San Diego to Chicago

SANMDW

Fly from San Diego to Chicago starting at USD 123 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

9 Oct
Southwest Airlines
18:45SAN
22:40MDW
DirectUSD 216VIEW DEAL
10 Oct
Southwest Airlines
06:30SAN
10:20MDW
DirectUSD 305VIEW DEAL
20 Oct
Southwest Airlines
22:40SAN
02:30MDW
DirectUSD 159VIEW DEAL
23 Oct
Southwest Airlines
22:40SAN
02:30MDW
DirectUSD 161VIEW DEAL
23 Oct
Southwest Airlines
18:45SAN
22:40MDW
DirectUSD 154VIEW DEAL
23 Oct
Southwest Airlines
11:55SAN
15:45MDW
DirectUSD 256VIEW DEAL
24 Oct
Southwest Airlines
22:40SAN
02:30MDW
DirectUSD 123VIEW DEAL
24 Oct
Southwest Airlines
06:30SAN
10:20MDW
DirectUSD 133VIEW DEAL
1 Nov
Southwest Airlines
22:40SAN
02:25MDW
DirectUSD 143VIEW DEAL
2 Nov
Frontier Airlines
19:33SAN
21:47MDW
3 StopUSD 152VIEW DEAL

San Diego to Chicago monthly flight fare trend

Oct
from USD 123
Nov
from USD 119
Dec
No flights
Jan
from USD 139
Feb
from USD 192
Mar
No flights

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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