Flights from Chicago to Portland Starting at £57

We've found these cheap flights for you. You can book one-way or return flight tickets.

Round-trip
One way

Crossed out prices are calculated based on the average price of the corresponding route on Trip.com.

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Cheapest flights

From price

16 23
23 30
Apr

30 6
6 13
13 20
20 27
May

27 4
4 11
11 18
18 25
Jun

25 1
1 8

Displayed prices are calculated based on the cheapest average weekly prices of the corresponding route on Trip.com.

FAQ

When are flight tickets from Chicago (CHI) to Portland (PWM) the cheapest?

Airlines adjust prices for flights from Chicago to Portland based on the date and time of your booking. By analyzing data from all airlines, on Trip.com, you can find the cheapest flight prices on Tuesdays, Wednesdays, and Saturdays.
How much are flights from Chicago (CHI) to Portland (PWM) cost?

According to Trip.com's data, the lowest price is around £265.
How long is the flight from Chicago (CHI) to Portland (PWM)?

It takes about 2 hours 24 minutes to fly from Chicago (CHI) to Portland (PWM).
What are the most popular airlines that fly from Chicago (CHI) to Portland (PWM)?

Airlines with flights from Chicago (CHI) to Portland (PWM): United Airlines and Air New Zealand.
What's the most popular airline for direct flights from Chicago (CHI) to Portland (PWM)?

United Airlines operates 5 direct flights from Chicago (CHI) to Portland (PWM).
How many airports in Portland (PWM)?

There are 1 airport(s) in Portland (PWM): Portland International Jetport.

How to find a cheap flight from Chicago to Portland

Wait until the last minute and flight costs are often sky-high. Plan ahead, book the right way, and your savings can soar. We have loads of saving tips to help you find a cheap flight from Chicago to Portland. Book your flights at the right time and save more.

Be flexible with your travel dates to get the cheapest flight from Chicago to Portland.

Simply tap "Date" on the flight search bar to browse through the calendar and check out airfare from Chicago to Portland over the next 6 months in 2025. If you're planning to fly within the next three months, it looks like the most affordable option is on Thu, Apr 10, with one-way flights priced at just £101.

Compare cheap flight deals from Chicago to Portland across hundreds of airlines.

With our extensive search, you can compare prices from over 500 airlines to find the cheapest flight tickets from Chicago to Portland. The cheapest airline for this route is United Airlines.

Set up a Price Alert

By setting up a Price Alert for your journey from Chicago to Portland, you can easily keep an eye on ticket prices without having to check every day.

Don't miss out on cheap flight deals and promo codes from Chicago to Portland.

You can always find the latest offers through Trip.com Deals and Promo Codes for cheap flights. By signing up for a free membership, you'll get access to even more deals for your flights.

Book early or wait until the last minute.

It's usually best to book early. Flight tickets are often cheapest when they're first released, typically about a year before the departure date. So, have a look online as soon as the flights you're interested in become available. If you miss the cheapest time, you might still find some good deals as the departure date gets closer.

Search for flights on the go.

For the best travel flight booking experience, download the Trip.com app. You can search for cheap flights from Chicago to Portland and snag some exclusive deals just for you.

Flight Information from Chicago to Portland

Cheapest one-way flight price	£56
Cheapest return ticket price	£170
Off-season travel month	February
Peak season for travel	December
Flight distance	1,425.81km
Average flight time	2 hours 24 minutes
Popular airline	United Airlines