San Diego (SAN) to Chicago (MDW) flights
One airline flies nonstop from San Diego (SAN) to Chicago (MDW): Southwest Airlines. The two airports are 1,726 miles (2,778 km) apart. There are also 51 ways to fly it with one stop, through Colorado Springs, Omaha and Kansas City and more.
Airlines flying nonstop from SAN to MDW
- Southwest AirlinesNot in an allianceWho books it
SAN to MDW with one stop
51 connections, most direct first. 2-stop routings and flight times are in Routes with Pro.
- Via Colorado Springs (COS)Southwest Airlines the whole way
- Via Omaha (OMA)Southwest Airlines the whole way
- Via Kansas City (MCI)Southwest Airlines the whole way
- Via Phoenix (PHX)Southwest Airlines the whole way
+1
- Via Denver (DEN)Southwest Airlines the whole way
+1 - Via Albuquerque (ABQ)Southwest Airlines the whole way
- Via Las Vegas (LAS)Southwest Airlines the whole way
+1 - Via Tucson (TUS)Southwest Airlines the whole way
- Via Saint Louis (STL)Southwest Airlines the whole way
- Via Milwaukee (MKE)Southwest Airlines the whole way
- Via Tulsa (TUL)Alaska Airlines, then Southwest Airlines
- Via Los Angeles (LAX)Delta Air Lines and United Airlines, then Southwest Airlines
- Via El Paso (ELP)Southwest Airlines the whole way
- Via Minneapolis (MSP)Delta Air Lines the whole way
- Via Salt Lake City (SLC)Southwest Airlines the whole way
SAN to MDW: common questions
Which airlines fly nonstop from SAN to MDW?
Southwest Airlines flies nonstop from San Diego (SAN) to Chicago (MDW).
How far is San Diego from Chicago by plane?
San Diego (SAN) and Chicago (MDW) are 1,726 miles (2,778 km) apart along the great circle, the shortest path a flight can take. Connections add distance on top.
How many miles does SAN to MDW cost?
It depends on the program: each prices the route from its own chart or dynamically. The Award Flight Pricer compares 30+ programs for SAN to MDW with taxes and fees.
Where can I connect between San Diego and Chicago?
The most direct connections are through Colorado Springs (COS), Omaha (OMA), Kansas City (MCI), Phoenix (PHX) and Denver (DEN). On 41 of them the same airline flies both flights, for example Southwest Airlines through Colorado Springs.
More routes
Routes are scheduled nonstop flights. The route data is refreshed monthly; this list was last checked November 11, 2026. Seasonal routes and new launches can be missing or end early, so confirm with the airline before you book. Distances are great-circle, the shortest path between the two airports.