Cheap flights Chicago — Portland (CHI — PDX)

Good to know - Cheap tickets Chicago — Portland

Cheapest flight found $60
Minimal flight time 3h 43m
Flight distance 2817 km
Most popular airline American Airlines

Airfare Chicago – Portland by month

Here you can find out in what months how much a ticket Chicago – Portland costs to buy cheap plane tickets.

Month One-way Round-trip
June 2026
March 2026
October 2025
September 2025
August 2025
July 2025
June 2025
May 2025
April 2025
March 2025
February 2025
January 2025

Remember that the optimal time for booking air tickets is 59 days before the departure date, this is the average time at which air tickets were sold at the lowest prices.

Schedule of direct flights Chicago — Portland

Departure Arrival Flight days Flight Airlines Flight time Airports
02:36 04:44 tue 5X970 UPS 4h 8m Chicago Rockford International Airport — Portland International Airport Select dates
02:36 04:19 wed 5X970 UPS 3h 43m Chicago Rockford International Airport — Portland International Airport Select dates
02:36 04:25 tue, wed, thu, fri 5X970 UPS 3h 49m Chicago Rockford International Airport — Portland International Airport Select dates
07:00 09:25 daily AS413 Alaska Airlines 4h 25m O'Hare International Airport — Portland International Airport Select dates
07:10 09:42 mon, thu, fri, sat, sun UA1100 United Airlines 4h 32m O'Hare International Airport — Portland International Airport Select dates
07:25 09:51 mon, wed, thu, sun AA3320 American Airlines 4h 26m O'Hare International Airport — Portland International Airport Select dates
07:25 09:49 mon, tue, fri, sat AA3320 American Airlines 4h 24m O'Hare International Airport — Portland International Airport Select dates
07:45 10:05 sat WN2121 Southwest Airlines 4h 20m Chicago Midway International Airport — Portland International Airport Select dates
07:50 10:10 tue, wed WN2121 Southwest Airlines 4h 20m Chicago Midway International Airport — Portland International Airport Select dates
08:15 10:35 sun WN2121 Southwest Airlines 4h 20m Chicago Midway International Airport — Portland International Airport Select dates
All routes

Flights Chicago — Portland

The selection of cheap flights Chicago — Portland

Here you can find and purchase the cheapest flights Chicago — Portland from $60 and Chicago — Portland — Chicago from $69.

The price of the flight Chicago — Portland (United States) — Chicago from $69 (round-trip).

The average price of the flight Chicago — Portland (United States) — Chicago $384 (round-trip).

Low cost flights Chicago — Portland (CHI — PDX)

The distance between Chicago and Portland 1750 miles (or 2817 kilometres).

The time difference between Chicago and Portland is 2 h.

Minimal flight time from Chicago to Portland 3h 43m.

LowCostClub always do a comparison of airfares Chicago — Portland with several airlines (include UPS, Alaska Airlines, United Airlines). They will always give you all available options so you can find the cheapest flight to Portland. In addition, you can choose the platform where you want to place your orders. There are also special offers for air tickets Chicago — Portland. Last week, for instance, the cheapest round-trip prices stood at $69 while the cheapest one-way price that was available within the last week cost $60

Routes from nearby cities to Portland

A flight from a neighbouring city can help you save money on plane tickets.

The most frequent flight to Portland is from Milwaukee. The cheapest airfare can be purchased with a flight from Grand Rapids from $158. The nearest airports from Chicago with a flight to Portland are in Madison.

Popular International routes from Chicago

Chicago — Perm

Chicago — Pereira

Chicago — Penang

Popular routes from Portland

If you are going to fly from Portland, then study the popular flights. The most popular flights from Portland:

Popular domestic routes from Chicago

FAQ about Chicago — Portland

Yes, they do: 5X970, AS413, UA1100, AA3320, WN2121, UA2254, WN3874, AA1257, AA2545, UA1830, UA2616, AS325, 5X2994, WN1766, WN3698, WN1656, UA580, UA2059, AA2977

Yes, you can fly from Chicago to Portland. Chicago has 8 airports (Merrill C Meigs, DuPage Airport, Chicago Midway International Airport, Chicago NAS, Chicago Executive Airport, Chicago FSS, Chicago Rockford International Airport, O'Hare International Airport) for flights. UPS, Alaska Airlines, United Airlines, American Airlines, Southwest Airlines depart from Chicago on mon, tue, wed, thu, fri, sat, sun. There are non-direct flights through Air Canada, Air Transport International, Allegiant Air, Amazon Air, British Airways, Cathay Pacific, CMA CGM Air Cargo, Delta Air Lines, FedEx, Frontier (Fran the Sea Lion Livery), Icelandair, Jet Linx Aviation, JetBlue, Kalitta Charters, KLM, NetJets, SkyWest Airlines, Southern Airways Express, Spirit Airlines, Sun Country Airlines, Volaris, WestJet.

A direct flight lasts an average of 3h 43m, during which time the aircraft covers a distance of 2817 km.

The price of flights Chicago — Portland starts from $60.

Planes fly Chicago — Portland 7 times a week on the following days: mon, tue, wed, thu, fri, sat, sun

In Chicago — Merrill C Meigs, DuPage Airport, Chicago Midway International Airport, Chicago NAS, Chicago Executive Airport, Chicago FSS, Chicago Rockford International Airport, O'Hare International Airport. In Portland — Portland International Airport.

The following flights fly between Chicago and Portland: 5X970, 5X970, 5X970, AS413, UA1100, AA3320, AA3320, WN2121, WN2121, WN2121, UA2254, WN3874, AA1257, AA2545, AA1257, UA1830, UA2616, UA2616, AS325, AS325, 5X2994, AS325, WN1766, WN3698, WN3698, WN1656, UA580, UA2059, AA2977, WN1766, WN1656, WN3874, WN1656, WN1656

High season is considered to be and the cheapest month is . Enter your preferred airports (or cities) and dates into the search form above to unlock the latest Chicago — Portland flight deals.

The following airlines have direct flights Chicago — Portland: UPS, Alaska Airlines, United Airlines, American Airlines, Southwest Airlines.

All the following airlines flights Chicago — Portland: Air Canada, Air Transport International, Alaska Airlines, Allegiant Air, Amazon Air, American Airlines, British Airways, Cathay Pacific, CMA CGM Air Cargo, Delta Air Lines, FedEx, Frontier (Fran the Sea Lion Livery), Icelandair, Jet Linx Aviation, JetBlue, Kalitta Charters, KLM, NetJets, SkyWest Airlines, Southern Airways Express, Southwest Airlines, Spirit Airlines, Sun Country Airlines, United Airlines, UPS, Volaris, WestJet.

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