Cheap flights from San Francisco to Chicago Midway
San Francisco to Chicago Midway (SFO → MDW). We are tracking 6 fares on this route.
Cheapest tracked fare $114 · typical price $245 · you save about $131 (53%)
Cheapest fares we're tracking
Airline
Departs
Stops
Price
Frontier Airlines
2026-10-02
1 stop
$114
—
2026-10-28
Direct
$116
—
2026-11-11
Direct
$116
—
2027-01-06
Direct
$129
—
2027-02-03
Direct
$129
—
2026-11-16
1 stop
$133
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 Midway get?
The cheapest fare we have tracked on this route is $114, compared with a typical $245 for a trip of this distance.
Is it cheaper to fly to Chicago Midway 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 Midway 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.