Flight Routes from Chicago Midway to Portland

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

Trip type
Fastest flight
non-stop flights
1x / week
Flight distance
1,439 km
Time difference

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

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

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Matching outbound flights4 of 4
fromto
dep.arr.
durationstopovers
  1. September 13 – 19, 2026
  2. September 20 – 26, 2026
  3. Sep 27 – Oct 3, 2026
    1. MDWPWM
      nonstop
      1. Southwest Airlines
    2. MDWPWM
      nonstop
      1. Southwest Airlines
    3. MDWPWM
      nonstop
      1. Southwest Airlines
    4. MDWPWM
      nonstop
      1. Southwest Airlines

      Important flight information

      Discover more flights around Chicago Midway and Portland

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