Trip.com
>
Flights
>
Flights to United States
>
Flights to Illinois
>
Flights to Chicago
>
Flights from Portland to Chicago

Cheap flight deals from Portland to Chicago

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

  • Round-trip
  • One way

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

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

We monitor flight fares to help you find the best deals effortlessly

Cheapest flights
From price
Search
  • 13 20
  • 20 27

  • May

    27 4
  • 4 11
  • 11 18
  • 18 25

  • Jun

    25 1
  • 1 8
  • 8 15
  • 15 22
  • 22 29

  • Jul

    29 6
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 Portland (PWM) to Chicago (CHI) the cheapest?

    Airlines adjust prices for flights from Portland to Chicago 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.

  • How much do flights from Portland (PWM) to Chicago (CHI) cost?

    According to Trip.com's data, the lowest price is around AED 1,363.

  • How long does it take to fly from Portland (PWM) to Chicago (CHI)?

    It takes about 2 hours 58 minutes to fly from Portland (PWM) to Chicago (CHI).

  • What are the most popular airlines that fly from Portland (PWM) to Chicago (CHI)?

    Airlines with flights from Portland (PWM) to Chicago (CHI): United Airlines, Emirates and Air New Zealand.

  • How many airports are there in Chicago (CHI)?

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 Sat, May 24 at AED 436 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 United 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.

Flight Info | Portland to Chicago

Cheapest one-way flight price AED 353
Cheapest return ticket price AED 801
Off-season for travel March
Peak season for travel June
Flight distance 1,425.81 km
Average flight time 2 hours 58 minutes
Popular airline Jetblue Airways

More Travel Options

  • Top Routes from Portland
  • Top Routes to Chicago
  • Trending Airlines