ORD - PWM

$105 Find Cheap Flights from Chicago O'Hare Airport to Portland

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from O'Hare Intl to Portland departing on 1/20. 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

KAYAK searches hundreds of travel sites at once for deals on flights to Portland

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Portland, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Portland, as well as popular online travel agencies
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Everything you should know

Cheapest round-trip
$209
Overall average: $383
United Airlines
Wed 1/28Wed 2/4
ORD - PWM • Non-stop
Cheapest one-way
$105
Typical prices: $214-$359
United Airlines
Tue 1/20
ORD - PWM • Non-stop
Our travelers' advice
AI-powered summary based on content written by travel experts. AI can make mistakes.
American's Basic Economy has low fares but no free bags.
United's Economy Plus offers extra legroom in front rows.
Expert advice
Expert advice
Expert advice
Expert advice
Top airlines
United Airlines
Cheapest • from $209 (round-trip)
Delta
Best reviews • 7.9 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
When to book
4 weeks
in advance
Our data shows that travelers who book at least 4 weeks in advance save around 17% compared to booking last minute.
Insights
Insights
Insights
Insights
When to travel
September
Cheapest • 14% price drop
August
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!
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Flight Deals

Cheap Flights from O'Hare Intl to Portland (ORD-PWM)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from O'Hare Intl 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 O'Hare Intl to Portland

Wed, Jan 28 - Wed, Feb 4
United Airlines Logo
11:00 am - 2:39 pm
ORD
-
PWM
2h 39mnonstop
United Airlines Logo
4:10 pm - 6:18 pm
PWM
-
ORD
3h 08mnonstop
$209United Airlines
Fri, Mar 20 - Tue, Mar 24
American Airlines Logo
8:02 pm - 11:34 pm
ORD
-
PWM
2h 32mnonstop
American Airlines Logo
6:17 am - 8:34 am
PWM
-
ORD
3h 17mnonstop
$210American Airlines
Sat, Feb 14 - Fri, Feb 20
United Airlines Logo
11:48 am - 3:14 pm
ORD
-
PWM
2h 26mnonstop
United Airlines Logo
3:10 pm - 7:53 pm
PWM
-
ORD
5h 43m1 stop
$219United Airlines
Tue, Jan 20 - Wed, Jan 21
United Airlines Logo
11:00 am - 2:39 pm
ORD
-
PWM
2h 39mnonstop
United Airlines Logo
4:10 pm - 6:18 pm
PWM
-
ORD
3h 08mnonstop
$220United Airlines
Sat, Mar 21 - Tue, Mar 24
Delta Logo
7:10 am - 12:09 pm
ORD
-
PWM
3h 59m1 stop
Delta Logo
6:25 am - 12:57 pm
PWM
-
ORD
7h 32m1 stop
$229Delta
Tue, Jan 20 - Wed, Jan 21
United Airlines Logo
8:52 am - 2:31 pm
ORD
-
PWM
4h 39m1 stop
United Airlines Logo
4:10 pm - 6:18 pm
PWM
-
ORD
3h 08mnonstop
$230United Airlines
Sat, Feb 14 - Tue, Feb 17
Delta Logo
7:00 am - 1:43 pm
ORD
-
PWM
5h 43m1 stop
Delta Logo
2:35 pm - 11:56 pm
PWM
-
ORD
10h 21m2 stops
$234Delta
Fri, Feb 27 - Mon, Mar 2
American Airlines Logo
4:04 pm - 11:50 pm
ORD
-
PWM
6h 46m1 stop
American Airlines Logo
5:40 pm - 7:50 pm
PWM
-
ORD
3h 10mnonstop
$239American Airlines
Sat, Feb 14 - Fri, Feb 20
Delta Logo
3:21 pm - 12:18 am
ORD
-
PWM
7h 57m2 stops
Delta Logo
2:35 pm - 9:01 pm
PWM
-
ORD
7h 26m2 stops
$240Delta
Fri, Jan 16 - Tue, Jan 20
Delta Logo
5:40 pm - 11:22 pm
ORD
-
PWM
4h 42m1 stop
Delta Logo
5:57 pm - 10:34 pm
PWM
-
ORD
5h 37m1 stop
$249Delta
Booking Insights

KAYAK's insights & trends for O'Hare Intl to Portland flights

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

What’s the cheapest day of the week to fly from Chicago O'Hare Airport to Portland?

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

Your flight ticket price will generally be cheaper if you fly to Portland on a Tuesday and more expensive on a Thursday. On your return trip to Chicago O'Hare Airport, you should consider flying back on a Thursday, and avoid Sundays for better deals.

What is the cheapest month to fly from Chicago O'Hare Intl Airport to Portland?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Chicago O'Hare Intl Airport 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 O'Hare Intl Airport to Portland is September, where tickets cost $329 (return) on average. On the other hand, the most expensive months are December and February, where the average cost of round-trip tickets is $441 and $437 respectively.

Can I save money by flying with a layover from Chicago O'Hare Intl Airport 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.

No, with an average price for the route of $349, prices are generally cheapest when you fly direct.

