Chicago to San Diego

MDWSAN

Fly from Chicago to San Diego starting at USD 177 with Frontier Airlines.Best fare available on Aug 1, 2026.Limited seats. Better plans. Book before it's gone.

Chicago to San Diego cheapest flights this week

1 Aug
Frontier Airlines
06:05MDW
22:06SAN
2 StopUSD 177VIEW DEAL
1 Aug
Southwest Airlines
20:40MDW
01:00SAN
DirectUSD 210VIEW DEAL
1 Aug
Southwest Airlines
10:15MDW
15:30SAN
DirectUSD 234VIEW DEAL
1 Aug
Southwest Airlines
12:50MDW
21:40SAN
1 StopUSD 251VIEW DEAL
2 Aug
Southwest Airlines
06:10MDW
10:20SAN
DirectUSD 279VIEW DEAL
2 Aug
Southwest Airlines
05:25MDW
11:00SAN
1 StopUSD 202VIEW DEAL
5 Aug
Southwest Airlines
08:55MDW
16:15SAN
1 StopUSD 250VIEW DEAL
6 Aug
Southwest Airlines
05:30MDW
11:55SAN
1 StopUSD 271VIEW DEAL
7 Aug
Southwest Airlines
20:45MDW
00:55SAN
DirectUSD 185VIEW DEAL
7 Aug
Southwest Airlines
05:40MDW
11:20SAN
1 StopUSD 258VIEW DEAL

Chicago to San Diego monthly flight fare trend

Aug
from USD 126
Sep
from USD 167
Oct
from USD 128
Nov
No flights
Dec
from USD 179
Jan
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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