3, 2027 | Alaska Airlines | Up to 1 stop each way | Axel-exclusive $478.80 |
| Sep 4, 2027 – Sep 11, 2027 · 7 nights · Compare return dates departing Sep 4, 2027 | Frontier Airlines | Up to 1 stop each way | Axel-exclusive $287.38 |
| Sep 4, 2027 – Sep 11, 2027 · 7 nights · Compare return dates departing Sep 4, 2027 | Alaska Airlines | Up to 1 stop each way | Axel-exclusive $438.90 |
| Sep 24, 2027 – Sep 27, 2027 · 3 nights · Compare return dates departing Sep 24, 2027 | Frontier Airlines | Up to 1 stop each way | Axel-exclusive $261.26 |
| Sep 24, 2027 – Sep 27, 2027 · 3 nights · Compare return dates departing Sep 24, 2027 | Alaska Airlines | Up to 1 stop each way | Axel-exclusive $399.00 |
| Sep 25, 2027 – Oct 2, 2027 · 7 nights · Compare return dates departing Sep 25, 2027 | Frontier Airlines | Up to 1 stop each way | Axel-exclusive $268.13 |
| Sep 25, 2027 – Oct 2, 2027 · 7 nights · Compare return dates departing Sep 25, 2027 | Alaska Airlines | Up to 1 stop each way | Axel-exclusive $409.50 |
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, $480 total · 4★ The Chicago Hotel Collection Ambassador Gold Coast, $206 total · 5★ Nobu Hotel Chicago, $1,410 total
- Hotels in Chicago for these nights (Nov 20–23, 2026 · 3 nights · 2 adults, 1 room): 3★ Congress Plaza Hotel, $472 total · 4★ The Chicago Hotel Collection Ambassador Gold Coast, $206 total · 5★ Nobu Hotel Chicago, $1,262 total
- Hotels in Chicago for these nights (Nov 21–28, 2026 · 7 nights · 2 adults, 1 room): 3★ Congress Plaza Hotel, $873 total · 4★ The Chicago Hotel Collection Ambassador Gold Coast, $395 total · 5★ Nobu Hotel Chicago, $2,423 total
- Hotels in Chicago for these nights (Nov 24–29, 2026 · 5 nights · 2 adults, 1 room): 3★ The Whitehall Hotel, BW Premier Collection, $625 total · 4★ The Chicago Hotel Collection Ambassador Gold Coast, $328 total · 5★ Sofitel Chicago Magnificent Mile, $1,266 total
- Hotels in Chicago for these nights (Nov 26–29, 2026 · 3 nights · 2 adults, 1 room): 3★ The Whitehall Hotel, BW Premier Collection, $438 total · 4★ Freehand Chicago, $258 total · 5★ Sofitel Chicago Magnificent Mile, $824 total
- 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 · 4★ Freehand Chicago, $259 total · 5★ Sofitel Chicago Magnificent Mile, $918 total
- Hotels in Chicago for these nights (Nov 28 – Dec 5, 2026 · 7 nights · 2 adults, 1 room): 3★ Hotel Versey, $810 total · 4★ Freehand Chicago, $590 total · 5★ Sofitel Chicago Magnificent Mile, $2,057 total
- Hotels in Chicago for these nights (Dec 3–6, 2026 · 3 nights · 2 adults, 1 room): 3★ Congress Plaza Hotel, $369 total · 4★ Freehand Chicago, $246 total · 5★ Sofitel Chicago Magnificent Mile, $848 total
- Hotels in Chicago for these nights (Dec 4–7, 2026 · 3 nights · 2 adults, 1 room): 3★ Congress Plaza Hotel, $345 total · 4★ The Chicago Hotel Collection Ambassador Gold Coast, $220 total · 5★ Sofitel Chicago Magnificent Mile, $841 total
- Hotels in Chicago for these nights (Dec 5–12, 2026 · 7 nights · 2 adults, 1 room): 3★ The Whitehall Hotel, BW Premier Collection, $735 total · 4★ The Chicago Hotel Collection Ambassador Gold Coast, $281 total · 5★ Nobu Hotel Chicago, $2,855 total
- Hotels in Chicago for these nights (Dec 10–13, 2026 · 3 nights · 2 adults, 1 room): 3★ Congress Plaza Hotel, $348 total · 4★ The Chicago Hotel Collection Ambassador Gold Coast, $209 total · 5★ Sofitel Chicago Magnificent Mile, $985 total
- Hotels in Chicago for these nights (Dec 11–14, 2026 · 3 nights · 2 adults, 1 room): 3★ Congress Plaza Hotel, $349 total · 4★ The Chicago Hotel Collection Ambassador Gold Coast, $157 total · 5★ Sofitel Chicago Magnificent Mile, $960 total
