Flight Routes from Portland to Chicago Midway

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

Trip type
Fastest outbound flight
Fastest inbound flight
Flight distance
1,439 km
Time difference

Flight schedule from Portland (PWM) to Chicago Midway (MDW)

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

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Matching outbound flightsPWM–MDW · 6 of 6
fromto
dep.arr.
durationstopovers
  1. September 20 – 26, 2026
  2. Sep 27 – Oct 3, 2026
  3. October 4 – 10, 2026
    1. PWMMDW
      nonstop
      1. Southwest Airlines
    2. PWMMDW
      nonstop
      1. Southwest Airlines
    3. PWMMDW
      nonstop
      1. Southwest Airlines
    4. PWMMDW
      nonstop
      1. Southwest Airlines
    5. PWMMDW
      nonstop
      1. Southwest Airlines
    6. PWMMDW
      nonstop
      1. Southwest Airlines

      Important flight information

      Discover more flights around Portland and Chicago Midway

      Departure airport Airport Portland, ME (PWM)
      Arrival airport Airport Chicago Midway International Airport, IL (MDW)
      Destination country Flights to United States
      Departure airport - Destination country Portland, ME - United States
      Departure airport - City-Code Portland, ME - Chicago
      Alternative flights to Chicago Midway