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