- Hotels in Chicago for these nights (Dec 12–19, 2026 · 7 nights · 2 adults, 1 room): 3★ Hotel Versey, $681 total · 4★ The Chicago Hotel Collection Ambassador Gold Coast, $233 total · 5★ Sofitel Chicago Magnificent Mile, $1,663 total
- Hotels in Chicago for these nights (Dec 17–20, 2026 · 3 nights · 2 adults, 1 room): 3★ The Whitehall Hotel, BW Premier Collection, $325 total · 4★ The Chicago Hotel Collection Ambassador Gold Coast, $157 total · 5★ Sofitel Chicago Magnificent Mile, $726 total
- Hotels in Chicago for these nights (Dec 18–21, 2026 · 3 nights · 2 adults, 1 room): 3★ Hotel Versey, $316 total · 4★ The Chicago Hotel Collection Ambassador Gold Coast, $157 total · 5★ Sofitel Chicago Magnificent Mile, $718 total
- Hotels in Chicago for these nights (Dec 19–26, 2026 · 7 nights · 2 adults, 1 room): 3★ Hotel Versey, $712 total · 4★ The Chicago Hotel Collection Ambassador Gold Coast, $274 total · 5★ Sofitel Chicago Magnificent Mile, $1,687 total
- Hotels in Chicago for these nights (Dec 22–27, 2026 · 5 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $477 total · 4★ The Chicago Hotel Collection Ambassador Gold Coast, $209 total · 5★ Sofitel Chicago Magnificent Mile, $1,173 total
- Hotels in Chicago for these nights (Dec 24–27, 2026 · 3 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $289 total · 4★ The Chicago Hotel Collection Ambassador Gold Coast, $171 total · 5★ Sofitel Chicago Magnificent Mile, $688 total
- Hotels in Chicago for these nights (Dec 25–28, 2026 · 3 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $277 total · 4★ The Chicago Hotel Collection Ambassador Gold Coast, $171 total · 5★ Sofitel Chicago Magnificent Mile, $708 total
- Hotels in Chicago for these nights (Dec 26 – Jan 2, 2027 · 7 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $833 total · 4★ The Chicago Hotel Collection Ambassador Gold Coast, $512 total · 5★ Sofitel Chicago Magnificent Mile, $1,886 total
- Hotels in Chicago for these nights (Dec 30 – Jan 2, 2027 · 3 nights · 2 adults, 1 room): 3★ The Willows Hotel, $424 total · 4★ Freehand Chicago, $335 total · 5★ Sofitel Chicago Magnificent Mile, $873 total
- Hotels in Chicago for these nights (Dec 31 – Jan 3, 2027 · 3 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $408 total · 4★ Freehand Chicago, $332 total · 5★ Sofitel Chicago Magnificent Mile, $874 total
- Hotels in Chicago for these nights (Jan 1–4, 2027 · 3 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $231 total · 4★ The Chicago Hotel Collection Ambassador Gold Coast, $128 total · 5★ Sofitel Chicago Magnificent Mile, $671 total
- Hotels in Chicago for these nights (Jan 2–9, 2027 · 7 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $543 total · 4★ The Chicago Hotel Collection Ambassador Gold Coast, $315 total · 5★ Sofitel Chicago Magnificent Mile, $1,620 total
- Hotels in Chicago for these nights (Jan 7–10, 2027 · 3 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $231 total · 4★ The Chicago Hotel Collection Ambassador Gold Coast, $194 total · 5★ Sofitel Chicago Magnificent Mile, $724 total
- Hotels in Chicago for these nights (Jan 8–11, 2027 · 3 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $231 total · 4★ The Chicago Hotel Collection Ambassador Gold Coast, $194 total · 5★ Sofitel Chicago Magnificent Mile, $679 total
- Hotels in Chicago for these nights (Jan 9–16, 2027 · 7 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $520 total · 4★ The Chicago Hotel Collection Ambassador Gold Coast, $357 total · 5★ Sofitel Chicago Magnificent Mile, $1,504 total
- Hotels in Chicago for these nights (Jan 14–17, 2027 · 3 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $216 total · 4★ The Chicago Hotel Collection Ambassador Gold Coast, $71 total · 5★ Sofitel Chicago Magnificent Mile, $726 total
