Flight Routes from Pittsburgh to Chicago Midway

Compare cheap outbound and return flights from Pittsburgh (PIT) to Chicago Midway (MDW) and find the best offer from numerous airlines and travel agencies.

Trip type
Fastest flight
non-stop flights
40x / week
Flight distance
646 km
Time difference

Flight schedule from Pittsburgh (PIT) to Chicago Midway (MDW)

Select a travel date in the flight schedule for the route from Pittsburgh (PIT) to Chicago Midway (MDW) and compare affordable flight deals.

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Matching outbound flightsPIT–MDW · 16 of 16
fromto
dep.arr.
durationstopovers
  1. September 20 – 26, 2026
  2. Sep 27 – Oct 3, 2026
  3. October 4 – 10, 2026
    1. PITMDW
      nonstop
      1. Southwest Airlines
    2. PITMDW
      nonstop
      1. Southwest Airlines
    3. PITMDW
      nonstop
      1. Southwest Airlines
    4. PITMDW
      nonstop
      1. Southwest Airlines
    5. PITMDW
      nonstop
      1. Southwest Airlines
    6. PITMDW
      nonstop
      1. Southwest Airlines
    7. PITMDW
      nonstop
      1. Southwest Airlines
    8. PITMDW
      nonstop
      1. Southwest Airlines
    9. PITMDW
      nonstop
      1. Southwest Airlines
    10. PITMDW
      nonstop
      1. Southwest Airlines
    11. PITMDW
      nonstop
      1. Southwest Airlines
    12. PITMDW
      nonstop
      1. Southwest Airlines
    13. PITMDW
      nonstop
      1. Southwest Airlines
    14. PITMDW
      nonstop
      1. Southwest Airlines
    15. PITMDW
      nonstop
      1. Southwest Airlines

      Important flight information

      Discover more flights around Pittsburgh and Chicago Midway

      Departure airport Airport Pittsburgh International Airport, PA (PIT)
      Arrival airport Airport Chicago Midway International Airport, IL (MDW)
      Destination country Flights to United States
      Departure airport - Destination country Pittsburgh International Airport, PA - United States
      Departure airport - City-Code Pittsburgh International Airport, PA - Chicago
      Alternative routes to United States
      Alternative flights to Chicago Midway