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

Cheap flight offers from Chicago to Portland-ME

sorted by price and recency
filters
  1. –
    American Airlines
    –
    CHI–PWM
    non-stop flight
    American Airlines
    –
    PWM–CHI
    non-stop flight
    €581
  2. –
    United Airlines
    –
    CHI–PWM
    non-stop flight
    United Airlines
    –
    PWM–CHI
    non-stop flight
    €501
  3. –
    United Airlines
    –
    CHI–PWM
    non-stop flight
    United Airlines
    –
    PWM–CHI
    non-stop flight
    €491
  4. –
    Delta Air Lines
    –
    CHI–PWM
    1 stopover
    Delta Air Lines
    –
    PWM–CHI
    1 stopover
    €444
  5. –
    American Airlines
    –
    CHI–PWM
    non-stop flight
    American Airlines
    –
    PWM–CHI
    non-stop flight
    €436
  6. –
    American Airlines
    –
    CHI–PWM
    non-stop flight
    American Airlines
    –
    PWM–CHI
    non-stop flight
    €3,015

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 · 12 of 12
fromto
dep.arr.
durationstopovers
  1. November 8 – 14, 2026
  2. November 15 – 21, 2026
  3. November 22 – 28, 2026
    1. ORDPWM
      nonstop
      1. American Airlines
    2. ORDPWM
      nonstop
      1. American Airlines
    3. ORDPWM
      nonstop
      1. American Airlines
    4. ORDPWM
      nonstop
      1. American Airlines
    5. ORDPWM
      nonstop
      1. American Airlines
    6. ORDPWM
      nonstop
      1. American Airlines
    7. ORDPWM
      nonstop
      1. United Airlines
    8. ORDPWM
      nonstop
      1. American Airlines
    9. ORDPWM
      nonstop
      1. United Airlines
    10. ORDPWM
      nonstop
      1. United Airlines
    11. ORDPWM
      nonstop
      1. United Airlines
    12. 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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