Chicago to San Diego
MDWSAN
Fly from Chicago to San Diego starting at USD 109 with F9.
Best fare available on Apr 27, 2026.
Limited seats. Better plans. Book before it's gone.
Chicago to San Diego cheapest flights this week
20 Apr
F9
16:14MDW
--:--SAN
1 Stop$183VIEW DEAL
23 Apr
F9
16:15MDW
--:--SAN
1 Stop$248VIEW DEAL
27 Apr
F9
13:35MDW
--:--SAN
1 Stop$109VIEW DEAL
4 May
F9
16:14MDW
--:--SAN
1 Stop$140VIEW DEAL
15 May
WN
20:45MDW
--:--SAN
Direct$144VIEW DEAL
3 Jun
WN
17:15MDW
--:--SAN
Direct$147VIEW DEAL
7 Jun
WN
05:00MDW
--:--SAN
1 Stop$203VIEW DEAL
8 Jun
WN
05:45MDW
--:--SAN
Direct$190VIEW DEAL
9 Jun
WN
06:00MDW
--:--SAN
Direct$131VIEW DEAL
10 Jul
WN
14:15MDW
--:--SAN
Direct$146VIEW DEAL
Chicago to San Diego monthly flight fare trend
Apr
from USD 109
May
from USD 140
Jun
from USD 131
Jul
from USD 146
Aug
No flights
Sep
No flights
Airport Details
Origin
Chicago
Chicago Midway International Airport (MDW)
Chicago, MDW
Zone
Chicago
Elev
620 ft
Destination
San Diego
San Diego International Airport (SAN)
San Diego, SAN
Zone
Los Angeles
Elev
17 ft
