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 Eagle

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
December 2025
October 2025
September 2025
August 2025
July 2025
June 2025
May 2025
April 2025
March 2025
February 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
07:00 09:24 sat AA3320 American Eagle 4h 24m O'Hare International Airport — Portland International Airport Select dates
07:00 09:32 mon, fri, sat AS413 Alaska Airlines 4h 32m O'Hare International Airport — Portland International Airport Select dates
07:00 09:32 thu, fri, sat AS413 AlphaSky 4h 32m O'Hare International Airport — Portland International Airport Select dates
07:09 09:31 daily AA3272 American Eagle 4h 22m O'Hare International Airport — Portland International Airport Select dates
07:10 09:39 sun AA3272 American Eagle 4h 29m O'Hare International Airport — Portland International Airport Select dates
07:15 09:37 mon, thu AA3320 American Eagle 4h 22m O'Hare International Airport — Portland International Airport Select dates
All routes

Sales of tickets from Chicago to Portland in the last 48 hours

2025-10-28 - 2025-11-04

2025-10-28 - 2025-11-04

Dynamics airfare Chicago — Portland by month for the last year

according to LowCost.Club for the last year

The airfare depends on the departure date. Our chart shows the low season prices on route Chicago — Portland

The graph shows that booking flights Chicago — Portland is best planned for October and flights Chicago — Portland — Chicago in the month of October.

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 $57.

The price of the flight Chicago — Portland (United States) — Chicago from $57 (round-trip).

The average price of the flight Chicago — Portland (United States) — Chicago $374 (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, American Eagle). 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 $57 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, AA3320, AA3272, UA1794, WN383, WN1155, WN3735, UA2254, AA2613, UA1830, UA2616, UA1554, AS325, 5X5986, WN3860, WN1656, UA2494, WN3337, UA2059, AA2977, AA3028

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, American Eagle, AlphaSky, United Express, Southwest Airlines depart from Chicago on mon, tue, wed, thu, fri, sat, sun. There are non-direct flights through ABX Air, Air Canada, Air Transport International, Allegiant Air, British Airways, Cathay Pacific, Delta Connection, DHL, FedEx, Frontier (Cali the Mountain Lion Livery), Icelandair, Jet Linx Aviation, KLM, NetJets, Phoenix Air, SkyWest Airlines, Southern Airways Express, Spirit Airlines, Sun Country Airlines, Volaris.

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, AA3320, AS413, AS413, AA3272, AA3272, AA3320, UA1794, AA3320, AA3320, AA3320, AA3320, AA3272, AA3320, WN383, WN1155, WN3735, AA3320, UA2254, AA2613, AA2613, UA1830, UA2616, UA1554, AS325, AS325, AS325, 5X5986, WN3735, WN3860, WN1656, UA2494, WN3337, UA2059, UA2059, UA2059, UA2059, AA2977, WN3735, AA3028, AA2977, AA2977, WN1656, WN3860, AA2977, WN1656, WN1656

High season is considered to be March and the cheapest month is October. 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, American Eagle, AlphaSky, United Express, Southwest Airlines.

All the following airlines flights Chicago — Portland: ABX Air, Air Canada, Air Transport International, Alaska Airlines, Allegiant Air, AlphaSky, American Eagle, British Airways, Cathay Pacific, Delta Connection, DHL, FedEx, Frontier (Cali the Mountain Lion Livery), Icelandair, Jet Linx Aviation, KLM, NetJets, Phoenix Air, SkyWest Airlines, Southern Airways Express, Southwest Airlines, Spirit Airlines, Sun Country Airlines, United Express, UPS, Volaris.

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