Cheap Flights from OAK to MDW
The Cheapest Round-trip Tickets from Oakland to
| Departure at | Return at | Stops | Airline | Find tickets |
|---|---|---|---|---|
| 1 May 2026 | 9 May 2026 | Direct |  | RT from 355 |
The Cheapest Flights for this Month from Oakland to
| Departure at | Return at | Stops | Airline | Find tickets |
|---|---|---|---|---|
| 24 November 2025 | 27 November 2025 | 1 Stop | | RT from 380 |
| 25 November 2025 | 28 November 2025 | Direct | | RT from 809 |
| 22 December 2025 | 25 December 2025 | Direct | | RT from 692 |
| 3 January 2026 | 5 January 2026 | Direct | | RT from 603 |
| 1 May 2026 | 9 May 2026 | Direct | | RT from 355 |
The Cheapest Flights from Oakland to for the Year Ahead
| Departure at | Return at | Stops | Airline | Find tickets |
|---|---|---|---|---|
| 24 November 2025 | 27 November 2025 | 1 Stop | | RT from 380 |
| 22 December 2025 | 25 December 2025 | Direct | | RT from 692 |
| 3 January 2026 | 5 January 2026 | Direct | | RT from 603 |
| 1 May 2026 | 9 May 2026 | Direct | | RT from 355 |