Cheap flights from Portland to Chicago

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

Weekly direct flights

MondaysTuesdaysWednesdaysThursdaysFridaysSaturdaysSundays
Direct flights7656-65
Fly direct with

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

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

United 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
Delta Air LinesDALDLYesOpens 24 days before flight
Closes 1 hours before flight
Alaska AirlinesASAASYesOpens 24 days before flight
Closes 1 hours before flight
United AirlinesUALUAYesNo
Allegiant AirAAYG4NoOpens 24 days before flight
Closes 1 hours before flight
Frontier AirlinesFFTF9NoOpens 24 days before flight
Closes 1 hours before flight

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 3.9 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, United Airlines, Alaska Airlines.
What are the most popular routes to and from Portland?
Travelers frequently search for route combinations, such as Portland and Denver, Las Vegas, Mexico City, Phoenix, Atlanta, Paris, Los Angeles, Barcelona, San Francisco, Houston, Guadalajara, London, Minneapolis, Washington, D.C., San Diego, Austin, Orlando, Cincinnati, Fort Lauderdale, New Orleans.
What are the most popular routes to and from Chicago?
Travelers frequently search for route combinations, such as Chicago and Phoenix, Las Vegas, Denver, Orlando, San Francisco, Los Angeles, Tampa, Miami, Salt Lake City, New York, Atlanta, London, Sacramento, Minneapolis, Mexico City, Paris, Austin, Washington, D.C., Fort Lauderdale, Fort Myers.
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, Boeing Field, Kenmore Air Harbor Seaplane Base.
What airports are near Chicago?
The main airport in Chicago is O Hare International. It is also served by General Mitchell International, Gerald R. Ford International, Dane County Regional, Central Illinois Regional, General Wayne A. Downing Peoria International, Quad City International, South Bend International, Fort Wayne International, Decatur, Kalamazoo/Battle Creek International.
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.
What is Virtual Interlining and how do I use it?
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How many airports are there near Chicago?
Is it possible to reach Portland by bus or train?
What time do nonstop (direct) flights between Portland and Chicago depart?
What time do nonstop (direct) flights between Portland and Chicago arrive?
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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