San Diego to Chicago
SANMDW
Fly from San Diego to Chicago starting at USD 180 with WN.
Best fare available on Jul 16, 2026.
Limited seats. Better plans. Book before it's gone.
San Diego to Chicago cheapest flights this week
29 Jun
F9
16:17SAN
09:12MDW
2 Stop$224VIEW DEAL
16 Jul
WN
22:40SAN
02:40MDW
Direct$180VIEW DEAL
3 Sept
WN
22:40SAN
02:30MDW
Direct$188VIEW DEAL
San Diego to Chicago monthly flight fare trend
May
No flights
Jun
from USD 224
Jul
from USD 180
Aug
No flights
Sep
from USD 188
Oct
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
Flights from San Diego to AtlantaFlights from San Diego to AustinFlights from San Diego to BostonFlights from San Diego to CharlotteFlights from San Diego to DenverFlights from San Diego to DallasFlights from San Diego to DetroitFlights from San Diego to NewarkFlights from San Diego to Fort LauderdaleFlights from San Diego to Honolulu
