Flight Routes from Portland to Chicago O'Hare

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

Trip type
Cheapest roundtrip flight
from€429
Flight distance
1,446 km
Time difference

Cheap flight offers from Portland-ME to Chicago O'Hare

sorted by price and recency
filters
  1. –
    American Airlines
    –
    PWM–ORD
    1 stopover
    American Airlines
    –
    ORD–PWM
    1 stopover
    €3,013
  2. –
    American Airlines
    –
    PWM–ORD
    1 stopover
    American Airlines
    –
    ORD–PWM
    1 stopover
    €574
  3. –
    United Airlines
    –
    PWM–ORD
    non-stop flight
    United Airlines
    –
    ORD–PWM
    non-stop flight
    €478
  4. –
    American Airlines
    –
    PWM–ORD
    1 stopover
    American Airlines
    –
    ORD–PWM
    1 stopover
    €429

Flight schedule from Portland (PWM) to Chicago O'Hare (ORD)

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

offers
Active filtersnone
Matching outbound flightsPWM–ORD · 11 of 11
fromto
dep.arr.
durationstopovers
  1. November 8 – 14, 2026
  2. November 15 – 21, 2026
  3. November 22 – 28, 2026
    1. PWMORD
      nonstop
      1. United Airlines
    2. PWMORD
      nonstop
      1. United Airlines
    3. PWMORD
      nonstop
      1. United Airlines
    4. PWMORD
      nonstop
      1. American Airlines
    5. PWMORD
      nonstop
      1. American Airlines
    6. PWMORD
      nonstop
      1. American Airlines
    7. PWMORD
      nonstop
      1. American Airlines
    8. PWMORD
      nonstop
      1. American Airlines
    9. PWMORD
      nonstop
      1. American Airlines
    10. PWMORD
      nonstop
      1. United Airlines
    11. PWMORD
      nonstop
      1. American Airlines

      Important flight information

      Discover more flights around Portland and Chicago O'Hare

      Departure airport Airport Portland, ME (PWM)
      Arrival airport Airport Chicago O'Hare International Airport, IL (ORD)
      Destination country Flights to United States
      Departure airport - Destination country Portland, ME - United States
      Departure airport - City-Code Portland, ME - Chicago
      Alternative routes to United States
      Alternative flights to Chicago O'Hare
      Flight destinations with a similar price
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