- Hotels in Chicago for these nights (Jan 15–18, 2027 · 3 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $224 total · 4★ The Chicago Hotel Collection Ambassador Gold Coast, $71 total · 5★ Sofitel Chicago Magnificent Mile, $722 total
- Hotels in Chicago for these nights (Jan 16–23, 2027 · 7 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $542 total · 4★ The Chicago Hotel Collection Ambassador Gold Coast, $374 total · 5★ Sofitel Chicago Magnificent Mile, $1,613 total
- Hotels in Chicago for these nights (Jan 21–24, 2027 · 3 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $219 total · 4★ The Chicago Hotel Collection Ambassador Gold Coast, $213 total · 5★ Sofitel Chicago Magnificent Mile, $1,045 total
- Hotels in Chicago for these nights (Jan 22–25, 2027 · 3 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $216 total · 4★ Freehand Chicago, $230 total · 5★ Nobu Hotel Chicago, $1,093 total
- Hotels in Chicago for these nights (Jan 23–30, 2027 · 7 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $528 total · 4★ Freehand Chicago, $514 total · 5★ Nobu Hotel Chicago, $2,588 total
- Hotels in Chicago for these nights (Jan 28–31, 2027 · 3 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $231 total · 4★ Freehand Chicago, $229 total · 5★ Sofitel Chicago Magnificent Mile, $787 total
- Hotels in Chicago for these nights (Jan 29 – Feb 1, 2027 · 3 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $231 total · 4★ The Chicago Hotel Collection Ambassador Gold Coast, $204 total · 5★ Sofitel Chicago Magnificent Mile, $791 total
- Hotels in Chicago for these nights (Jan 30 – Feb 6, 2027 · 7 nights · 2 adults, 1 room): 3★ Hotel Versey, $616 total · 4★ The Chicago Hotel Collection Ambassador Gold Coast, $192 total · 5★ Sofitel Chicago Magnificent Mile, $1,851 total
- Hotels in Chicago for these nights (Feb 4–7, 2027 · 3 nights · 2 adults, 1 room): 3★ Hotel Versey, $295 total · 4★ The Chicago Hotel Collection Ambassador Gold Coast, $112 total · 5★ Sofitel Chicago Magnificent Mile, $794 total
- Hotels in Chicago for these nights (Feb 5–8, 2027 · 3 nights · 2 adults, 1 room): 3★ Hotel Versey, $294 total · 4★ The Chicago Hotel Collection Ambassador Gold Coast, $112 total · 5★ Sofitel Chicago Magnificent Mile, $794 total
- Hotels in Chicago for these nights (Feb 6–13, 2027 · 7 nights · 2 adults, 1 room): 3★ Hotel Versey, $642 total · 4★ The Chicago Hotel Collection Ambassador Gold Coast, $375 total · 5★ Sofitel Chicago Magnificent Mile, $1,822 total
- Hotels in Chicago for these nights (Feb 12–15, 2027 · 3 nights · 2 adults, 1 room): 3★ Hotel Versey, $379 total · 4★ The Chicago Hotel Collection Ambassador Gold Coast, $279 total · 5★ Sofitel Chicago Magnificent Mile, $777 total
- Hotels in Chicago for these nights (Feb 19–22, 2027 · 3 nights · 2 adults, 1 room): 3★ Hotel Versey, $324 total · 4★ The Chicago Hotel Collection Ambassador Gold Coast, $112 total · 5★ Sofitel Chicago Magnificent Mile, $773 total
- Hotels in Chicago for these nights (Feb 20–27, 2027 · 7 nights · 2 adults, 1 room): 3★ Hotel Versey, $642 total · 4★ The Chicago Hotel Collection Ambassador Gold Coast, $216 total · 5★ Sofitel Chicago Magnificent Mile, $1,813 total
- Hotels in Chicago for these nights (Mar 19–22, 2027 · 3 nights · 2 adults, 1 room): 3★ Hotel Versey, $360 total · 4★ Freehand Chicago, $293 total · 5★ Sofitel Chicago Magnificent Mile, $1,029 total
- Hotels in Chicago for these nights (Mar 20–27, 2027 · 7 nights · 2 adults, 1 room): 3★ Hotel Versey, $854 total · 4★ Freehand Chicago, $654 total · 5★ Sofitel Chicago Magnificent Mile, $2,406 total
- Hotels in Chicago for these nights (Mar 25–29, 2027 · 4 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $562 total · 4★ Freehand Chicago, $383 total · 5★ Sofitel Chicago Magnificent Mile, $1,394 total
