CHI - PDX

$160 Find Cheap Flights from Chicago to Portland - Compare and Save

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Chicago to Portland departing on 8/12. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy, 0 bags

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Everything you should know

Cheapest round-trip
$300
Typical prices: $255-$442
Frontier
Tue 9/1Tue 9/8
ORD - PDX • 1 stop
Cheapest non-stop
$350
Typical prices: $256-$439
Alaska Airlines
Sat 10/31Wed 11/18
ORD - PDX • Non-stop
Advice from real travelers
AI-powered summary based on content written by travel experts. AI can make mistakes.
United Economy Plus adds up to six inches more legroom on this medium-haul route.
Alaska Premium Class adds priority boarding and legroom; Southwest offers free snacks.
Expert advice
Expert advice
Expert advice
Expert advice
Nonstop flights
You can fly direct with Alaska Airlines, American Airlines and others. Average duration is 4h 28m
Direct flights
Direct flights
+1
+1
Direct flights
Direct flights
+1
Top routes
Cheapest • 12% average savings
Most popular
Insights
Insights
Insights
Insights
Top layover airports
Cheapest • Avg $224 (round-trip)
Shortest trip • 6h 04m (one-way)
Insights
Insights
Insights
Insights
When to book
in advance
Our data shows that travelers who book at least 4 weeks in advance save around 54% compared to booking last minute.
Insights
Insights
Insights
Insights
When to travel
Cheapest • 16% price drop
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
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We hope you love your trip to Portland!
Flight Deals
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Flight Deals

Cheap Flights from Chicago to Portland (CHI-PDX)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Chicago to Portland that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Chicago to Portland

Tue, Sep 1 - Tue, Sep 8
Frontier Logo
2:41 pm - 5:11 pm
ORD
-
PDX
28h 30m
1 stop
Frontier Logo
5:56 pm - 2:17 pm
PDX
-
ORD
18h 21m
2 stops
$300Frontier
Fri, Oct 2 - Thu, Oct 8
Frontier Logo
6:30 am - 11:43 am
ORD
-
PDX
7h 13m
1 stop
Frontier Logo
9:34 pm - 11:57 am
PDX
-
ORD
12h 23m
1 stop
$300Frontier
Sat, Aug 15 - Sat, Aug 29
Multiple Airlines Logo
7:20 am - 9:45 am
ORD
-
PDX
4h 25mnonstop
Multiple Airlines Logo
5:56 pm - 5:59 am
PDX
-
ORD
10h 03m
1 stop
$303Multiple Airlines
Wed, Aug 26 - Thu, Aug 27
Multiple Airlines Logo
2:22 pm - 4:50 pm
ORD
-
PDX
4h 28mnonstop
Multiple Airlines Logo
5:56 pm - 5:59 am
PDX
-
ORD
10h 03m
1 stop
$303Multiple Airlines
Wed, Sep 9 - Wed, Sep 16
Alaska Airlines Logo
2:22 pm - 4:50 pm
ORD
-
PDX
4h 28mnonstop
Alaska Airlines Logo
3:00 pm - 11:59 pm
PDX
-
ORD
6h 59m
1 stop
$341Alaska Airlines
Tue, Sep 8 - Tue, Sep 15
Alaska Airlines Logo
6:00 am - 1:37 pm
ORD
-
PDX
9h 37m
1 stop
Alaska Airlines Logo
3:00 pm - 11:59 pm
PDX
-
ORD
6h 59m
1 stop
$345Alaska Airlines
Wed, Sep 9 - Wed, Sep 16
American Airlines Logo
8:15 am - 10:55 am
ORD
-
PDX
4h 40mnonstop
American Airlines Logo
6:01 am - 12:15 pm
PDX
-
ORD
4h 14mnonstop
$355American Airlines
Mon, Aug 17 - Mon, Aug 24
American Airlines Logo
9:00 am - 11:34 am
ORD
-
PDX
4h 34mnonstop
American Airlines Logo
5:59 am - 12:12 pm
PDX
-
ORD
4h 13mnonstop
$356American Airlines
Thu, Aug 13 - Wed, Aug 19
Southwest Logo
8:50 pm - 11:05 pm
MDW
-
PDX
4h 15mnonstop
Southwest Logo
11:30 pm - 5:25 am
PDX
-
MDW
3h 55mnonstop
$357Southwest
Wed, Oct 7 - Tue, Oct 13
Southwest Logo
10:05 am - 12:30 pm
MDW
-
PDX
4h 25mnonstop
Southwest Logo
11:35 pm - 5:25 am
PDX
-
MDW
3h 50mnonstop
$357Southwest
Booking Insights

