Cheap Flights from SFO to CHI
The Cheapest Round-trip Tickets from San Francisco to Chicago
| Departure at | Return at | Stops | Airline | Find tickets |
|---|---|---|---|---|
| 22 May 2026 | 25 May 2026 | Direct |  | RT from 189 |
The Cheapest Flights for this Month from San Francisco to Chicago
| Departure at | Return at | Stops | Airline | Find tickets |
|---|---|---|---|---|
| 8 May 2026 | 11 May 2026 | 1 Stop |  | RT from 319 |
| 15 May 2026 | 17 May 2026 | 3 Stops | | RT from 360 |
| 22 May 2026 | 25 May 2026 | 2 Stops | | RT from 189 |
| 5 June 2026 | 7 June 2026 | 1 Stop | | RT from 289 |
| 12 June 2026 | 16 June 2026 | 1 Stop | | RT from 285 |
| 29 July 2026 | 3 August 2026 | 1 Stop | | RT from 290 |
| 31 July 2026 | 3 August 2026 | 1 Stop | | RT from 309 |
| 18 September 2026 | 27 September 2026 | 1 Stop |  | RT from 327 |
| 23 January 2027 | 29 January 2027 | 1 Stop | | RT from 303 |
The Cheapest Flights from San Francisco to Chicago for the Year Ahead
| Departure at | Return at | Stops | Airline | Find tickets |
|---|---|---|---|---|
| 22 May 2026 | 25 May 2026 | 2 Stops | | RT from 189 |
| 12 June 2026 | 16 June 2026 | 1 Stop | | RT from 285 |
| 29 July 2026 | 3 August 2026 | 1 Stop | | RT from 290 |
| 18 September 2026 | 27 September 2026 | 1 Stop | | RT from 327 |
| 23 January 2027 | 29 January 2027 | 1 Stop | | RT from 303 |