Pittsburgh (PIT) to Chicago (MDW) flights
One airline flies nonstop from Pittsburgh (PIT) to Chicago (MDW): Southwest Airlines. The two airports are 400 miles (643 km) apart. There are also 17 ways to fly it with one stop, through Detroit, Louisville and Saint Louis and more.
Airlines flying nonstop from PIT to MDW
- Southwest AirlinesNot in an allianceWho books it
PIT to MDW with one stop
17 connections, most direct first. 2-stop routings and flight times are in Routes with Pro.
- Via Detroit (DTW)Delta Air Lines the whole way
- Via Louisville (SDF)Breeze Airways, then Southwest Airlines
- Via Saint Louis (STL)Southwest Airlines the whole way
- Via Washington (DCA)American Airlines, then Southwest Airlines
- Via Baltimore (BWI)Southwest Airlines the whole way
- Via Nashville (BNA)Southwest Airlines the whole way
- Via Philadelphia (PHL)American Airlines, then Southwest Airlines
- Via Charlotte (CLT)American Airlines, then Southwest Airlines
- Via Raleigh/Durham (RDU)American Airlines and Breeze Airways, then Southwest Airlines
- Via Norfolk (ORF)Breeze Airways, then Southwest Airlines
- Via New York (LGA)American Airlines and Delta Air Lines, then Southwest Airlines
- Via Minneapolis (MSP)Delta Air Lines the whole way
- Via Atlanta (ATL)Delta Air Lines and Southwest Airlines the whole way
- Via Hartford (BDL)Breeze Airways, then Southwest Airlines
- Via Myrtle Beach (MYR)Southwest Airlines the whole way
PIT to MDW: common questions
Which airlines fly nonstop from PIT to MDW?
Southwest Airlines flies nonstop from Pittsburgh (PIT) to Chicago (MDW).
How far is Pittsburgh from Chicago by plane?
Pittsburgh (PIT) and Chicago (MDW) are 400 miles (643 km) apart along the great circle, the shortest path a flight can take. Connections add distance on top.
How many miles does PIT 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 PIT to MDW with taxes and fees.
Where can I connect between Pittsburgh and Chicago?
The most direct connections are through Detroit (DTW), Louisville (SDF), Saint Louis (STL), Washington (DCA) and Baltimore (BWI). On 7 of them the same airline flies both flights, for example Delta Air Lines through Detroit.
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.