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
Cheapest roundtrip flight
from€615
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.

offers
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Matching outbound flightsMDW–PWM · 4 of 4
fromto
dep.arr.
durationstopovers
  1. Sep 27 – Oct 3, 2026
  2. October 4 – 10, 2026
  3. October 11 – 17, 2026
    No flights could be found for the active filters.
    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
      Alternative routes to United States
      Alternative flights to Portland
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