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

19 Jul
Frontier Airlines
06:35SAN
18:32MDW
1 StopUSD 163VIEW DEAL
21 Jul
Frontier Airlines
06:35SAN
14:51MDW
1 StopUSD 138VIEW DEAL
23 Jul
Southwest Airlines
22:40SAN
02:40MDW
DirectUSD 189VIEW DEAL
15 Aug
Frontier Airlines
16:28SAN
07:51MDW
2 StopUSD 189VIEW DEAL
21 Aug
Southwest Airlines
22:40SAN
02:30MDW
DirectUSD 158VIEW 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
from USD 158
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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