San Diego to Chicago

SANMDW

Fly from San Diego to Chicago starting at USD 128 with Southwest Airlines.Best fare available on Aug 18, 2026.Limited seats. Better plans. Book before it's gone.

San Diego to Chicago cheapest flights this week

5 Aug
Frontier Airlines
06:35SAN
13:50MDW
1 StopUSD 139VIEW DEAL
6 Aug
Southwest Airlines
17:50SAN
21:45MDW
DirectUSD 257VIEW DEAL
7 Aug
Frontier Airlines
06:35SAN
15:22MDW
1 StopUSD 209VIEW DEAL
15 Aug
Frontier Airlines
16:28SAN
07:51MDW
2 StopUSD 189VIEW DEAL
18 Aug
Southwest Airlines
22:40SAN
02:30MDW
DirectUSD 128VIEW 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
2 Jan
Southwest Airlines
20:45SAN
03:00MDW
1 StopUSD 311VIEW DEAL
1 Feb
Southwest Airlines
06:40SAN
10:35MDW
DirectUSD 192VIEW DEAL

San Diego to Chicago monthly flight fare trend

Aug
from USD 128
Sep
from USD 188
Oct
No flights
Nov
from USD 143
Dec
No flights
Jan
from USD 311

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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