Cheap flights from Chicago to Oakland
Find cheap Oakland to Chicago flights with our free search service. Compare all available fares for direct or connection flights from Oakland to Chicago.
Chicago to Oakland flight schedules
| Flight | Departure Date | Arrival Date | Price | Duration | Number of stops | Updated |
|---|---|---|---|---|---|---|
| Chicago (CHI) - Oakland (OAK) | 2026-12-01 | 2026-12-04 | 359 USD | 27 hours 44 minutes | Connection | 2026-09-26T19:30:13 |
| Chicago (CHI) - Oakland (SFO) | 2026-10-16 | 2026-10-19 | 361 USD | 8 hours 55 minutes | Direct | 2026-09-24T06:57:42 |
| Chicago (CHI) - Oakland (OAK) | 2026-11-01 | 2026-11-04 | 429 USD | 8 hours 50 minutes | Direct | 2026-09-27T01:41:42 |
| Chicago (CHI) - Oakland (SFO) | 2026-10-01 | 2026-10-04 | 660 USD | 8 hours 45 minutes | Direct | 2026-09-25T13:31:55 |
Chicago to Oakland flight status
| Flight | Origin | Destination | Departure | Arrival | Equip |
|---|---|---|---|---|---|
| B61173 | Chicago (MDW) | Oakland (OAK) | 3:25 p.m. | 5:03 p.m. | |
| WN2113 | Chicago (MDW) | Oakland (OAK) | 5:40 a.m. | 7:15 a.m. | B738 |
| WN1527 | Chicago (MDW) | Oakland (OAK) | 5:40 p.m. | 8:10 p.m. | B738 |
| WN4133 | Chicago (MDW) | Oakland (OAK) | 10:40 a.m. | 12:05 p.m. | B737 |
| WN1688 | Chicago (MDW) | Oakland (OAK) | 7:40 p.m. | 12:40 a.m. | B737 |
| WN1185 | Chicago (MDW) | Oakland (OAK) | 1:45 p.m. | 3 p.m. | B738 |
| WN3372 | Chicago (MDW) | Oakland (OAK) | 8 a.m. | 10:15 a.m. | B738 |
| WN5347 | Chicago (MDW) | Oakland (OAK) | 9:55 a.m. | 12:20 p.m. | B737 |
| WN6804 | Chicago (MDW) | Oakland (OAK) | 9:35 a.m. | 11:15 a.m. | B737 |
| WN6593 | Chicago (MDW) | Oakland (OAK) | 3:05 p.m. | 6:50 p.m. | B737 |
| WQ4529 | Chicago (MDW) | Oakland (OAK) | 5:30 p.m. | 8:33 p.m. | B738 |
| HG2287 | Chicago (MDW) | Oakland (OAK) | 7:05 a.m. | 3 p.m. | 320 |
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