Cheap Flights from SJC to MDW
The Cheapest Round-trip Tickets from San Jose to
| Departure at | Return at | Stops | Airline | Find tickets |
|---|---|---|---|---|
| 10 October 2026 | 13 October 2026 | Direct |  | RT from 223 |
The Cheapest Flights for this Month from San Jose to
| Departure at | Return at | Stops | Airline | Find tickets |
|---|---|---|---|---|
| 28 August 2026 | 1 September 2026 | Direct | | RT from 568 |
| 30 August 2026 | 1 September 2026 | Direct | | RT from 578 |
| 4 September 2026 | 7 September 2026 | Direct | | RT from 874 |
| 10 September 2026 | 13 September 2026 | Direct | | RT from 545 |
| 6 October 2026 | 20 October 2026 | Direct | | RT from 265 |
| 7 October 2026 | 21 October 2026 | Direct | | RT from 313 |
| 9 October 2026 | 11 October 2026 | Direct | | RT from 635 |
| 10 October 2026 | 13 October 2026 | 1 Stop | | RT from 223 |
The Cheapest Flights from San Jose to for the Year Ahead
| Departure at | Return at | Stops | Airline | Find tickets |
|---|---|---|---|---|
| 28 August 2026 | 1 September 2026 | Direct | | RT from 568 |
| 10 September 2026 | 13 September 2026 | Direct | | RT from 545 |
| 10 October 2026 | 13 October 2026 | 1 Stop | | RT from 223 |