Cheap Flights from SJC to CHI
The Cheapest Round-trip Tickets from San Jose to Chicago
| Departure at | Return at | Stops | Airline | Find tickets |
|---|---|---|---|---|
| 24 March 2026 | 26 March 2026 | Direct |  | RT from 314 |
The Cheapest Flights for this Month from San Jose to Chicago
| Departure at | Return at | Stops | Airline | Find tickets |
|---|---|---|---|---|
| 6 March 2026 | 6 March 2026 | 1 Stop |  | RT from 1 074 |
| 7 March 2026 | 7 March 2026 | Direct |  | RT from 881 |
| 18 March 2026 | 22 March 2026 | 1 Stop | | RT from 354 |
| 23 March 2026 | 26 March 2026 | 1 Stop | | RT from 345 |
| 24 March 2026 | 26 March 2026 | 1 Stop | | RT from 314 |
| 25 March 2026 | 30 March 2026 | Direct | | RT from 321 |
| 8 April 2026 | 11 April 2026 | 1 Stop | | RT from 340 |
| 9 April 2026 | 12 April 2026 | 3 Stops | | RT from 339 |
| 15 April 2026 | 19 April 2026 | Direct | | RT from 333 |
The Cheapest Flights from San Jose to Chicago for the Year Ahead
| Departure at | Return at | Stops | Airline | Find tickets |
|---|---|---|---|---|
| 24 March 2026 | 26 March 2026 | 1 Stop | | RT from 314 |
| 15 April 2026 | 19 April 2026 | Direct | | RT from 333 |