Chicago to San Diego

MDWSAN

Fly from Chicago to San Diego starting at USD 131 with Southwest Airlines.Best fare available on Jun 9, 2026.Limited seats. Better plans. Book before it's gone.

Chicago to San Diego cheapest flights this week

3 Jun
Southwest Airlines
17:15MDW
21:35SAN
Direct$147VIEW DEAL
7 Jun
Southwest Airlines
05:00MDW
14:10SAN
1 Stop$203VIEW DEAL
8 Jun
Southwest Airlines
05:45MDW
09:50SAN
Direct$190VIEW DEAL
9 Jun
Southwest Airlines
06:00MDW
10:10SAN
Direct$131VIEW DEAL
10 Jul
Southwest Airlines
14:15MDW
18:25SAN
Direct$146VIEW DEAL
20 Jul
Southwest Airlines
14:10MDW
23:05SAN
1 Stop$207VIEW DEAL
24 Jul
Southwest Airlines
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

Flights from Chicago

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