Chicago to San Diego
MDWSAN
Fly from Chicago to San Diego starting at USD 131 with WN.
Best fare available on Jun 9, 2026.
Limited seats. Better plans. Book before it's gone.
Chicago to San Diego cheapest flights this week
15 May
WN
20:45MDW
01:10SAN
Direct$144VIEW DEAL
3 Jun
WN
17:15MDW
21:35SAN
Direct$147VIEW DEAL
7 Jun
WN
05:00MDW
14:10SAN
1 Stop$203VIEW DEAL
8 Jun
WN
05:45MDW
09:50SAN
Direct$190VIEW DEAL
9 Jun
WN
06:00MDW
10:10SAN
Direct$131VIEW DEAL
10 Jul
WN
14:15MDW
18:25SAN
Direct$146VIEW DEAL
20 Jul
WN
14:10MDW
23:05SAN
1 Stop$207VIEW DEAL
24 Jul
WN
21:10MDW
01:25SAN
Direct$180VIEW DEAL
Chicago to San Diego monthly flight fare trend
May
from USD 140
Jun
from USD 131
Jul
from USD 146
Aug
No flights
Sep
No flights
Oct
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
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