Cheap Flights from OAK to MDW
The Cheapest Round-trip Tickets from Oakland to
| Departure at | Return at | Stops | Airline | Find tickets |
|---|---|---|---|---|
| 3 November 2026 | 5 November 2026 | Direct |  | RT from 351 USD |
The Cheapest Flights for this Month from Oakland to
| Departure at | Return at | Stops | Airline | Find tickets |
|---|---|---|---|---|
| 18 October 2026 | 20 October 2026 | Direct | | RT from 628 USD |
| 19 October 2026 | 22 October 2026 | Direct | | RT from 518 USD |
| 21 October 2026 | 30 October 2026 | Direct | | RT from 438 USD |
| 3 November 2026 | 5 November 2026 | Direct | | RT from 351 USD |
| 8 November 2026 | 14 November 2026 | Direct | | RT from 403 USD |
| 20 November 2026 | 24 November 2026 | 1 Stop | | RT from 467 USD |
| 1 March 2027 | 4 March 2027 | 1 Stop | | RT from 354 USD |
| 5 May 2027 | 18 May 2027 | Direct | | RT from 380 USD |
| 1 June 2027 | 4 June 2027 | 1 Stop | | RT from 416 USD |
The Cheapest Flights from Oakland to for the Year Ahead
| Departure at | Return at | Stops | Airline | Find tickets |
|---|---|---|---|---|
| 21 October 2026 | 30 October 2026 | Direct | | RT from 438 USD |
| 3 November 2026 | 5 November 2026 | Direct | | RT from 351 USD |
| 1 March 2027 | 4 March 2027 | 1 Stop | | RT from 354 USD |
| 5 May 2027 | 18 May 2027 | Direct | | RT from 380 USD |
| 1 June 2027 | 4 June 2027 | 1 Stop | | RT from 416 USD |