Chicago to San Diego

MDWSAN

Fly from Chicago to San Diego starting at USD 100 with Southwest Airlines.Best fare available on Nov 3, 2026.Limited seats. Better plans. Book before it's gone.

Chicago to San Diego cheapest flights this week

12 Oct
Southwest Airlines
21:25MDW
01:50SAN
DirectUSD 173VIEW DEAL
15 Oct
Southwest Airlines
05:25MDW
09:50SAN
DirectUSD 173VIEW DEAL
2 Nov
Southwest Airlines
21:20MDW
01:45SAN
DirectUSD 144VIEW DEAL
2 Nov
Frontier Airlines
06:16MDW
01:57SAN
2 StopUSD 118VIEW DEAL
3 Nov
Southwest Airlines
20:55MDW
01:20SAN
DirectUSD 100VIEW DEAL
6 Nov
Southwest Airlines
21:20MDW
01:50SAN
DirectUSD 175VIEW DEAL
10 Dec
Southwest Airlines
20:55MDW
01:20SAN
DirectUSD 135VIEW DEAL
17 Dec
Southwest Airlines
10:10MDW
14:35SAN
DirectUSD 179VIEW DEAL
18 Dec
Southwest Airlines
21:15MDW
01:50SAN
DirectUSD 218VIEW DEAL
19 Dec
Southwest Airlines
18:20MDW
00:35SAN
1 StopUSD 200VIEW DEAL

Chicago to San Diego monthly flight fare trend

Oct
from USD 173
Nov
from USD 100
Dec
from USD 135
Jan
from USD 118
Feb
from USD 172
Mar
from USD 205

Airport Details

Origin

Chicago

Chicago Midway International Airport (MDW)

Chicago, MDW
Zone

Chicago

Elev

620 ft

Destination

San Diego

San Diego International Airport (SAN)

San Diego, SAN
Zone

Los Angeles

Elev

17 ft

Flights from Chicago

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