Flight Routes from Chicago to Portland

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

Trip type
Cheapest roundtrip flight
from€436
Fastest outbound flight
Fastest inbound flight
non-stop flights
17x / week
Flight distance
1,426 km
Time difference
Airports in Chicago
  1. O'Hare International Airport, IL
  2. Midway International Airport, IL
  3. Rockford, IL

Flight schedule from Chicago (CHI) to Portland (PWM)

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

offers
Active filtersnone
Matching outbound flightsCHI–PWM · 15 of 15
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. ORDPWM
      nonstop
      1. United Airlines
    2. ORDPWM
      nonstop
      1. American Airlines
    3. ORDPWM
      nonstop
      1. American Airlines
    4. ORDPWM
      nonstop
      1. United Airlines
    5. ORDPWM
      nonstop
      1. American Airlines
    6. ORDPWM
      nonstop
      1. American Airlines
    7. ORDPWM
      nonstop
      1. United Airlines
    8. MDWPWM
      nonstop
      1. Southwest Airlines
    9. ORDPWM
      nonstop
      1. United Airlines
    10. MDWPWM
      nonstop
      1. Southwest Airlines
    11. ORDPWM
      nonstop
      1. United Airlines
    12. ORDPWM
      nonstop
      1. American Airlines
    13. MDWPWM
      nonstop
      1. Southwest Airlines
    14. MDWPWM
      nonstop
      1. Southwest Airlines
    15. ORDPWM
      nonstop
      1. American Airlines

      Important flight information

      Discover more flights around Chicago and Portland

      Departure airport Airport Chicago-IL, all airports (CHI)
      Arrival airport Airport Portland, ME (PWM)
      Destination country Flights to United States
      Departure airport - Destination country Chicago-IL, all airports - United States
      Alternative routes to United States
      Alternative flights to Portland
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