Chicago (MDW) to San Antonio (SAT) flights
One airline flies nonstop from Chicago (MDW) to San Antonio (SAT): 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 MDW to SAT
- Southwest AirlinesNot in an allianceWho books it
MDW to SAT 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)Frontier Airlines, then American Airlines
- Via Memphis (MEM)Southwest Airlines, then Breeze Airways
- 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)Southwest Airlines, then Breeze Airways
- Via Atlanta (ATL)Delta Air Lines and Southwest Airlines the whole way
- Via Colorado Springs (COS)Southwest Airlines the whole way
- Via Charlotte (CLT)Southwest Airlines, then American Airlines
- Via Denver (DEN)Southwest Airlines the whole way
MDW to SAT: common questions
Which airlines fly nonstop from MDW to SAT?
Southwest Airlines flies nonstop from Chicago (MDW) to San Antonio (SAT).
How far is Chicago from San Antonio by plane?
Chicago (MDW) and San Antonio (SAT) 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 MDW to SAT 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 SAT with taxes and fees.
Where can I connect between Chicago and San Antonio?
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.