Cheap Flights from SJC to CHI
The Cheapest Round-trip Tickets from San Jose to Chicago
| Departure at | Return at | Stops | Airline | Find tickets |
|---|---|---|---|---|
| 9 July 2026 | 13 July 2026 | Direct |  | RT from 306 |
The Cheapest Flights for this Month from San Jose to Chicago
| Departure at | Return at | Stops | Airline | Find tickets |
|---|---|---|---|---|
| 6 June 2026 | 13 June 2026 | Direct |  | RT from 994 |
| 7 June 2026 | 14 June 2026 | 1 Stop | | RT from 559 |
| 8 June 2026 | 12 July 2026 | 1 Stop | | RT from 515 |
| 11 June 2026 | 12 June 2026 | 1 Stop | | RT from 553 |
| 16 June 2026 | 18 June 2026 | 1 Stop | | RT from 500 |
| 17 June 2026 | 20 June 2026 | Direct |  | RT from 626 |
| 9 July 2026 | 13 July 2026 | 1 Stop | | RT from 306 |
| 15 July 2026 | 19 July 2026 | Direct | | RT from 449 |
| 29 July 2026 | 3 August 2026 | 1 Stop | | RT from 323 |
| 4 September 2026 | 6 September 2026 | 1 Stop | | RT from 407 |
The Cheapest Flights from San Jose to Chicago for the Year Ahead
| Departure at | Return at | Stops | Airline | Find tickets |
|---|---|---|---|---|
| 16 June 2026 | 18 June 2026 | 1 Stop | | RT from 500 |
| 9 July 2026 | 13 July 2026 | 1 Stop | | RT from 306 |
| 4 September 2026 | 6 September 2026 | 1 Stop | | RT from 407 |