Portland, OR to Chicago, IL flights from £89

Flights starting at £89. Choose between Frontier Airlines, United Airlines, or Spirit Airlines to find the best price.

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Travelers usually depart from Portland International, Portland, OR - Union Station, or Portland, OR - Greyhound Station when they travel from Portland to Chicago. Book your trip to arrive at O Hare International, Chicago Midway International, Chicago, IL - Union Station, Chicago Downtown Greyhound Station, or Chicago Rockford International. The distance between Portland and Chicago is 2794 km. The most popular airlines for this route are Frontier Airlines, United Airlines, Spirit Airlines, Alaska Airlines, and Delta Air Lines. Portland and Chicago have 401 direct flights per week.

Weekly direct flights

MondaysTuesdaysWednesdaysThursdaysFridaysSaturdaysSundays
Direct flights5555555
Fly direct with

American Airlines on Mondays, Tuesdays, Wednesdays, Thursdays, Fridays, Saturdays, and Sundays.

United Airlines on Mondays, Tuesdays, Wednesdays, Thursdays, Fridays, Saturdays, and Sundays.

Alaska Airlines on Mondays, Tuesdays, Wednesdays, Thursdays, Fridays, Saturdays, and Sundays.

Check-in for a flight from Portland to Chicago

NameCarrier codeIATA CodePassport needed during bookingOnline check-in available
Frontier AirlinesFFTF9NoOpens 24 days before flight
Closes 1 hours before flight
United AirlinesUALUAYesNo
Spirit AirlinesNKSNKNoOpens 24 days before flight
Closes 1 hours before flight
Alaska AirlinesASAASYesOpens 24 days before flight
Closes 1 hours before flight
Delta Air LinesDALDLYesOpens 24 days before flight
Closes 1 hours before flight
Learn more about COVID-19 restrictions in United States in our dedicated Stories article.

Frequently asked questions

How long does it take to travel from Portland to Chicago?
A one-way nonstop (direct) flight between Portland and Chicago takes around 4.0 hours.
What is the flight distance between Portland and Chicago?
The flight distance between Portland and Chicago is 2794 km.
What airlines offer nonstop (direct) flights between Portland and Chicago?
Several carriers operate flights between Portland and Chicago. Airlines offering nonstop (direct) flights include American Airlines, Alaska Airlines, United Airlines.
What are the most popular routes to and from Portland?
Travelers frequently search for route combinations, such as Portland and London, San Francisco, Dublin, Phoenix, Washington, D.C., Atlanta, Denver, Las Vegas, Los Angeles, St. Louis, Barcelona, New York, San Diego, Austin, Bangkok, Tallinn, Minneapolis, Santa Ana, Philadelphia, Edinburgh.
What are the most popular routes to and from Chicago?
Travelers frequently search for route combinations, such as Chicago and London, Dublin, Manchester, Toronto, Athens, Orlando, San Francisco, Hyderabad, Vilnius, New York, Las Vegas, Edinburgh, Denver, Bangkok, Minneapolis, Riga, Glasgow, Austin, San Juan, Edmonton.
What airports are near Portland?
The main airport in Portland is Portland International. It is also served by Seattle–Tacoma International, Portland International, Eugene, Roberts Field, Kenmore Air Harbor Seaplane Base, Boeing Field.
What airports are near Chicago?
The main airport in Chicago is O Hare International. It is also served by Gerald R. Ford International, General Mitchell International, Dane County Regional, General Wayne A. Downing Peoria International, South Bend International, Fort Wayne International, Central Illinois Regional, Quad City International, Muskegon County, Decatur.
What buses and trains depart from Portland?
A number of bus and train companies depart from Portland, including Amtrak train.
Is it possible to combine flights, buses, and trains in one itinerary when traveling between Portland and Chicago?
Yes, it's possible to combine different modes of transport between Portland and Chicago thanks to our Virtual Interlining technology. Making use of not only flights but also trains and buses between Portland and Chicago can give rise to new adventures. Read more about how Virtual Interlining works on Kiwi.com Stories.
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What time do flights between Portland and Chicago depart?
What time do flights between Portland and Chicago arrive?

Planning a trip? Thanks to our Virtual Interlining algorithm, we offer billions of route combinations between any A and any B in the world by plane, train, and bus. Find the cheapest routes and best deals for you, as well as the best dates on which to travel.

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