Cheap flights from Portland to Chicago

Choose between Alaska Airlines, United Airlines, or Delta Air Lines to find the best price

Why travel with Kiwi.com?
Best price

100+ million searches a day to find you the best available price.

Unique content

Explore unique options you won’t find anywhere else.

Travel hacks

Discover flight options and prices the airlines don’t want you to see.

Travelers usually depart from Portland International, Portland, OR - Union Station, Portland, OR - Holladay Park, 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 Rockford International, Chicago Union Station, or Chicago Downtown Greyhound Station. The distance between Portland and Chicago is 2794 km. The most popular airlines for this route are Alaska Airlines, United Airlines, Delta Air Lines, and American Airlines. Portland and Chicago have 336 direct flights per week.

Weekly direct flights

MondaysTuesdaysWednesdaysThursdaysFridaysSaturdaysSundays
Number of flights57425653-7355
Fly direct with

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

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
Alaska AirlinesASAASYesOpens 24 days before flight
Closes 1 hours before flight
United AirlinesUALUAYesNo
Delta Air LinesDALDLYesOpens 24 days before flight
Closes 1 hours before flight
American AirlinesAALAAYesNo

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 United Airlines, American Airlines, Alaska 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, 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, Fort Wayne International, General Wayne A. Downing Peoria International, South Bend International, Quad City International, Central Illinois Regional, Kalamazoo/Battle Creek International, University of Illinois Willard.
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?
Which airlines fly between Portland and Chicago?
When's the best time to travel between Portland and Chicago?
What flights operate between Portland and Chicago?
How many airports are there near Portland?
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.

Find the best connection from Portland to Chicago

Search, compare, and book flights, trains, or buses to get there.

Search flights, trains & buses