Cheap Flights from SFO to CHI
The Cheapest Round-trip Tickets from San Francisco to Chicago
| Departure at | Return at | Stops | Airline | Find tickets |
|---|---|---|---|---|
| 7 September 2026 | 14 September 2026 | Direct |  | RT from 145 |
The Cheapest Flights for this Month from San Francisco to Chicago
| Departure at | Return at | Stops | Airline | Find tickets |
|---|---|---|---|---|
| 20 July 2026 | 22 July 2026 | 1 Stop |  | RT from 398 |
| 29 July 2026 | 12 August 2026 | 1 Stop | | RT from 307 |
| 30 July 2026 | 11 August 2026 | 1 Stop | | RT from 349 |
| 31 July 2026 | 8 August 2026 | 1 Stop | | RT from 350 |
| 1 August 2026 | 9 August 2026 | 1 Stop | | RT from 383 |
| 2 August 2026 | 7 August 2026 | 1 Stop | | RT from 299 |
| 3 August 2026 | 7 August 2026 | 1 Stop | | RT from 311 |
| 6 August 2026 | 9 August 2026 | 1 Stop |  | RT from 373 |
| 27 August 2026 | 30 August 2026 | 1 Stop | | RT from 267 |
| 7 September 2026 | 14 September 2026 | 1 Stop | | RT from 145 |
| 7 October 2026 | 12 October 2026 | 1 Stop | | RT from 223 |
| 5 February 2027 | 11 February 2027 | 1 Stop |  | RT from 338 |
| 26 March 2027 | 29 March 2027 | 1 Stop | | RT from 452 |
| 27 March 2027 | 29 March 2027 | 1 Stop | | RT from 366 |
The Cheapest Flights from San Francisco to Chicago for the Year Ahead
| Departure at | Return at | Stops | Airline | Find tickets |
|---|---|---|---|---|
| 29 July 2026 | 12 August 2026 | 1 Stop | | RT from 307 |
| 27 August 2026 | 30 August 2026 | 1 Stop | | RT from 267 |
| 7 September 2026 | 14 September 2026 | 1 Stop | | RT from 145 |
| 7 October 2026 | 12 October 2026 | 1 Stop | | RT from 223 |
| 5 February 2027 | 11 February 2027 | 1 Stop | | RT from 338 |
| 27 March 2027 | 29 March 2027 | 1 Stop | | RT from 366 |