KAYAK's insights & trends for Chicago to Portland flights

Get data-powered insights and trends into flights from Chicago to Portland to help you find the cheapest flights, the best time to fly and much more.

How much is a round-trip flight from Chicago to Portland?

This analysis is based on the cheapest round-trip price found on KAYAK in the last 12 months by searching for a flight from Chicago to Portland departing in October.

Flight prices are below average for this route right now.

Flights to Portland from Chicago usually cost between $322 and $497 in October.
The lowest price found in the past 5 days was $300 on Frontier (Oct 2-Oct 8).

What is the cheapest Chicago to Portland flight route?

Data is based on round-trip flight searches on KAYAK over the past month.

The cheapest return flight from Chicago to Portland costs $241 on the route between Chicago O'Hare Intl Airport (ORD) and Portland (PDX). Over the past month, this route was, on average, 12% cheaper than other Chicago-Portland routes. It is also the most popular route.

What’s the cheapest day of the week to fly from Chicago to Portland?

The average price of all round-trip flights from Chicago to Portland clicked on KAYAK for each day over the last 12 months.

If you are looking for a flight deal from Chicago to Portland, look for departures on Tuesdays and avoid leaving on a Sunday, as it's usually the priciest day. When flying back from Portland, Wednesday is the cheapest day to fly and Sunday is the most expensive.

What is the cheapest month to fly from Chicago to Portland?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Chicago to Portland, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Chicago to Portland is February, where tickets cost $289 (return) on average. On the other hand, the most expensive months are March and July, where the average cost of round-trip tickets is $390 and $381 respectively.

Can I save money by flying with a layover from Chicago to Portland?

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

Yes, flying with a layover may cost you more time, but you can also save money on the route, with a 1 stop layover the cheapest option at $386 on average.

How far in advance should I book a flight from Chicago to Portland?

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from Chicago to Portland, removes the top 0.1% to account for outliers, and then takes the average of all the values for each week.

To get a below average price on the flight from Chicago to Portland, you should book around 4 weeks before departure, which saves you about 54% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 18 weeks before departure.

Expert advice

Expert advice for your flight from Chicago to Portland

 
AI-powered summary based on content written by travel experts. AI can make mistakes.
KAYAK teamed up with top travel experts to share the best tips for your journey.
Our travel experts
Stefanie Waldek

Stefanie Waldek

Expert on United Airlines, ORD and MDW

Stefanie Waldek is a freelance space, travel, and design writer based in Saratoga Springs, NY. Her words have appeared in Space.com, Travel + Leisure, Condé Nast Traveler, Architectural Digest, and House Beautiful, among other publications. An expert in aviation and expedition cruising, Stefanie is frequently up in the air or on the sea, likely en route to Antarctica or the Arctic.

Harriet Baskas

Harriet Baskas

Expert on Alaska Airlines

Harriet is an award-winning journalist who is happiest in an airport or an unusual museum. Her stories about airports, air travel, and the business of travel have appeared on NBC News, CNBC, USA TODAY, The Points Guy and other outlets. She is the creator of the StuckatTheAirport.com blog and the author of nine books. When not out on the road or exploring the latest airport amenities, she’s home in Seattle getting ready for the next adventure.

