San Diego to Chicago

SANMDW

Fly from San Diego to Chicago starting at USD 118 with Southwest Airlines.Best fare available on Sep 9, 2026.Limited seats. Better plans. Book before it's gone.

San Diego to Chicago cheapest flights this week

2 Sept
Southwest Airlines
06:55SAN
10:55MDW
DirectUSD 221VIEW DEAL
3 Sept
Southwest Airlines
22:40SAN
02:30MDW
DirectUSD 188VIEW DEAL
6 Sept
Southwest Airlines
22:40SAN
02:30MDW
DirectUSD 313VIEW DEAL
8 Sept
Southwest Airlines
06:55SAN
10:55MDW
DirectUSD 190VIEW DEAL
9 Sept
Southwest Airlines
19:35SAN
03:40MDW
1 StopUSD 118VIEW DEAL
9 Sept
Southwest Airlines
06:55SAN
10:55MDW
DirectUSD 199VIEW DEAL
11 Sept
Southwest Airlines
17:50SAN
21:50MDW
DirectUSD 191VIEW DEAL
16 Sept
Southwest Airlines
22:40SAN
02:30MDW
DirectUSD 200VIEW DEAL
17 Sept
Southwest Airlines
22:25SAN
08:25MDW
1 StopUSD 236VIEW DEAL
18 Sept
Southwest Airlines
22:40SAN
02:30MDW
DirectUSD 211VIEW DEAL

San Diego to Chicago monthly flight fare trend

Sep
from USD 118
Oct
from USD 147
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

Flights from San Diego

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