Chicago to San Diego

MDWSAN

Fly from Chicago to San Diego starting at SAR 485 with Southwest Airlines.Best fare available on Aug 12, 2026.Limited seats. Better plans. Book before it's gone.

Chicago to San Diego cheapest flights this week

5 Aug
Southwest Airlines
08:55MDW
16:15SAN
1 StopSAR 925VIEW DEAL
6 Aug
Southwest Airlines
05:30MDW
11:55SAN
1 StopSAR 1,003VIEW DEAL
7 Aug
Southwest Airlines
20:45MDW
00:55SAN
DirectSAR 685VIEW DEAL
7 Aug
Southwest Airlines
05:40MDW
11:20SAN
1 StopSAR 955VIEW DEAL
8 Aug
Southwest Airlines
10:10MDW
22:06SAN
2 StopSAR 611VIEW DEAL
9 Aug
Frontier Airlines
06:05MDW
01:51SAN
2 StopSAR 607VIEW DEAL
10 Aug
Southwest Airlines
06:15MDW
10:20SAN
DirectSAR 703VIEW DEAL
10 Aug
Southwest Airlines
18:15MDW
00:10SAN
1 StopSAR 999VIEW DEAL
11 Aug
Southwest Airlines
15:05MDW
19:10SAN
DirectSAR 703VIEW DEAL
12 Aug
Southwest Airlines
06:40MDW
12:35SAN
1 StopSAR 485VIEW DEAL

Chicago to San Diego monthly flight fare trend

Aug
from SAR 466
Sep
from SAR 370
Oct
from SAR 474
Nov
No flights
Dec
from SAR 662
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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