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Cheap flights from Portland to Chicago

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Cheap return flights

KAYAK's recommended return flight deals from the most popular airlines that fly from Portland to Chicago.
American Airlines Logo
PDX-ORD
3h 56mdirect
American Airlines Logo
ORD-PDX
4h 22mdirect
American Airlines
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Qatar Airways Logo
PDX-ORD
4h 03mdirect
Qatar Airways Logo
ORD-PDX
4h 25mdirect
Qatar Airways
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Air Canada Logo
PDX-ORD
4h 06mdirect
Air Canada Logo
ORD-PDX
4h 32mdirect
Air Canada
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SWISS Logo
PDX-ORD
4h 03mdirect
SWISS Logo
ORD-PDX
4h 32mdirect
United Airlines Logo
PDX-ORD
4h 06mdirect
United Airlines Logo
ORD-PDX
4h 32mdirect
United Airlines
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Alaska Airlines Logo
PDX-ORD
4h 07mdirect
Alaska Airlines Logo
ORD-PDX
4h 25mdirect
Alaska Airlines
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Southwest Logo
PDX-MDW
4h 00mdirect
Southwest Logo
MDW-PDX
4h 20mdirect
Southwest
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Finnair Logo
PDX-ORD
3h 58mdirect
Finnair Logo
ORD-PDX
4h 32mdirect
Finnair
Find Deal
Hawaiian Airlines Logo
PDX-ORD
4h 07mdirect
Hawaiian Airlines Logo
ORD-PDX
4h 25mdirect
Hawaiian Airlines
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Malaysia Airlines Logo
PDX-ORD
4h 03mdirect
Malaysia Airlines Logo
ORD-PDX
4h 32mdirect
Malaysia Airlines
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Brussels Airlines Logo
PDX-ORD
4h 06mdirect
Brussels Airlines Logo
ORD-PDX
4h 32mdirect
Brussels Airlines
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Lufthansa Logo
PDX-ORD
3h 58mdirect
Lufthansa Logo
ORD-PDX
4h 32mdirect
Lufthansa
Find Deal
British Airways Logo
PDX-ORD
4h 03mdirect
British Airways Logo
ORD-PDX
4h 32mdirect
British Airways
Find Deal
Gulf Air Logo
PDX-ORD
4h 03mdirect
Gulf Air Logo
ORD-PDX
4h 28mdirect
Gulf Air
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See travel insights to Chicago from

How to get the cheapest flight ticket from Portland to Chicago

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the cheapest month to fly to Chicago?

The month of January is, on average, the cheapest month to fly to Chicago from Portland, with most prices found around R4 825. If you are unable to visit Chicago during the month of January, then departing from Portland during the month August is also very affordable. Most momondo users find prices during this month for around R5 448.

What is the cheapest Portland to Chicago flight route?

Fly from Portland to Chicago Midway for the best Portland - Chicago flight prices

How far in advance should I book a flight to Chicago?

You are more likely to see cheaper flights to Chicago from Portland when booking 11 weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around R6 573 when searching 11 weeks out.However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago from Portland for as low as R5 357 on momondo.

What cabin class options are available on Portland to Chicago flights?

There are 1 cabin classes available to choose from on Portland to Chicago flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

How have Portland to Chicago flight prices changed over time?

As of April 2025, prices for Portland to Chicago flights are approximately 2% more expensive when compared to flights at the same time last year.

When to book flights from Portland to Chicago

Are you open to changing your travel dates? Check out the ideal times to fly from Portland to Chicago according to our flight data. Find out which month and days have the cheapest flights.
Estimated return price

Cheap Portland to Chicago (PDX to CHI) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Portland to Chicago

Direct flights

None
There are no direct flights from Portland to Chicago. There are no popular flight routes from Portland to Chicago.

  • How far is Portland to Chicago by plane?

    The straight-line distance from Portland to Chicago is 2821,8 km.

  • When did momondo last update prices for flights from Portland Airport to Chicago?

    Prices for flights from Portland Airport to Chicago are updated daily.

  • How old do you have to be to fly from Portland Airport to Chicago?

    The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and stopovers. It is recommended that you verify with the airline you are booking with for travel from Portland Airport to Chicago.

  • What documentation or ID do you need to fly to Chicago?

    The necessary travel and health documents for your Chicago trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's licence and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.

  • What is the most popular plane model from Portland to Chicago?


Why use momondo?

Why should I use momondo to find a flight deal from Portland to Chicago?

We help find the flight that best suits your needs, momondo compares prices from hundreds of airlines and travel agents and helps you filter them to find the best flight from Portland to Chicago for you.

Can I find flights from Portland to Chicago with flexible booking policies on momondo?

Yes. momondo allows you to filter the results for Portland to Chicago flights to just show those with flexible booking policies.

How can momondo help me find flights from Portland to Chicago?

Once you have performed a search in the form on the page, momondo provides useful filters and insights. We can show you the cheapest days and times to fly as well as help filter your options to help you make an informed choice when booking flights to Chicago from Portland.

I’m not ready to book a flight from Portland to Chicago right now. Can momondo alert me if prices change?

Price alerts on flights to Chicago from Portland are quick and easy to set up on momondo. Simply perform a search and select the price alert feature. It is as simple as that.


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Find better results for your trip to the United States

Fly into one of these airports located in Chicago

Airports listed have a maximum distance of 25.6 km from Chicago