How far in advance should I book a flight from Chicago O'Hare Intl Airport 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 O'Hare Intl Airport 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 O'Hare Intl Airport to Portland, you should book around 4 weeks before departure, which saves you about 17% 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 O'Hare Intl 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.
Airlines
Frontier

Economy Bundle includes a carry-on bag and seat choice, ideal for budget travelers.


Premium Bundle offers priority boarding and extra legroom for a small additional cost.

United Airlines

Economy Plus provides extra legroom and is located in the front rows of the economy cabin.


United offers free messaging on most flights, though streaming may incur a fee.

American Airlines

Basic Economy offers low fares but includes late boarding and no free checked bags.


Main Cabin Extra provides early boarding and complimentary drinks for a small upgrade fee.

Our travel experts
Stefanie Waldek

Stefanie Waldek

Expert on Frontier and United Airlines

Stefanie Waldek

Stefanie Waldek

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.

Read more
Harriet Baskas

Harriet Baskas

Expert on American Airlines

Harriet Baskas

Harriet Baskas

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.

Read more

Good to know

Low seasonFebruary
Cheapest flight$105
Best time to beat the crowds but there is an average 14% increase in price.
Most popular time to fly and prices are also 10% lower on average.
Flight from Chicago O'Hare Airport to Portland

When to book flights from O'Hare Intl to Portland

Are your dates flexible? Find out the best times to travel from O'Hare Intl 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 Chicago O'Hare Airport to Portland flights

  • What is the cheapest flight from Chicago O'Hare Intl Airport to Portland?

    In the last 3 days, the lowest price for a flight from Chicago O'Hare Intl Airport to Portland was $105 for a one-way ticket and $209 for a round-trip.

  • Do I need a passport to fly between Chicago O'Hare Airport and Portland?

    A passport is not required to fly from Chicago O'Hare Airport to Portland.

  • Which airports will I be using when flying from Chicago O'Hare Airport to Portland?

    When flying out of Chicago O'Hare Airport you will be using Chicago O'Hare Intl. You will be landing at Portland, also known as Portland.

  • Which airlines offer Wi-Fi service onboard planes from Chicago O'Hare Airport to Portland?

    American Airlines, and JetBlue offer inflight Wi-Fi service on the Chicago O'Hare Airport to Portland flight route.

  • Which aircraft models fly most regularly from Chicago O'Hare Airport to Portland?

    The Embraer 175 (Enhanced Winglets) is the aircraft model that flies most regularly on the Chicago O'Hare Airport to Portland flight route.

  • Which airline alliances offer flights from Chicago O'Hare Airport to Portland?

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

  • On which days can I fly direct from Chicago O'Hare Airport to Portland?

    There are nonstop flights from Chicago O'Hare Airport to Portland on a daily basis.

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

    The two airlines most popular with KAYAK users for flights from Chicago to Portland are Delta and United Airlines. With an average price for the route of $479 and an overall rating of 7.9, Delta is the most popular choice. United Airlines is also a great choice for the route, with an average price of $378 and an overall rating of 7.4.

  • How does KAYAK find such low prices on flights from Chicago O'Hare Airport 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 O'Hare Airport to Portland.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Portland from Chicago O'Hare Airport 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 O'Hare Airport 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 O'Hare Airport with another airline. Booking your flights between Chicago O'Hare Airport and PWM can sometimes prove cheaper using this method.

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

  • Looking for a cheap flight? 25% of our users found flights on this route for $330 or less one-way and $279 or less round-trip.

Prefer to fly direct from Chicago O'Hare Airport to Portland?

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

Direct departures

Chicago O'Hare Intl to Portland

Monday

American Airlines, United Airlines

American Airlines, United Airlines

Tuesday

American Airlines, United Airlines

American Airlines, United Airlines

Wednesday

American Airlines, United Airlines

American Airlines, United Airlines

Thursday

American Airlines, United Airlines

American Airlines, United Airlines

Friday

American Airlines, United Airlines

American Airlines, United Airlines

Saturday

American Airlines, United Airlines

American Airlines, United Airlines

Sunday

American Airlines, United Airlines

American Airlines, United Airlines

See more direct flights

Direct returns

Portland to Chicago O'Hare Intl

Monday

American Airlines, United Airlines

American Airlines, United Airlines

Tuesday

American Airlines, United Airlines

American Airlines, United Airlines

Wednesday

American Airlines, United Airlines

American Airlines, United Airlines

Thursday

American Airlines, United Airlines

American Airlines, United Airlines

Friday

American Airlines, United Airlines

American Airlines, United Airlines

Saturday

American Airlines, United Airlines

American Airlines, United Airlines

Sunday

American Airlines, United Airlines

American Airlines, United Airlines

See more direct flights

Reviews of the top 3 airlines serving from O'Hare Intl to Portland

 
See real verified KAYAK customer reviews for airlines flying from Chicago to Portland. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from O'Hare Intl to Portland? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
7.9
DeltaOverall score based on 8021 reviews
7.8Entertainment
8.5Crew
7.2Food
8.1Boarding
7.9Comfort
Airline reviews

This flight was no comparison to our prior flight. I'm thinking it all has to do with the age of the aircraft.

