Cheap Flights from SJC to CHI
The Cheapest Round-trip Tickets from San Jose to Chicago
| Departure at | Return at | Stops | Airline | Find tickets |
|---|---|---|---|---|
| 7 September 2026 | 14 September 2026 | Direct |  | RT from 146 |
The Cheapest Flights for this Month from San Jose to Chicago
| Departure at | Return at | Stops | Airline | Find tickets |
|---|---|---|---|---|
| 20 July 2026 | 22 July 2026 | 2 Stops |  | RT from 573 |
| 31 July 2026 | 8 August 2026 | 1 Stop | | RT from 367 |
| 1 August 2026 | 9 August 2026 | 1 Stop |  | RT from 480 |
| 2 August 2026 | 7 August 2026 | Direct | | RT from 494 |
| 3 August 2026 | 7 August 2026 | 1 Stop | | RT from 403 |
| 6 August 2026 | 9 August 2026 | 1 Stop | | RT from 387 |
| 27 August 2026 | 30 August 2026 | 1 Stop | | RT from 283 |
| 7 September 2026 | 14 September 2026 | 1 Stop | | RT from 146 |
| 7 October 2026 | 12 October 2026 | Direct | | RT from 466 |
| 5 February 2027 | 11 February 2027 | 1 Stop | | RT from 313 |
| 26 March 2027 | 29 March 2027 | 1 Stop | | RT from 366 |
| 27 March 2027 | 29 March 2027 | 1 Stop | | RT from 366 |
The Cheapest Flights from San Jose to Chicago for the Year Ahead
| Departure at | Return at | Stops | Airline | Find tickets |
|---|---|---|---|---|
| 31 July 2026 | 8 August 2026 | 1 Stop | | RT from 367 |
| 27 August 2026 | 30 August 2026 | 1 Stop | | RT from 283 |
| 7 September 2026 | 14 September 2026 | 1 Stop | | RT from 146 |
| 7 October 2026 | 12 October 2026 | Direct | | RT from 466 |
| 5 February 2027 | 11 February 2027 | 1 Stop | | RT from 313 |
| 26 March 2027 | 29 March 2027 | 1 Stop | | RT from 366 |