Chicago to San Diego

MDWSAN

Fly from Chicago to San Diego starting at SAR 474 with Southwest Airlines.Best fare available on Oct 1, 2026.Limited seats. Better plans. Book before it's gone.

Chicago to San Diego cheapest flights this week

16 Sept
Southwest Airlines
10:30MDW
17:25SAN
1 StopSAR 714VIEW DEAL
17 Sept
Frontier Airlines
12:54MDW
20:00SAN
1 StopSAR 759VIEW DEAL
21 Sept
Southwest Airlines
20:45MDW
01:00SAN
DirectSAR 844VIEW DEAL
1 Oct
Southwest Airlines
14:55MDW
19:15SAN
DirectSAR 474VIEW DEAL
3 Oct
Southwest Airlines
19:05MDW
23:25SAN
DirectSAR 529VIEW DEAL
12 Oct
Southwest Airlines
21:25MDW
01:50SAN
DirectSAR 640VIEW DEAL
10 Dec
Southwest Airlines
20:55MDW
01:20SAN
DirectSAR 500VIEW DEAL
17 Dec
Southwest Airlines
10:10MDW
14:35SAN
DirectSAR 662VIEW DEAL
11 Feb
Southwest Airlines
10:00MDW
16:35SAN
1 StopSAR 636VIEW DEAL
11 Mar
Southwest Airlines
22:05MDW
02:35SAN
DirectSAR 759VIEW DEAL

Chicago to San Diego monthly flight fare trend

Sep
from SAR 714
Oct
from SAR 474
Nov
No flights
Dec
from SAR 500
Jan
No flights
Feb
from SAR 636

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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