San Francisco to Chicago
SFOMDW
Fly from San Francisco to Chicago starting at USD 117 with WN.
Best fare available on May 6, 2026.
Limited seats. Better plans. Book before it's gone.
San Francisco to Chicago cheapest flights this week
23 Apr
F9
23:16SFO
--:--MDW
1 Stop$134VIEW DEAL
26 Apr
F9
06:00SFO
--:--MDW
2 Stop$205VIEW DEAL
27 Apr
WN
05:15SFO
--:--MDW
Direct$244VIEW DEAL
6 May
WN
05:25SFO
--:--MDW
Direct$117VIEW DEAL
7 May
F9
23:59SFO
--:--MDW
1 Stop$137VIEW DEAL
8 May
F9
23:59SFO
--:--MDW
1 Stop$138VIEW DEAL
10 May
F9
22:15SFO
--:--MDW
1 Stop$145VIEW DEAL
23 May
WN
23:25SFO
--:--MDW
Direct$130VIEW DEAL
2 Jun
F9
22:15SFO
--:--MDW
1 Stop$128VIEW DEAL
3 Jun
WN
06:20SFO
--:--MDW
1 Stop$180VIEW DEAL
San Francisco to Chicago monthly flight fare trend
Apr
from USD 134
May
from USD 117
Jun
from USD 128
Jul
from USD 155
Aug
from USD 158
Sep
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
