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

20 Jul
Southwest Airlines
14:10MDW
23:05SAN
1 StopUSD 207VIEW DEAL
21 Jul
Southwest Airlines
06:10MDW
10:20SAN
DirectUSD 194VIEW DEAL
22 Jul
Southwest Airlines
10:10MDW
19:05SAN
1 StopUSD 247VIEW DEAL
24 Jul
Southwest Airlines
21:10MDW
01:25SAN
DirectUSD 180VIEW DEAL
24 Jul
Southwest Airlines
05:45MDW
09:50SAN
DirectUSD 236VIEW DEAL
30 Jul
Southwest Airlines
05:45MDW
09:50SAN
DirectUSD 194VIEW DEAL
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
2 Aug
Southwest Airlines
06:10MDW
10:20SAN
DirectUSD 244VIEW DEAL

Chicago to San Diego monthly flight fare trend

Jul
from USD 180
Aug
from USD 126
Sep
from USD 167
Oct
from USD 128
Nov
No flights
Dec
from USD 179

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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