Cheap Flights from OAK to MDW
The Cheapest Round-trip Tickets from Oakland to
| Departure at | Return at | Stops | Airline | Find tickets |
|---|---|---|---|---|
| 11 May 2026 | 15 May 2026 | Direct |  | RT from 342 |
The Cheapest Flights for this Month from Oakland to
| Departure at | Return at | Stops | Airline | Find tickets |
|---|---|---|---|---|
| 14 February 2026 | 16 February 2026 | Direct | | RT from 1 130 |
| 3 March 2026 | 4 March 2026 | Direct | | RT from 523 |
| 11 May 2026 | 15 May 2026 | Direct | | RT from 342 |
| 15 May 2026 | 17 May 2026 | Direct | | RT from 553 |
The Cheapest Flights from Oakland to for the Year Ahead
| Departure at | Return at | Stops | Airline | Find tickets |
|---|---|---|---|---|
| 14 February 2026 | 16 February 2026 | Direct | | RT from 1 130 |
| 3 March 2026 | 4 March 2026 | Direct | | RT from 523 |
| 11 May 2026 | 15 May 2026 | Direct | | RT from 342 |