Chicago (MDW) to San Diego (SAN) flights
One airline flies nonstop from Chicago (MDW) to San Diego (SAN): 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 MDW to SAN
- Southwest AirlinesNot in an allianceWho books it
MDW to SAN 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 Denver (DEN)Southwest Airlines the whole way
+1 - Via Phoenix (PHX)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)Southwest Airlines, then Alaska Airlines
- Via Los Angeles (LAX)Southwest Airlines, then Delta Air Lines and United 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
MDW to SAN: common questions
Which airlines fly nonstop from MDW to SAN?
Southwest Airlines flies nonstop from Chicago (MDW) to San Diego (SAN).
How far is Chicago from San Diego by plane?
Chicago (MDW) and San Diego (SAN) 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 MDW to SAN cost?
It depends on the program: each prices the route from its own chart or dynamically. The Award Flight Pricer compares 30+ programs for MDW to SAN with taxes and fees.
Where can I connect between Chicago and San Diego?
The most direct connections are through Colorado Springs (COS), Omaha (OMA), Kansas City (MCI), Denver (DEN) and Phoenix (PHX). 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.