Philadelphia (PHL) to Chicago (MDW) flights
One airline flies nonstop from Philadelphia (PHL) to Chicago (MDW): Southwest Airlines. The two airports are 666 miles (1,072 km) apart. There are also 37 ways to fly it with one stop, through Pittsburgh, Cleveland and Detroit and more.
Airlines flying nonstop from PHL to MDW
- Southwest AirlinesNot in an allianceWho books it
PHL to MDW with one stop
37 connections, most direct first. 2-stop routings and flight times are in Routes with Pro.
- Via Pittsburgh (PIT)American Airlines, then Southwest Airlines
- Via Cleveland (CLE)American Airlines, then Southwest Airlines
- Via Detroit (DTW)Delta Air Lines the whole way
- Via Columbus (CMH)American Airlines, then Southwest Airlines
- Via Baltimore (BWI)Southwest Airlines the whole way
- Via Grand Rapids (GRR)American Airlines and Allegiant Air, then Southwest Airlines
- Via Washington (DCA)American Airlines, then Southwest Airlines
- Via Buffalo (BUF)American Airlines, then Southwest Airlines
- Via Indianapolis (IND)American Airlines, then Southwest Airlines
- Via Cincinnati (CVG)American Airlines, then Southwest Airlines
- Via Milwaukee (MKE)American Airlines, then Southwest Airlines
- Via Rochester (ROC)American Airlines, then Southwest Airlines
- Via Richmond (RIC)American Airlines, then Southwest Airlines
- Via Louisville (SDF)American Airlines, then Southwest Airlines
- Via Norfolk (ORF)American Airlines, then Southwest Airlines
PHL to MDW: common questions
Which airlines fly nonstop from PHL to MDW?
Southwest Airlines flies nonstop from Philadelphia (PHL) to Chicago (MDW).
How far is Philadelphia from Chicago by plane?
Philadelphia (PHL) and Chicago (MDW) are 666 miles (1,072 km) apart along the great circle, the shortest path a flight can take. Connections add distance on top.
How many miles does PHL 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 PHL to MDW with taxes and fees.
Where can I connect between Philadelphia and Chicago?
The most direct connections are through Pittsburgh (PIT), Cleveland (CLE), Detroit (DTW), Columbus (CMH) 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.