San Antonio (SAT) to Chicago (MDW) flights
One airline flies nonstop from San Antonio (SAT) to Chicago (MDW): Southwest Airlines. The two airports are 1,038 miles (1,670 km) apart. There are also 22 ways to fly it with one stop, through Saint Louis, Dallas and Dallas and more.
Airlines flying nonstop from SAT to MDW
- Southwest AirlinesNot in an allianceWho books it
SAT to MDW with one stop
22 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 Dallas (DAL)Southwest Airlines the whole way
- Via Dallas (DFW)American Airlines, then Frontier Airlines
- Via Memphis (MEM)Breeze Airways, then Southwest Airlines
- Via Kansas City (MCI)Southwest Airlines the whole way
- Via Houston (HOU)Southwest Airlines the whole way
- Via Nashville (BNA)Southwest Airlines the whole way
- Via New Orleans (MSY)Southwest Airlines the whole way
- Via Detroit (DTW)Delta Air Lines the whole way
- Via Minneapolis (MSP)Delta Air Lines the whole way
- Via Pensacola (PNS)Breeze Airways, then Southwest Airlines
- Via Atlanta (ATL)Delta Air Lines and Southwest Airlines the whole way
- Via Colorado Springs (COS)Southwest Airlines the whole way
- Via Charlotte (CLT)American Airlines, then Southwest Airlines
- Via Denver (DEN)Southwest Airlines the whole way
SAT to MDW: common questions
Which airlines fly nonstop from SAT to MDW?
Southwest Airlines flies nonstop from San Antonio (SAT) to Chicago (MDW).
How far is San Antonio from Chicago by plane?
San Antonio (SAT) and Chicago (MDW) are 1,038 miles (1,670 km) apart along the great circle, the shortest path a flight can take. Connections add distance on top.
How many miles does SAT 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 SAT to MDW with taxes and fees.
Where can I connect between San Antonio and Chicago?
The most direct connections are through Saint Louis (STL), Dallas (DAL), Dallas (DFW), Memphis (MEM) and Kansas City (MCI). On 16 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.