| Outbound | Return | Airlines | Shop | Baggage | Price | ||
|---|---|---|---|---|---|---|---|
| Best option San Francisco Chicago | Outbound 09/19/25 direct AS0598 04h 27min | Return 09/29/25 direct AS0597 04h 50min |  Alaska Airlines |  | ? | $220 | |
| San Francisco Chicago | Outbound 09/19/25 direct AS0598 04h 27min | Return 09/29/25 direct AS0597 04h 50min | Alaska Airlines |  | ? | $230 | |
| San Francisco Chicago | Outbound 09/19/25 direct AS0598 04h 27min | Return 09/29/25 direct AS0597 04h 50min | Alaska Airlines |  | ? | $234 | |
| San Francisco Chicago | Outbound 09/19/25 direct HA7000 04h 27min | Return 09/29/25 direct HA6199 04h 50min |  Hawaiian Airlines |  | $240 | ||
| San Francisco Chicago | Outbound 09/19/25 direct AS0598 04h 27min | Return 09/29/25 direct AS0597 04h 50min | Alaska Airlines |  | ? | $244 | |
| San Francisco Chicago | Outbound 07/25/25 1 Stopover (DEN) F91230, F93174 15h 22min | Return 08/17/25 1 Stopover (DEN) F91483, F93439 20h 39min |  Frontier Airlines |  | $265 | ||
| San Francisco Chicago | Outbound 09/19/25 direct UA2046 04h 19min | Return 09/29/25 direct UA2179 04h 48min |  United Airlines |  | ? | $268 | |
| San Francisco Chicago | Outbound 07/25/25 1 Stopover (DEN) F91230, F93174 15h 22min | Return 08/17/25 1 Stopover (DEN) F91483, F93439 20h 39min | Frontier Airlines |  | $277 | ||
| San Francisco Chicago | Outbound 07/25/25 1 Stopover (LAX) UA2064, UA1843 06h 20min | Return 08/17/25 1 Stopover (LAX) UA2361, UA1791 06h 55min | United Airlines | | ? | $279 | |
| San Francisco Chicago | Outbound 07/25/25 1 Stopover (ATL) F91448, F91441 09h 53min | Return 08/17/25 direct AS0597 04h 48min | Frontier Airlines | | ? | $293 |
Tips and tricks to help you find cheap flights from San Francisco to Chicago
Favorite airline: Frontier Airlines
Most travelers looking for flights on the route from San Francisco to Chicago decide to book flights with Frontier Airlines.
Frontier Airlines
47 %
United Airlines
18 %
Alaska Airlines
17 %