Chicago to San Diego

MDWSAN

Fly from Chicago to San Diego starting at USD 146 with Southwest Airlines.Best fare available on Jul 10, 2026.Limited seats. Better plans. Book before it's gone.

Chicago to San Diego cheapest flights this week

8 Jul
Southwest Airlines
06:10MDW
10:20SAN
DirectUSD 213VIEW DEAL
10 Jul
Southwest Airlines
14:15MDW
18:25SAN
DirectUSD 146VIEW DEAL
20 Jul
Southwest Airlines
14:10MDW
23:05SAN
1 StopUSD 207VIEW DEAL
21 Jul
Southwest Airlines
06:10MDW
10:20SAN
DirectUSD 194VIEW DEAL
24 Jul
Southwest Airlines
21:10MDW
01:25SAN
DirectUSD 180VIEW DEAL
30 Jul
Southwest Airlines
05:45MDW
09:50SAN
DirectUSD 194VIEW DEAL
1 Aug
Frontier Airlines
06:05MDW
22:06SAN
2 StopUSD 177VIEW DEAL
2 Aug
Southwest Airlines
06:10MDW
10:20SAN
DirectUSD 194VIEW DEAL
7 Aug
Southwest Airlines
20:45MDW
00:55SAN
DirectUSD 185VIEW DEAL
10 Aug
Southwest Airlines
06:15MDW
10:20SAN
DirectUSD 190VIEW DEAL

Chicago to San Diego monthly flight fare trend

Jul
from USD 146
Aug
from USD 177
Sep
from USD 167
Oct
No flights
Nov
No flights
Dec
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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