Cheap Flights from SJC to CHI
The Cheapest Round-trip Tickets from San Jose to Chicago
| Departure at | Return at | Stops | Airline | Find tickets |
|---|---|---|---|---|
| 22 October 2026 | 26 October 2026 | Direct |  | RT from 320 USD |
The Cheapest Flights for this Month from San Jose to Chicago
| Departure at | Return at | Stops | Airline | Find tickets |
|---|---|---|---|---|
| 14 September 2026 | 15 September 2026 | 1 Stop | | RT from 521 USD |
| 22 September 2026 | 24 September 2026 | 1 Stop | | RT from 443 USD |
| 9 October 2026 | 12 October 2026 | 1 Stop |  | RT from 365 USD |
| 22 October 2026 | 26 October 2026 | 1 Stop | | RT from 320 USD |
| 12 November 2026 | 16 November 2026 | 1 Stop | | RT from 333 USD |
| 11 March 2027 | 14 March 2027 | 1 Stop | | RT from 428 USD |
| 12 March 2027 | 15 March 2027 | 1 Stop | | RT from 406 USD |
The Cheapest Flights from San Jose to Chicago for the Year Ahead
| Departure at | Return at | Stops | Airline | Find tickets |
|---|---|---|---|---|
| 22 September 2026 | 24 September 2026 | 1 Stop | | RT from 443 USD |
| 22 October 2026 | 26 October 2026 | 1 Stop | | RT from 320 USD |
| 12 November 2026 | 16 November 2026 | 1 Stop | | RT from 333 USD |
| 12 March 2027 | 15 March 2027 | 1 Stop | | RT from 406 USD |