Cheap flights from San Francisco to Chicago (All Airports)
San Francisco to Chicago (All Airports) (SFO → CHI). We are tracking 19 fares on this route.
Cheapest tracked fare $129 · typical price $245 · you save about $116 (47%)
Cheapest fares we're tracking
Airline
Departs
Stops
Price
United
2026-09-21
Direct
$129
American
2026-09-28
Direct
$129
American
2026-10-05
Direct
$129
American
2026-10-19
Direct
$129
American
2026-10-26
Direct
$129
American
2026-11-02
Direct
$129
American
2026-11-09
Direct
$129
American
2026-11-16
Direct
$129
American
2026-11-23
Direct
$129
American
2026-09-20
Direct
$169
American
2026-09-27
Direct
$169
American
2026-10-04
Direct
$169
American
2026-10-11
Direct
$169
American
2026-10-12
Direct
$169
American
2026-10-18
Direct
$169
American
2026-10-25
Direct
$169
American
2026-11-01
Direct
$169
American
2026-11-08
Direct
$169
American
2026-11-15
Direct
$169
Could you save more?
The airport you were going to fly from is often not the cheapest one. Compare every airport in a region against each other, or check whether a multi-day stopover beats the direct fare.
How cheap can flights from San Francisco to Chicago (All Airports) get?
The cheapest fare we have tracked on this route is $129, compared with a typical $245 for a trip of this distance.
Is it cheaper to fly to Chicago (All Airports) from a different airport?
Often, yes. Fares out of secondary airports are frequently cheaper than the obvious hub, but they are the ones most likely to be missing from a normal search. Our reverse search compares every airport in a region against each other so the cheaper departure point is not hidden.
Could a stopover make San Francisco to Chicago (All Airports) cheaper?
Sometimes. On thin long-haul routes a two-leg trip with a multi-day stopover can beat the direct fare, and occasionally a direct fare is not sold at all. Our detour search prices those routings against the direct flight.