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Flights from Portland to Chicago

Find cheap airlines flights from Portland to Chicago

Choose from 1 carriers that fly from Portland to Chicago, including American Airlines, Enjoy the cheapest tickets on this route with Hawaiian Airlines.
American Airlines logo American Airlines

Cheap flight deals from Portland to Chicago

Non stop flight deals! Book direct flights from Portland to Chicago: One way flights from AED 179, round trip flights from AED 350. Cheapest next 3 months.

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

Flight Info | Portland to Chicago

The distance between Portland and Chicago is about 2,816.22 km. It takes around 4 hours on average to fly from Portland to Chicago. The most popular month to Chicago is March. The off-season for travel is May.

Cheapest one-way flight price AED 179
Cheapest return ticket price AED 350
Off-season for travel May
Peak season for travel March
Flight distance 2,816.22 km
Average flight time 4 hours
Popular airline American Airlines

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

The cheapest time for Portland to Chicago flights: Aug 24 to Aug 31 — one way flight prices from AED 178.

Cheapest flights
From price
Search
  • 13 20
  • 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
Displayed prices are calculated based on the cheapest average weekly prices of the corresponding route on Trip.com.

Frequently Asked Questions

How to find a cheap flight from Portland to Chicago

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 Portland to Chicago. Book your flights at the right time and save more.
1
Being flexible with your dates to get the cheapest Portland to Chicago ticket.
Tap "Date" on flight search bar to scan through the calender for Portland to Chicago airfare over next 6 months in 2025. If you would like to fly in next 3 months, it seems the cheapest date is on Thu, Aug 28 at AED 179 for one-way flights.
2
Compare cheap Portland to Chicago 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 Portland to Chicago. The cheapest airline operating is Hawaiian Airlines.
3
Set up a Price Alert
By setting up a Price Alert for your Portland to Chicago route, you can easily track the price of your airline tickets from without manually checking every day.
4
Don't miss cheap Portland to Chicago 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 Portland to Chicago to get exclusive deals for you.

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