San Diego to Chicago

SANMDW

Fly from San Diego to Chicago starting at SAR 437 with Southwest Airlines.Best fare available on Sep 9, 2026.Limited seats. Better plans. Book before it's gone.

San Diego to Chicago cheapest flights this week

21 Aug
Southwest Airlines
22:40SAN
02:30MDW
DirectSAR 585VIEW DEAL
21 Aug
Southwest Airlines
06:45SAN
10:45MDW
DirectSAR 636VIEW DEAL
23 Aug
Southwest Airlines
22:40SAN
02:30MDW
DirectSAR 766VIEW DEAL
24 Aug
Southwest Airlines
06:45SAN
10:45MDW
DirectSAR 766VIEW DEAL
25 Aug
Southwest Airlines
22:40SAN
02:30MDW
DirectSAR 655VIEW DEAL
26 Aug
Southwest Airlines
22:40SAN
02:30MDW
DirectSAR 655VIEW DEAL
27 Aug
Southwest Airlines
17:50SAN
21:45MDW
DirectSAR 818VIEW DEAL
29 Aug
Southwest Airlines
22:40SAN
02:30MDW
DirectSAR 659VIEW DEAL
3 Sept
Southwest Airlines
22:40SAN
02:30MDW
DirectSAR 696VIEW DEAL
9 Sept
Southwest Airlines
19:35SAN
03:40MDW
1 StopSAR 437VIEW DEAL

San Diego to Chicago monthly flight fare trend

Aug
from SAR 585
Sep
from SAR 437
Oct
No flights
Nov
from SAR 529
Dec
No flights
Jan
from SAR 511

Airport Details

Origin

San Diego

San Diego International Airport (SAN)

San Diego, SAN
Zone

Los Angeles

Elev

17 ft

Destination

Chicago

Chicago Midway International Airport (MDW)

Chicago, MDW
Zone

Chicago

Elev

620 ft

Flights from San Diego

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