Cheap Flights from MDW to OAK
The Cheapest Round-trip Tickets from to Oakland
| Departure at | Return at | Stops | Airline | Find tickets |
|---|---|---|---|---|
| 7 November 2026 | 9 November 2026 | Direct |  | RT from 368 USD |
The Cheapest Flights for this Month from to Oakland
| Departure at | Return at | Stops | Airline | Find tickets |
|---|---|---|---|---|
| 21 October 2026 | 25 October 2026 | Direct | | RT from 606 USD |
| 23 October 2026 | 25 October 2026 | Direct | | RT from 658 USD |
| 30 October 2026 | 2 November 2026 | Direct | | RT from 675 USD |
| 7 November 2026 | 9 November 2026 | Direct | | RT from 368 USD |
| 8 November 2026 | 20 November 2026 | 1 Stop | | RT from 484 USD |
| 13 November 2026 | 16 November 2026 | Direct | | RT from 374 USD |
| 18 November 2026 | 21 November 2026 | 1 Stop | | RT from 380 USD |
| 25 November 2026 | 7 December 2026 | Direct | | RT from 405 USD |
| 18 December 2026 | 5 January 2027 | Direct | | RT from 374 USD |
| 14 April 2027 | 18 April 2027 | Direct | | RT from 450 USD |
| 15 April 2027 | 18 April 2027 | Direct | | RT from 470 USD |
| 18 April 2027 | 25 April 2027 | Direct | | RT from 593 USD |
The Cheapest Flights from to Oakland for the Year Ahead
| Departure at | Return at | Stops | Airline | Find tickets |
|---|---|---|---|---|
| 21 October 2026 | 25 October 2026 | Direct | | RT from 606 USD |
| 7 November 2026 | 9 November 2026 | Direct | | RT from 368 USD |
| 18 December 2026 | 5 January 2027 | Direct | | RT from 374 USD |
| 14 April 2027 | 18 April 2027 | Direct | | RT from 450 USD |