Saint Louis (STL) to Chicago (MDW) flights
One airline flies nonstop from Saint Louis (STL) to Chicago (MDW): Southwest Airlines. The two airports are 252 miles (405 km) apart. There are also 11 ways to fly it with one stop, through Milwaukee, Kansas City and Nashville and more.
Airlines flying nonstop from STL to MDW
- Southwest AirlinesNot in an allianceWho books it
STL to MDW with one stop
11 connections, most direct first. 2-stop routings and flight times are in Routes with Pro.
- Via Milwaukee (MKE)Southwest Airlines the whole way
- Via Kansas City (MCI)Southwest Airlines the whole way
- Via Nashville (BNA)Southwest Airlines the whole way
- Via Detroit (DTW)Delta Air Lines and Southwest Airlines the whole way
- Via Columbus (CMH)Southwest Airlines the whole way
- Via Omaha (OMA)Southwest Airlines the whole way
- Via Cleveland (CLE)Southwest Airlines the whole way
- Via Minneapolis (MSP)Delta Air Lines and Southwest Airlines the whole way
- Via Pittsburgh (PIT)Southwest Airlines the whole way
- Via Atlanta (ATL)Delta Air Lines, Southwest Airlines and 1 more the whole way
- Via Charlotte (CLT)Southwest Airlines the whole way
STL to MDW: common questions
Which airlines fly nonstop from STL to MDW?
Southwest Airlines flies nonstop from Saint Louis (STL) to Chicago (MDW).
How far is Saint Louis from Chicago by plane?
Saint Louis (STL) and Chicago (MDW) are 252 miles (405 km) apart along the great circle, the shortest path a flight can take. Connections add distance on top.
How many miles does STL 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 STL to MDW with taxes and fees.
Where can I connect between Saint Louis and Chicago?
The most direct connections are through Milwaukee (MKE), Kansas City (MCI), Nashville (BNA), Detroit (DTW) and Columbus (CMH). On 11 of them the same airline flies both flights, for example Southwest Airlines through Milwaukee.
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.