San Francisco to Chicago
SFOMDW
Fly from San Francisco to Chicago starting at USD 128 with F9.
Best fare available on Jun 2, 2026.
Limited seats. Better plans. Book before it's gone.
San Francisco to Chicago cheapest flights this week
10 May
F9
22:15SFO
09:09MDW
1 Stop$145VIEW DEAL
23 May
WN
23:25SFO
03:40MDW
Direct$130VIEW DEAL
2 Jun
F9
22:15SFO
09:09MDW
1 Stop$128VIEW DEAL
3 Jun
WN
06:20SFO
14:35MDW
1 Stop$180VIEW DEAL
4 Jun
WN
14:15SFO
22:15MDW
1 Stop$161VIEW DEAL
13 Jun
WN
23:40SFO
03:55MDW
Direct$213VIEW DEAL
14 Jun
F9
22:58SFO
13:15MDW
2 Stop$244VIEW DEAL
4 Jul
F9
22:10SFO
09:12MDW
1 Stop$155VIEW DEAL
6 Jul
WN
05:50SFO
10:00MDW
Direct$177VIEW DEAL
5 Aug
F9
23:52SFO
12:07MDW
1 Stop$158VIEW DEAL
San Francisco to Chicago monthly flight fare trend
May
from USD 117
Jun
from USD 128
Jul
from USD 155
Aug
from USD 158
Sep
No flights
Oct
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
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