San Diego to Chicago
SANMDW
Fly from San Diego to Chicago starting at USD 131 with F9.
Best fare available on Apr 23, 2026.
Limited seats. Better plans. Book before it's gone.
San Diego to Chicago cheapest flights this week
23 Apr
F9
07:59SAN
--:--MDW
1 Stop$131VIEW DEAL
25 Apr
F9
07:15SAN
--:--MDW
2 Stop$202VIEW DEAL
26 Apr
F9
07:20SAN
--:--MDW
1 Stop$247VIEW DEAL
27 Apr
F9
21:00SAN
--:--MDW
2 Stop$166VIEW DEAL
29 Jun
F9
16:17SAN
--:--MDW
2 Stop$224VIEW DEAL
16 Jul
WN
22:40SAN
--:--MDW
Direct$180VIEW DEAL
3 Sept
WN
22:40SAN
--:--MDW
Direct$188VIEW DEAL
San Diego to Chicago monthly flight fare trend
Apr
from USD 131
May
No flights
Jun
from USD 224
Jul
from USD 180
Aug
No flights
Sep
from USD 188
Airport Details
Origin
San Diego
San Diego International Airport (SAN)
San Diego, SAN
Zone
Los Angeles
Elev
17 ft
Destination
Chicago
Chicago Midway International Airport (MDW)
Chicago, MDW
Zone
Chicago
Elev
620 ft
