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

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
6 13

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 departure date and time of your selection. By analyzing data from all airlines, we've discovered that 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 Rp 6,277,278.
How long does it take to fly from Portland (PWM) to Chicago (CHI) and what is the distance?

It takes around 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 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.

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

Tap "Date" in the flight search bar to browse the calendar and find airfare from Portland to Chicago for the next six months in 2025. If you're looking to fly within the next three months, the lowest fare is Rp 2009932 for a one-way ticket on Sat, May 24.

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

Our powerful search system compares prices from over 500 airlines. So you can find the cheapest flights from Portland to Chicago. The most affordable airline currently operating on this route is United Airlines.

Set up a Price Alert to track fare drops.

Set up a Price Alert for your Portland to Chicago route to track ticket prices effortlessly—no need to check manually every day.

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

Stay updated on the latest deals with Trip.com Deals and Promo Codes for cheap flights. Sign up for a free membership to unlock even more exclusive flight discounts.

Book early or wait unitl the last minute to fine the best fares.

It's always better to book early! Airlines typically release their lowest fares about a year before departure, so check as soon as flights become available. If you miss that window, you may still find great deals closer to your travel date.

Search for flights on the go.

For the best booking experience on the go, download Trip.com and search for cheap flights from Portland to Chicago to access exclusive deals just for you.

Flight Info | Portland to Chicago

Cheapest one-way flight price	Rp 1,628,299
Cheapest round-trip ticket price	Rp 3,992,108
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