San Francisco to Chicago

SFOMDW

Fly from San Francisco to Chicago starting at USD 126 with Southwest Airlines.Best fare available on Sep 7, 2026.Limited seats. Better plans. Book before it's gone.

San Francisco to Chicago cheapest flights this week

5 Sept
Frontier Airlines
22:35SFO
08:55MDW
1 StopUSD 191VIEW DEAL
6 Sept
Southwest Airlines
19:25SFO
03:55MDW
1 StopUSD 134VIEW DEAL
6 Sept
Southwest Airlines
10:30SFO
17:55MDW
1 StopUSD 135VIEW DEAL
6 Sept
Frontier Airlines
22:35SFO
08:55MDW
1 StopUSD 139VIEW DEAL
7 Sept
Southwest Airlines
05:35SFO
09:40MDW
DirectUSD 126VIEW DEAL
7 Sept
Southwest Airlines
23:05SFO
08:50MDW
1 StopUSD 139VIEW DEAL
8 Sept
Southwest Airlines
23:40SFO
03:50MDW
DirectUSD 247VIEW DEAL
8 Sept
Frontier Airlines
20:56SFO
15:51MDW
2 StopUSD 155VIEW DEAL
9 Sept
Frontier Airlines
23:58SFO
09:59MDW
1 StopUSD 161VIEW DEAL
9 Sept
Southwest Airlines
13:25SFO
20:55MDW
1 StopUSD 127VIEW DEAL

San Francisco to Chicago monthly flight fare trend

Sep
from USD 98
Oct
from USD 109
Nov
from USD 129
Dec
from USD 204
Jan
from USD 136
Feb
No flights

Airport Details

Origin

San Francisco

San Francisco International Airport (SFO)

San Francisco, SFO
Zone

Los Angeles

Elev

13 ft

Destination

Chicago

Chicago Midway International Airport (MDW)

Chicago, MDW
Zone

Chicago

Elev

620 ft

Flights from San Francisco

Flights from San Francisco to AtlantaFlights from San Francisco to AustinFlights from San Francisco to BostonFlights from San Francisco to CharlotteFlights from San Francisco to DenverFlights from San Francisco to DallasFlights from San Francisco to DetroitFlights from San Francisco to NewarkFlights from San Francisco to Fort LauderdaleFlights from San Francisco to Honolulu