Chicago to San Diego

MDWSAN

Fly from Chicago to San Diego starting at USD 100 with Frontier Airlines.Best fare available on Sep 14, 2026.Limited seats. Better plans. Book before it's gone.

Chicago to San Diego cheapest flights this week

9 Sept
Southwest Airlines
20:25MDW
00:40SAN
DirectUSD 127VIEW DEAL
10 Sept
Frontier Airlines
12:54MDW
20:00SAN
1 StopUSD 153VIEW DEAL
14 Sept
Frontier Airlines
12:54MDW
20:00SAN
1 StopUSD 100VIEW DEAL
14 Sept
Frontier Airlines
06:25MDW
20:19SAN
2 StopUSD 139VIEW DEAL
15 Sept
Southwest Airlines
20:25MDW
00:40SAN
DirectUSD 177VIEW DEAL
16 Sept
Southwest Airlines
10:30MDW
17:25SAN
1 StopUSD 193VIEW DEAL
1 Oct
Southwest Airlines
14:55MDW
19:15SAN
DirectUSD 128VIEW DEAL
3 Oct
Southwest Airlines
19:05MDW
23:25SAN
DirectUSD 143VIEW DEAL
12 Oct
Southwest Airlines
21:25MDW
01:50SAN
DirectUSD 173VIEW DEAL
17 Dec
Southwest Airlines
10:10MDW
14:35SAN
DirectUSD 179VIEW DEAL

Chicago to San Diego monthly flight fare trend

Sep
from USD 100
Oct
from USD 128
Nov
No flights
Dec
from USD 179
Jan
No flights
Feb
from USD 172

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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