Blane Bachelor

Blane Bachelor

Expert on Southwest

Blane Bachelor is a journalist and editor specializing in travel and aviation who writes regularly for top global outlets. Born and raised in Florida, Blane has worked and lived in four countries, including the Netherlands, where she’s currently based with her family. Her favorite way to get to know a new destination is by running or riding a bike around town – or hearing a spooky ghost story about local history. She will always choose the window seat.

Gabriel Leigh

Gabriel Leigh

Expert on PDX

Gabriel is a writer and video creator. As senior content producer for Flightradar24 and Monocle’s transport correspondent, he keeps a close eye on aviation in particular. He has also written travel articles for the likes of The New York Times. Born in New York but raised around the world, he now lives in Sweden. He’s been to 75 countries, flying 2.3 million miles on 113 airlines and through 234 airports in the process.

Good to know

Low season

February

Cheapest flight

$160
Best time to beat the crowds with an average 21% drop in price.
Most popular time to fly with an average 11% increase in price.
Flight from Chicago O'Hare Airport to Portland

When to book flights from Chicago to Portland

Are your dates flexible? Find out the best times to travel from Chicago to Portland based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs for booking flights from Chicago to Portland

  • Can I fly out of Chicago with pets?

    Traveling with your pet out of Chicago is a breeze as both O’Hare International Airport and Midway International Airport are pet friendly. The pet relief stations in O’Hare International Airport are located at Terminals 1, 2, 3, 5, and the Multi-Modal Facility. Midway International Airport also has pet relief stations located both outside and inside the terminal. The pet relief station located inside the terminal is just past the Concourse A security checkpoint and features artificial turf and an automatic flushing system for easy cleanup.

  • Which airport is best for people with disability needs?

    If you may require accessibility services, you should consider flying out of Midway International Airport. The airport is less crowded than O’Hare International Airport, meaning that most areas and facilities will be available for use. The airport also provides a multitude of accessibility features, such as wheelchair-accessible restrooms and elevators with raised numerals and Braille. The airport also provides parking spots for people with disabilities, which are wide enough for ramp and lift access.

  • How do I get from Portland International Airport to downtown Portland?

    The easiest and most convenient way to get from Portland International Airport to downtown Portland is by using the Max Light rail Red Line, which will take you less than 40min. The last train leaves the airport at 11:50 pm. You can also decide to use private means, such as taxicabs, ridesharing services, or car rental from any of the several car rental companies that operate from within the airport.

  • How do I get from downtown Chicago to O’Hare International Airport?

    Getting to O’Hare International Airport from downtown Chicago is made easy by the city’s intricate public transportation system. You can conveniently use the CTA L Trains to get from the city to the airport, as well as the airport shuttle services that transport passengers to the airport. Additionally, the airport has multiple parking options that allow you to drive to the airport and leave your vehicle for either a short or a long time.

  • What is the cheapest flight from Chicago to Portland?

    In the last 5 days, the lowest price for a flight from Chicago to Portland was $160 for a one-way ticket and $300 for a round-trip.

  • Do I need a passport to fly between Chicago and Portland?

    No, a passport isn't needed to fly from Chicago to Portland. However, local authorities might ask for an official ID.

  • Which airports will I be using when flying from Chicago to Portland?

    There are 2 airports in Chicago (Chicago Midway and Chicago O'Hare Intl.) and only 1 airport in Portland (Portland). The cheapest flights are generally found on the Chicago O'Hare Airport to Portland flight route.

  • Which airlines offer Wi-Fi service onboard planes from Chicago to Portland?

    American Airlines, Alaska Airlines, JetBlue, Hawaiian Airlines, and Delta offer inflight Wi-Fi service on the Chicago to Portland flight route.

  • Which aircraft models fly most regularly from Chicago to Portland?

    The Boeing 737-800 is the aircraft model that flies most regularly on the Chicago to Portland flight route.

  • Which airline alliances offer flights from Chicago to Portland?

    Star Alliance, and oneworld are the airline alliances operating flights between Chicago and Portland, with Star Alliance being the most commonly used for this route.

  • On which days can I fly direct from Chicago to Portland?

    There are nonstop flights from Chicago to Portland on a daily basis.

