San Diego to Chicago
SANMDW
Fly from San Diego to Chicago starting at SAR 491 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
03:22MDW
1 StopSAR 491VIEW DEAL
25 Apr
F9
07:15SAN
03:14MDW
2 StopSAR 758VIEW DEAL
26 Apr
F9
07:20SAN
03:18MDW
1 StopSAR 926VIEW DEAL
27 Apr
F9
21:00SAN
00:31MDW
2 StopSAR 623VIEW DEAL
29 Jun
F9
16:17SAN
16:12MDW
2 StopSAR 840VIEW DEAL
16 Jul
WN
22:40SAN
09:40MDW
DirectSAR 675VIEW DEAL
3 Sept
WN
22:40SAN
09:30MDW
DirectSAR 705VIEW DEAL
San Diego to Chicago monthly flight fare trend
Apr
from SAR 491
May
No flights
Jun
from SAR 840
Jul
from SAR 675
Aug
No flights
Sep
from SAR 705
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
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