10.0 ExcellentAnonymous, Dec 2025
DCA - SEA
Read more Delta reviews

This flight was no comparison to our prior flight. I'm thinking it all has to do with the age of the aircraft.

This flight was a first class choice and left much to be desired. Seat backs on seats were falling apart and torn. Seats actually didn't come to a "full & upright position". Pull out table was sprung. Not any significant leg room. All in all we were on an obviously older plane and felt overcharged for what we received as first class.

Flight was delayed several times. At one point, they "pulled back" 15 minutes from the delayed boarding and sent a text saying we would board sooner than previously advised. The flight then was delayed again. And when we boarded, there was an unspecified technical issue which had us waiting in the plane for about an hour.

Delta is a good airline. I've never had an issue with Delta. I'll continue to fly with them until they show me that I shouldn't.

The only thing nice I can say is the flight crew was really nice and apologetic about the situation. They shared as much information as they had and advised us on what we could do about missing connecting flights. The boarding process was so slow. The gate agent was working by herself and should have had someone working with her. It took almost an hour to board because she was trying to board a full flight of people and provide customer service to everyone who was flying standby and/or had questions. It was really chaotic. This didn't help the fact that we were delayed and folks were missing connections the longer it took.

The gate attendants and the crew were terrible. Because of high winds, they needed to carry more fuel, so they had to get volunteers to take the next flight at 6 am the next day. They did a terrible job of it - our flight ended up taking off just under 3 hours of the scheduled time. I hope to never fly Delta again.

Did not realize internet screen was hidden between seats and no info printed!!!!

2 of the seats in row 31 the entertainment system was not working, and one seat the tray table did not go all the way down. Flight arrived early and departed on time which was great.

Very good flight crew and very nice people staff were incredible especially the gate agent

Waited at the usual crowded gate at DCA where one ends up standing up because there aren't enough seats.

I understand weather is an issue, but making us chase our plane down at five scheduled gates across three terminals in an airport the size of O'Hare was unfair. They'd have probably been better off to leave gates as TBD until the inbound plane is in final approach instead of running us all over the place. Also, props to the consistently-unprepared ground crew in Richmond for once again leaving my lane parked short of the gate because they couldn't have a crew in place on time with 2 hours notice...

cabin crew was OK, food was OK, the trip from the US to Munich was actually pretty bad comfort wise. Noisy aircraft, lights never dimmed even in Business class (night flight) barely sufficient amenities for the price. I have millions of miles with United but TBH American is gaining ground and Delta has always been marginally better then United although on paper United has more longes and cheaper upgrades.

Essy to get on. The hostess gave very little pop, the plane was late getting in, and we are still waiting for our bags. This sucks. :/

Great flight. On time boarding. Smooth flight and on time arrival at EWR. The flight crew was marvelous and there was a great selection of movies on the entertainment system. Our bags were at the carousel before we got there. Another excellent flight from United.

I liked the snacks and the flight attendants were friendly.

After a delay at the gate, C3, at Ohare on Sunday, I left my Blk ski coat on the bench at the gate, lost! Please review my lob claim, thx.

Very thoughtful flight attendant offered me water immediately since I had run to make my connection.

Always wish for more healthy, gluten free options. We have to bring our own.

Having a long layover, I was very appreciative of the ability to stand by for an earlier flight. Other airlines like Delta have refused this to me in the past, just to be mean (because my ticket class wasn't high enough). United went out of their way to help me get to my destination early, which I really appreciated given that it was the third leg of a 24+ hour journey for me.

Other than a way way too cold cabinets for the entire flight, all was great

Crew were all friendly and helpful. It was a short flight so just a beverage service with a cookie. After we were boarded the plane took about 45 minutes to leave the gate but it was New Year’s Eve so not shocking there was some delay. Overall good experience and very grateful.

The boarding process needs to be fixed. The zone don't work, especially when there is hardly anyone in zones 3, 4,and 5, leaving the majority of the passengers backed up in the aisle, especially because passengers seated near the front are blocking passengers who are seated in the rear of the plane. It would also help if the size of carry on bags was more strictly enforced.

The boarding by groups is pointless. The first two groups worked fine, but almost Noone boarded in goups three thru five leaving the vast majority boarding when group six was called. It defeated the purpose of spreading out the crowd.

We loved the steward on the plane. He made the night enjoyable

The plane was late, when we did board the plane was as cold as a freezer. I was freezing the entire flight, no blankets. Lost miserable flight I’ve ever had.

3 hour weather delay followed by 1 hour (and counting) maintenance delay. UGH!

After we'd boarded , they canceled the flight. The crew didn't even know , we just all received text messages. Then after they deplaned us , AA was just like "too bad, go F your self, we sure ain't gonna help you"

After a two hour delay, my flight was CANCELLED! No pilot available. Such BS.

Amazing food, great staff, with one noticable detail missing ...but no seat entertainment in any of aircraft ...I am not a fan

I wish American Airlines would change the airline industry by loading the plane back to front instead of front to back. Planes would board so much more smoothly and quickly.

Everything you need to know for your flight from O'Hare Intl to Portland

Information on your arrival and departure airports