Cheap Flights from OAK to CHI
The Cheapest Round-trip Tickets from Oakland to Chicago
| Departure at | Return at | Stops | Airline | Find tickets |
|---|---|---|---|---|
| 7 September 2026 | 14 September 2026 | Direct |  | RT from 146 |
The Cheapest Flights for this Month from Oakland to Chicago
| Departure at | Return at | Stops | Airline | Find tickets |
|---|---|---|---|---|
| 20 July 2026 | 23 July 2026 | 1 Stop |  | RT from 527 |
| 31 July 2026 | 8 August 2026 | 1 Stop | | RT from 442 |
| 1 August 2026 | 9 August 2026 | Direct | | RT from 515 |
| 2 August 2026 | 7 August 2026 | Direct | | RT from 494 |
| 3 August 2026 | 7 August 2026 | Direct | | RT from 512 |
| 6 August 2026 | 9 August 2026 | 1 Stop | | RT from 378 |
| 27 August 2026 | 30 August 2026 | 1 Stop | | RT from 283 |
| 7 September 2026 | 14 September 2026 | 1 Stop | | RT from 146 |
| 7 October 2026 | 12 October 2026 | Direct | | RT from 436 |
| 5 February 2027 | 11 February 2027 | 1 Stop | | RT from 332 |
| 26 March 2027 | 29 March 2027 | 1 Stop | | RT from 385 |
| 27 March 2027 | 29 March 2027 | 1 Stop | | RT from 461 |
The Cheapest Flights from Oakland to Chicago for the Year Ahead
| Departure at | Return at | Stops | Airline | Find tickets |
|---|---|---|---|---|
| 31 July 2026 | 8 August 2026 | 1 Stop | | RT from 442 |
| 27 August 2026 | 30 August 2026 | 1 Stop | | RT from 283 |
| 7 September 2026 | 14 September 2026 | 1 Stop | | RT from 146 |
| 7 October 2026 | 12 October 2026 | Direct | | RT from 436 |
| 5 February 2027 | 11 February 2027 | 1 Stop | | RT from 332 |
| 26 March 2027 | 29 March 2027 | 1 Stop | | RT from 385 |