San Diego to Chicago

SANMDW

Fly from San Diego to Chicago starting at USD 138 with Frontier Airlines.Best fare available on Jul 21, 2026.Limited seats. Better plans. Book before it's gone.

San Diego to Chicago cheapest flights this week

7 Jul
Frontier Airlines
06:35SAN
14:51MDW
1 StopUSD 139VIEW DEAL
8 Jul
Frontier Airlines
06:35SAN
13:50MDW
1 StopUSD 143VIEW DEAL
15 Jul
Frontier Airlines
06:35SAN
13:50MDW
1 StopUSD 143VIEW DEAL
16 Jul
Southwest Airlines
22:40SAN
02:40MDW
DirectUSD 180VIEW DEAL
17 Jul
Frontier Airlines
06:35SAN
15:22MDW
1 StopUSD 157VIEW DEAL
21 Jul
Frontier Airlines
06:35SAN
14:51MDW
1 StopUSD 138VIEW DEAL
23 Jul
Southwest Airlines
22:40SAN
02:40MDW
DirectUSD 189VIEW DEAL
3 Sept
Southwest Airlines
22:40SAN
02:30MDW
DirectUSD 188VIEW DEAL
1 Nov
Southwest Airlines
22:40SAN
02:25MDW
DirectUSD 143VIEW DEAL
1 Feb
Southwest Airlines
06:40SAN
10:35MDW
DirectUSD 192VIEW DEAL

San Diego to Chicago monthly flight fare trend

Jul
from USD 138
Aug
No flights
Sep
from USD 188
Oct
No flights
Nov
from USD 143
Dec
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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