- Hotels in Chicago for these nights (Apr 16–19, 2027 · 3 nights · 2 adults, 1 room): 3★ Hotel Versey, $537 total · 4★ Freehand Chicago, $374 total · 5★ Nobu Hotel Chicago, $1,199 total
- Hotels in Chicago for these nights (Apr 17–24, 2027 · 7 nights · 2 adults, 1 room): 3★ Hotel Versey, $1,032 total · 4★ Freehand Chicago, $832 total · 5★ Nobu Hotel Chicago, $3,023 total
- Hotels in Chicago for these nights (May 14–17, 2027 · 3 nights · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ Warwick Allerton - Chicago · 5★ The Langham, Chicago
- Hotels in Chicago for these nights (May 15–22, 2027 · 7 nights · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ Warwick Allerton - Chicago · 5★ The Langham, Chicago
- Hotels in Chicago for these nights (May 28–31, 2027 · 3 nights · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ Warwick Allerton - Chicago · 5★ The Langham, Chicago
- Hotels in Chicago for these nights (Jun 11–14, 2027 · 3 nights · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ Warwick Allerton - Chicago · 5★ The Langham, Chicago
- Hotels in Chicago for these nights (Jun 12–19, 2027 · 7 nights · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ Warwick Allerton - Chicago · 5★ The Langham, Chicago
- Hotels in Chicago for these nights (Jul 2–6, 2027 · 4 nights · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ Warwick Allerton - Chicago · 5★ The Langham, Chicago
- Hotels in Chicago for these nights (Jul 9–12, 2027 · 3 nights · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ Warwick Allerton - Chicago · 5★ The Langham, Chicago
- Hotels in Chicago for these nights (Jul 10–17, 2027 · 7 nights · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ Warwick Allerton - Chicago · 5★ The Langham, Chicago
- Hotels in Chicago for these nights (Aug 6–9, 2027 · 3 nights · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ Warwick Allerton - Chicago · 5★ The Langham, Chicago
- Hotels in Chicago for these nights (Aug 7–14, 2027 · 7 nights · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ Warwick Allerton - Chicago · 5★ The Langham, Chicago
- Hotels in Chicago for these nights (Sep 3–6, 2027 · 3 nights · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ Warwick Allerton - Chicago · 5★ The Langham, Chicago
- Hotels in Chicago for these nights (Sep 4–11, 2027 · 7 nights · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ Warwick Allerton - Chicago · 5★ The Langham, Chicago
- Hotels in Chicago for these nights (Sep 24–27, 2027 · 3 nights · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ Warwick Allerton - Chicago · 5★ The Langham, Chicago
- Hotels in Chicago for these nights (Sep 25 – Oct 2, 2027 · 7 nights · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ Warwick Allerton - Chicago · 5★ The Langham, Chicago
Route overview: San Francisco Bay Area to Chicago (ORD) flight deals
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
- Nov 27, 2026 · Return options
- Dec 8, 2026 · Return options
- Dec 19, 2026 · Return options
- Dec 29, 2026 · Return options
- Jan 8, 2027 · Return options
- Jan 19, 2027 · Return options
- Jan 30, 2027 · Return options
- Feb 19, 2027 · Return options
- May 14, 2027 · Return options
- Jul 9, 2027 · Return options
- Sep 25, 2027 · Return options
- Hotels in Chicago with Axel
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 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 · Flight search guide.
- 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_fallbackusing IATA airport codes and the traveler’s known details. Omit unknowns; for one way replace/return/YYYY-MM-DDwith/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.
Feedback (optional): Missing info · Axel issue