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Flights from Chicago to Portland

Cheap flight deals from Chicago to Portland

Non stop flight deals! Book direct flights from Chicago to Portland: One way flights from KWD 22, round trip flights from KWD 48. Cheapest next 3 months.

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

Flight Info | Chicago to Portland

The distance between Chicago and Portland is about 1,425.81 km. It takes around 2 hours 29 minutes on average to fly from Chicago to Portland. The most popular month to Portland is March. The off-season for travel is April.

Cheapest one-way flight price KWD 22
Cheapest return ticket price KWD 48
Off-season for travel April
Peak season for travel March
Flight distance 1,425.81 km
Average flight time 2 hours 29 minutes

When is the cheapest time to fly from Chicago to Portland?

The cheapest time for Chicago to Portland flights: Aug 17 to Aug 24 — one way flight prices from KWD 21.

Cheapest flights
From price
Search
  • 20 27

  • Aug

    27 3
  • 3 10
  • 10 17
  • 17 24
  • 24 31

  • Sep

    31 7
  • 7 14
  • 14 21
  • 21 28

  • Oct

    28 5
  • 5 12
Displayed prices are calculated based on the cheapest average weekly prices of the corresponding route on Trip.com.

Frequently Asked Questions

  • 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 lowest flight prices on Tuesdays, Wednesdays, and Saturdays.
  • According to Trip.com's data, the lowest price is around KWD 106.
  • It takes about 2 hours 29 minutes to fly from Chicago (CHI) to Portland (PWM).
  • Airlines with flights from Chicago (CHI) to Portland (PWM): Emirates, United Airlines, Air New Zealand, Qatar Airways, Southwest Airlines and American Airlines.
  • There are 1 airport(s) near 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.
1
Being flexible with your dates to get the cheapest Chicago to Portland ticket.
Tap "Date" on flight search bar to scan through the calender for Chicago to Portland airfare over next 6 months in 2025. If you would like to fly in next 3 months, it seems the cheapest date is on Sat, Aug 23 at KWD 22 for one-way flights.
2
Compare cheap Chicago to Portland flight deals from over hundreds of airlines.
Our extensive search allows you to compare prices from over 500 airlines to choose the cheapest flight tickets from Chicago to Portland. The cheapest airline operating is American Airlines.
3
Set up a Price Alert
By setting up a Price Alert for your Chicago to Portland route, you can easily track the price of your airline tickets from without manually checking every day.
4
Don't miss cheap Chicago to Portland flight deals and promo codes.
You can always get the latest deals through Trip.com Deals and Promo Codes for cheap flights. If registering a free membership, you can receive more deals for your flights.
5
Book early or wait unitl the last minute.
It's always better to book early. Flight tickets tend to be the cheapest when they are first released, normally about a year before the departure date. So, check online as soon as the flights you want become available. If you miss the cheapest time, you can still find lower-priced tickets as the flight date approaches.
6
Search for flights on the go.
To get the best flight booking experience on the go, download Trip.com and search for cheap flight tickets from Chicago to Portland to get exclusive deals for you.

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