Trip.com
>
Flights
>
Flights to United States
>
Flights to Oregon
>
Flights to Portland
Hotels in Portland
>
Flights from Chicago to Portland

Find cheap airlines flights from Chicago to Portland

Choose from 6 carriers that fly from Chicago to Portland, including Alaska Airlines, Spirit Airlines, and Hawaiian Airlines. Enjoy the cheapest tickets on this route with Hawaiian Airlines.
Alaska Airlines logo Alaska Airlines Spirit Airlines logo Spirit Airlines Hawaiian Airlines logo Hawaiian Airlines Frontier Airlines logo Frontier Airlines American Airlines logo American Airlines United Airlines logo United Airlines

Cheap flight deals from Chicago to Portland

Non stop flight deals! Book direct flights from Chicago to Portland: One way flights from $48, round trip flights from $87. 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 2,816.22 km. It takes around 4 hours 30 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 $48
Cheapest round-trip ticket price $87
Off-season for travel April
Peak season for travel March
Flight distance 2,816.22 km
Average flight time 4 hours 30 minutes
Popular airline Alaska Airlines

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

The cheapest time for Chicago to Portland flights: Aug 10 to Aug 17 — one way flight prices from $46.

Cheapest flights
From price
Search
  • 6 13
  • 13 20
  • 20 27

  • Aug

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

  • Sep

    31 7
  • 7 14
  • 14 21
  • 21 28
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 (PDX) the cheapest?

    Airlines adjust prices for flights from Chicago to Portland 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 Chicago (CHI) to Portland (PDX) cost?

    According to Trip.com's data, the lowest price is around $346.

  • How long does it take to fly from Chicago (CHI) to Portland (PDX) and what is the distance?

    It takes around 4 hours 30 minutes to fly from Chicago (CHI) to Portland (PDX).

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

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
Be flexible with your travel dates to get the cheapest Chicago to Portland ticket.
Tap "Date" in the flight search bar to browse the calendar and find airfare from Chicago to Portland for the next six months in 2025. If you're looking to fly within the next three months, the lowest fare is $48 for a one-way ticket on Thu, Aug 7.
2
Compare cheap Chicago to Portland flight deals from hundreds of airlines.
Our powerful search system compares prices from over 500 airlines. So you can find the cheapest flights from Chicago to Portland. The most affordable airline currently operating on this route is Hawaiian Airlines.
3
Set up a Price Alert to track fare drops.
Set up a Price Alert for your Chicago to Portland route to track ticket prices effortlessly—no need to check manually every day.
4
Don't miss out on cheap Chicago to Portland 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.
5
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.
6
Search for flights on the go.
For the best booking experience on the go, download Trip.com and search for cheap flights from Chicago to Portland to access exclusive deals just for you.

More Travel Options