Cheap flights from Oakland to Chicago
Find cheap Chicago to Oakland flights with our free search service. Compare all available fares for direct or connection flights from Chicago to Oakland.
Oakland to Chicago flight schedules
| Flight | Departure Date | Arrival Date | Price | Duration | Number of stops | Updated |
|---|---|---|---|---|---|---|
| Oakland (OAK) - Chicago (CHI) | 2026-12-07 | 2026-12-14 | 367 USD | 8 hours 50 minutes | Direct | 2026-11-08T12:38:07 |
| Oakland (OAK) - Chicago (CHI) | 2026-12-07 | 2026-12-10 | 384 USD | 8 hours 50 minutes | Direct | 2026-11-08T09:05:14 |
| Oakland (OAK) - Chicago (CHI) | 2026-11-20 | 2026-11-25 | 448 USD | 12 hours 15 minutes | Direct | 2026-11-04T01:47:04 |
| Oakland (OAK) - Chicago (CHI) | 2027-04-06 | 2027-04-13 | 451 USD | 8 hours 50 minutes | Direct | 2026-11-06T02:07:52 |
| Oakland (OAK) - Chicago (CHI) | 2026-11-10 | 2026-11-12 | 586 USD | 8 hours 55 minutes | Direct | 2026-11-07T19:41:08 |
| Oakland (OAK) - Chicago (CHI) | 2026-11-16 | 2026-11-19 | 590 USD | 8 hours 55 minutes | Direct | 2026-11-04T11:37:00 |
| Oakland (OAK) - Chicago (CHI) | 2026-11-23 | 2026-11-30 | 592 USD | 12 hours 5 minutes | Connection | 2026-11-08T15:41:34 |
| Oakland (OAK) - Chicago (CHI) | 2026-11-09 | 2026-11-12 | 597 USD | 12 hours 10 minutes | Direct | 2026-11-07T19:42:27 |
| Oakland (OAK) - Chicago (CHI) | 2026-11-13 | 2026-11-16 | 598 USD | 8 hours 50 minutes | Direct | 2026-11-04T18:14:49 |
| Oakland (OAK) - Chicago (CHI) | 2026-11-19 | 2026-11-22 | 721 USD | 8 hours 55 minutes | Direct | 2026-11-05T22:43:45 |
Oakland to Chicago flight status
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