  • Which is the best airline for flights from Chicago to Portland, Southwest or Alaska Airlines?

    The two airlines most popular with KAYAK users for flights from Chicago to Portland are Southwest and Alaska Airlines. With an average price for the route of $325 and an overall rating of 8.0, Southwest is the most popular choice. Alaska Airlines is also a great choice for the route, with an average price of $332 and an overall rating of 7.9.

  • How does KAYAK find such low prices on flights from Chicago to Portland?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Chicago to Portland.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Chicago to Portland?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Portland from Chicago is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Chicago to Portland?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Portland with an airline and back to Chicago with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Chicago to Portland?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Portland from Chicago up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

KAYAK’s top tips for finding a cheap flight from Chicago to Portland

  • Looking for a cheap flight? 25% of our users found flights on this route for $209 or less one-way and $341 or less round-trip.
  • When traveling out of Chicago, you have the option of departing from any of the two major international airports serving the city: O’Hare International Airport (ORD) or Midway International Airport (MDW).
  • If you have an early flight from Chicago to Portland, consider departing from O’Hare International Airport as the airport has a hotel on its premises where you can book a stay for the night to allow you to be on time for your early morning flight.
  • If you need to get some work done or relax after your flight into Portland International Airport (PDX), make use of the several lounges available at the airport. These lounges are located inside security at Concourse C, D, and E, while there is one lounge located outside security at the Main Terminal.
  • Midway International Airport as the airport provides lactation pods where mothers can breastfeed or pump in a private and safe space. You can find the lactation pod at Concourse A, next to Gate A5.
  • If you misplace any of your items when traveling out of O’Hare International Airport, make sure to contact the organization closest to where you last saw the items. You can contact any of the following agencies: Parking Facilities, food service, TSA Checkpoints, On the Airport Transit Systems, or the Customs Area.

Prefer to fly direct from Chicago to Portland?

 
Direct data is based off flight results for the next 60 days. Find direct flights from all airlines flying direct from Chicago to Portland.
Find which airlines fly direct from Chicago to Portland Airport, which days they fly and book direct flights.

Direct departures

Chicago to Portland

Monday

Alaska Airlines,American Airlines,Southwest, +1 more

Alaska Airlines,American Airlines, +2 more

Tuesday

Alaska Airlines,American Airlines,Southwest, +1 more

Alaska Airlines,American Airlines, +2 more

Wednesday

Alaska Airlines,American Airlines,Southwest, +1 more

Alaska Airlines,American Airlines, +2 more

Thursday

Alaska Airlines,American Airlines,Southwest, +1 more

Alaska Airlines,American Airlines, +2 more

Friday

Alaska Airlines,American Airlines,Southwest, +1 more

Alaska Airlines,American Airlines, +2 more

Saturday

Alaska Airlines,American Airlines,Southwest, +1 more

Alaska Airlines,American Airlines, +2 more

Sunday

Alaska Airlines,American Airlines,Southwest, +1 more

Alaska Airlines,American Airlines, +2 more

See more direct flights

Direct returns

Portland to Chicago

Monday

Alaska Airlines,American Airlines,Southwest, +1 more

Alaska Airlines,American Airlines, +2 more

Tuesday

Alaska Airlines,American Airlines,Southwest, +1 more

Alaska Airlines,American Airlines, +2 more

Wednesday

Alaska Airlines,American Airlines,Southwest, +1 more

Alaska Airlines,American Airlines, +2 more

Thursday

Alaska Airlines,American Airlines,Southwest, +1 more

Alaska Airlines,American Airlines, +2 more

Friday

Alaska Airlines,American Airlines,Southwest, +1 more

Alaska Airlines,American Airlines, +2 more

Saturday

Alaska Airlines,American Airlines,Southwest, +1 more

Alaska Airlines,American Airlines, +2 more

Sunday

Alaska Airlines,American Airlines,Southwest, +1 more

Alaska Airlines,American Airlines, +2 more

See more direct flights

Everything you need to know for your flight from Chicago to Portland

Information on your arrival and departure airports