Cheap Flights from OAK to CHI
The Cheapest Round-trip Tickets from Oakland to Chicago
| Departure at | Return at | Stops | Airline | Find tickets |
|---|---|---|---|---|
| 27 August 2026 | 30 August 2026 | Direct |  | RT from 332 |
The Cheapest Flights for this Month from Oakland to Chicago
| Departure at | Return at | Stops | Airline | Find tickets |
|---|---|---|---|---|
| 14 July 2026 | 16 July 2026 | 1 Stop | | RT from 603 |
| 18 July 2026 | 21 July 2026 | Direct |  | RT from 591 |
| 6 August 2026 | 9 August 2026 | 1 Stop | | RT from 378 |
| 16 August 2026 | 19 August 2026 | Direct | | RT from 332 |
| 27 August 2026 | 30 August 2026 | 1 Stop | | RT from 332 |
| 7 October 2026 | 12 October 2026 | Direct | | RT from 436 |
The Cheapest Flights from Oakland to Chicago for the Year Ahead
| Departure at | Return at | Stops | Airline | Find tickets |
|---|---|---|---|---|
| 18 July 2026 | 21 July 2026 | Direct | | RT from 591 |
| 27 August 2026 | 30 August 2026 | 1 Stop | | RT from 332 |
| 7 October 2026 | 12 October 2026 | Direct | | RT from 436 |