Chicago to San Diego

MDWSAN

Fly from Chicago to San Diego starting at USD 124 with Southwest Airlines.Best fare available on Sep 5, 2026.Limited seats. Better plans. Book before it's gone.

Chicago to San Diego cheapest flights this week

14 Aug
Southwest Airlines
06:15MDW
10:20SAN
DirectUSD 220VIEW DEAL
15 Aug
Southwest Airlines
14:20MDW
20:25SAN
1 StopUSD 159VIEW DEAL
15 Aug
Southwest Airlines
14:05MDW
18:10SAN
DirectUSD 226VIEW DEAL
15 Aug
Southwest Airlines
07:45MDW
15:55SAN
1 StopUSD 201VIEW DEAL
17 Aug
Southwest Airlines
20:45MDW
00:55SAN
DirectUSD 215VIEW DEAL
18 Aug
Southwest Airlines
20:25MDW
00:35SAN
DirectUSD 150VIEW DEAL
20 Aug
Southwest Airlines
20:45MDW
00:55SAN
DirectUSD 126VIEW DEAL
20 Aug
Frontier Airlines
11:50MDW
01:51SAN
3 StopUSD 199VIEW DEAL
2 Sept
Southwest Airlines
15:05MDW
19:10SAN
DirectUSD 147VIEW DEAL
5 Sept
Southwest Airlines
14:05MDW
18:10SAN
DirectUSD 124VIEW DEAL

Chicago to San Diego monthly flight fare trend

Aug
from USD 126
Sep
from USD 100
Oct
from USD 128
Nov
No flights
Dec
from USD 179
Jan
No flights

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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