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

30 Sept
Southwest Airlines
15:15SAN
20:55MDW
1 StopUSD 181VIEW DEAL
2 Oct
Southwest Airlines
18:45SAN
22:35MDW
DirectUSD 215VIEW DEAL
3 Oct
Southwest Airlines
06:30SAN
10:20MDW
DirectUSD 134VIEW DEAL
3 Oct
Southwest Airlines
22:40SAN
02:30MDW
DirectUSD 174VIEW DEAL
4 Oct
Southwest Airlines
22:40SAN
02:30MDW
DirectUSD 178VIEW DEAL
9 Oct
Southwest Airlines
18:45SAN
22:40MDW
DirectUSD 216VIEW DEAL
23 Oct
Southwest Airlines
22:40SAN
02:30MDW
DirectUSD 161VIEW DEAL
23 Oct
Southwest Airlines
18:45SAN
22:40MDW
DirectUSD 154VIEW DEAL
24 Oct
Southwest Airlines
22:40SAN
02:30MDW
DirectUSD 123VIEW DEAL
24 Oct
Southwest Airlines
06:30SAN
10:20MDW
DirectUSD 144VIEW DEAL

San Diego to Chicago monthly flight fare trend

Sep
from USD 181
Oct
from USD 123
Nov
from USD 143
Dec
No flights
Jan
from USD 134
Feb
from USD 192

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

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