Cheap flights Portland — Chicago (PDX — CHI)

Good to know - Cheap tickets Portland — Chicago

Cheapest flight found $73
Minimal flight time 3h 14m
Flight distance 2817 km
Most popular airline Southwest Airlines

Airfare Portland – Chicago by month

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

Month One-way Round-trip
October 2025
September 2025
August 2025
July 2025
June 2025
May 2025
April 2025
March 2025
February 2025
January 2025
December 2024
November 2024

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 Portland — Chicago

Departure Arrival Flight days Flight Airlines Flight time Airports
05:50 11:45 mon, thu, fri WN2735 Southwest Airlines 3h 55m Portland International Airport — Chicago Midway International Airport Select dates
06:05 12:00 tue, wed, sun WN2321 Southwest Airlines 3h 55m Portland International Airport — Chicago Midway International Airport Select dates
06:20 11:34 tue, wed, thu 5X5975 UPS 3h 14m Portland International Airport — Chicago Rockford International Airport Select dates
06:20 11:42 fri, sat 5X5975 UPS 3h 22m Portland International Airport — Chicago Rockford International Airport Select dates
06:20 12:15 sat WN2735 Southwest Airlines 3h 55m Portland International Airport — Chicago Midway International Airport Select dates
06:20 12:29 wed 5X5975 UPS 4h 9m Portland International Airport — Chicago Rockford International Airport Select dates
07:00 13:06 daily UA1693 United Airlines 4h 6m Portland International Airport — O'Hare International Airport Select dates
07:02 13:07 daily AS324 Alaska Horizon 4h 5m Portland International Airport — O'Hare International Airport Select dates
08:30 14:25 mon, thu, fri WN4169 Southwest Airlines 3h 55m Portland International Airport — Chicago Midway International Airport Select dates
08:47 14:25 fri WN4169 Southwest Airlines 3h 38m Portland International Airport — Chicago Midway International Airport Select dates
All routes

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

2025-08-14 one-way

2025-08-11 one-way

2025-08-10 one-way

Flights Portland — Chicago

The selection of cheap flights Portland — Chicago

Here you can find and purchase the cheapest flights Portland — Chicago from $73 and Portland — Chicago — Portland from $34.

The price of the flight Portland — Chicago (United States) — Portland from $34 (round-trip).

The average price of the flight Portland — Chicago (United States) — Portland $396 (round-trip).

Low cost flights Portland — Chicago (PDX — CHI)

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

The time difference between Portland and Chicago is 2 h.

Minimal flight time from Portland to Chicago 3h 14m.

LowCostClub always do a comparison of airfares Portland — Chicago with several airlines (include Southwest Airlines, UPS, United Airlines). They will always give you all available options so you can find the cheapest flight to Chicago. In addition, you can choose the platform where you want to place your orders. There are also special offers for air tickets Portland — Chicago. Last week, for instance, the cheapest round-trip prices stood at $34 while the cheapest one-way price that was available within the last week cost $73

Routes from nearby cities to Chicago

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

The most frequent flight to Chicago is from Pasco. The cheapest airfare can be purchased with a flight from Seattle from $48. The nearest airports from Portland with a flight to Chicago are in Walla Walla.

Popular International routes from Portland

Popular routes from Chicago

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

Popular domestic routes from Portland

FAQ about Portland — Chicago

Yes, they do: WN2735, WN2321, 5X5975, UA1693, AS324, WN4169, AA2515, UA534, UA1335, AA3303, AA1257, WN3186, WN2149, WN2248, WN4170, UA1209, AS376, UA2228, UA3924, AA2977, UA1490

Yes, you can fly from Portland to Chicago. Portland has an airport (Portland International Airport) for flights. Southwest Airlines, UPS, United Airlines, Alaska Horizon, American Airlines depart from Portland on mon, tue, wed, thu, fri, sat, sun. There are non-direct flights through ABX Air, Air Canada Express, Air Transport International, Allegiant Air, British Airways, Cathay Pacific, CMA CGM Air Cargo, Delta Connection, FedEx, Frontier (Piper the White Pelican Livery), Icelandair, Jet Linx Aviation, JetBlue, KLM, NetJets, SkyWest Airlines, Southern Airways Express, Spirit Airlines, Sun Country Airlines, Volaris, WestJet.

A direct flight lasts an average of 3h 14m, during which time the aircraft covers a distance of 2817 km.

The price of flights Portland — Chicago starts from $73.

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

In Portland — Portland International Airport. 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.

The following flights fly between Portland and Chicago: WN2735, WN2321, 5X5975, 5X5975, WN2735, 5X5975, UA1693, AS324, WN4169, WN4169, WN2735, WN4169, AA2515, AA2515, UA534, UA534, UA1335, UA1335, UA1335, AA3303, AA3303, AA1257, WN3186, WN2149, WN2248, WN4170, UA1209, WN4170, AA1257, AS376, UA2228, UA3924, AA2977, UA1490, UA1490

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 Portland — Chicago flight deals.

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

All the following airlines flights Portland — Chicago: ABX Air, Air Canada Express, Air Transport International, Alaska Horizon, Allegiant Air, American Airlines, British Airways, Cathay Pacific, CMA CGM Air Cargo, Delta Connection, FedEx, Frontier (Piper the White Pelican Livery), Icelandair, Jet Linx Aviation, JetBlue, KLM, NetJets, SkyWest Airlines, Southern Airways Express, Southwest Airlines, Spirit Airlines, Sun Country Airlines, United Airlines, UPS, Volaris, WestJet.

Low price calendar

We use cookies and similar technologies for different purposes. Read the privacy policy. If you use the site you agree to them.