San Diego to Chicago

SANMDW

Fly from San Diego to Chicago starting at SAR 455 with Southwest Airlines.Best fare available on Oct 24, 2026.Limited seats. Better plans. Book before it's gone.

San Diego to Chicago cheapest flights this week

3 Oct
Southwest Airlines
06:30SAN
10:20MDW
DirectSAR 496VIEW DEAL
3 Oct
Southwest Airlines
22:40SAN
02:30MDW
DirectSAR 644VIEW DEAL
4 Oct
Southwest Airlines
22:40SAN
02:30MDW
DirectSAR 659VIEW DEAL
23 Oct
Southwest Airlines
22:40SAN
02:30MDW
DirectSAR 596VIEW DEAL
24 Oct
Southwest Airlines
22:40SAN
02:30MDW
DirectSAR 455VIEW DEAL
1 Nov
Southwest Airlines
22:40SAN
02:25MDW
DirectSAR 529VIEW DEAL
3 Nov
Southwest Airlines
06:30SAN
10:30MDW
DirectSAR 555VIEW DEAL
2 Jan
Southwest Airlines
20:45SAN
03:00MDW
1 StopSAR 1,151VIEW DEAL
11 Jan
Southwest Airlines
06:40SAN
10:35MDW
DirectSAR 514VIEW DEAL
18 Jan
Southwest Airlines
22:40SAN
02:30MDW
DirectSAR 496VIEW DEAL

San Diego to Chicago monthly flight fare trend

Sep
No flights
Oct
from SAR 455
Nov
from SAR 529
Dec
No flights
Jan
from SAR 496
Feb
from SAR 710

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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