Houston (HOU) to Chicago (MDW) flights
One airline flies nonstop from Houston (HOU) to Chicago (MDW): Southwest Airlines. The two airports are 939 miles (1,511 km) apart. There are also 36 ways to fly it with one stop, through Saint Louis, Memphis and Indianapolis and more.
Airlines flying nonstop from HOU to MDW
- Southwest AirlinesNot in an allianceWho books it
HOU to MDW with one stop
36 connections, most direct first. 2-stop routings and flight times are in Routes with Pro.
- Via Saint Louis (STL)Southwest Airlines the whole way
- Via Memphis (MEM)Southwest Airlines the whole way
- Via Indianapolis (IND)Southwest Airlines the whole way
- Via Dallas (DAL)Southwest Airlines the whole way
- Via Tulsa (TUL)Southwest Airlines the whole way
- Via Dallas (DFW)American Airlines, then Frontier Airlines
- Via Nashville (BNA)Southwest Airlines the whole way
- Via Kansas City (MCI)Southwest Airlines the whole way
- Via Louisville (SDF)Southwest Airlines the whole way
- Via Oklahoma City (OKC)Southwest Airlines the whole way
- Via Austin (AUS)Southwest Airlines the whole way
- Via New Orleans (MSY)Southwest Airlines the whole way
- Via Birmingham (BHM)Southwest Airlines the whole way
- Via Omaha (OMA)Southwest Airlines the whole way
- Via San Antonio (SAT)Southwest Airlines the whole way
HOU to MDW: common questions
Which airlines fly nonstop from HOU to MDW?
Southwest Airlines flies nonstop from Houston (HOU) to Chicago (MDW).
How far is Houston from Chicago by plane?
Houston (HOU) and Chicago (MDW) are 939 miles (1,511 km) apart along the great circle, the shortest path a flight can take. Connections add distance on top.
How many miles does HOU 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 HOU to MDW with taxes and fees.
Where can I connect between Houston and Chicago?
The most direct connections are through Saint Louis (STL), Memphis (MEM), Indianapolis (IND), Dallas (DAL) and Tulsa (TUL). On 33 of them the same airline flies both flights, for example Southwest Airlines through Saint Louis.
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.