ORD - PWM

$66 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 8/11. 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

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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Flights 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

Sat, Oct 25 - Thu, Oct 30
Southwest Logo
12:40 pm - 8:05 pmORD-PWM
6h 25m1 stop
Southwest Logo
9:15 am - 12:45 pmPWM-ORD
4h 30m1 stop
$130Southwest
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Sat, Aug 23 - Sat, Aug 30
American Airlines Logo
8:13 pm - 11:59 pmORD-PWM
2h 46mnonstop
American Airlines Logo
6:30 am - 8:32 amPWM-ORD
3h 02mnonstop
$131American Airlines
Find Deal
Sat, Oct 25 - Thu, Oct 30
Southwest Logo
12:40 pm - 10:25 pmORD-PWM
8h 45m2 stops
Southwest Logo
9:15 am - 12:45 pmPWM-ORD
4h 30m1 stop
$135Southwest
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Sat, Oct 25 - Thu, Oct 30
Southwest Logo
7:30 am - 8:05 pmORD-PWM
11h 35m2 stops
Southwest Logo
9:15 am - 12:45 pmPWM-ORD
4h 30m1 stop
$141Southwest
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Fri, Oct 31 - Mon, Nov 3
United Airlines Logo
6:00 pm - 9:35 pmORD-PWM
2h 35mnonstop
United Airlines Logo
4:48 pm - 6:49 pmPWM-ORD
3h 01mnonstop
$151United Airlines
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Sat, Aug 16 - Fri, Aug 22
United Airlines Logo
6:30 pm - 10:01 pmORD-PWM
2h 31mnonstop
United Airlines Logo
6:41 pm - 11:25 pmPWM-ORD
5h 44m1 stop
$161United Airlines
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Wed, Sep 3 - Sat, Sep 6
JetBlue Logo
6:10 am - 1:22 pmORD-PWM
6h 12m1 stop
JetBlue Logo
2:17 pm - 6:24 pmPWM-ORD
5h 07m1 stop
$183JetBlue
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Wed, Aug 13 - Wed, Aug 20
JetBlue Logo
12:07 pm - 12:17 amORD-PWM
11h 10m1 stop
JetBlue Logo
6:05 am - 11:18 amPWM-ORD
6h 13m1 stop
$190JetBlue
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Sat, Aug 23 - Sat, Aug 30
Delta Logo
7:05 am - 4:22 pmORD-PWM
8h 17m1 stop
Delta Logo
5:30 pm - 11:56 pmPWM-ORD
7h 26m1 stop
$217Delta
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Sat, Aug 16 - Wed, Aug 20
Delta Logo
3:30 pm - 12:03 amORD-PWM
7h 33m1 stop
Delta Logo
4:50 pm - 10:20 pmPWM-ORD
6h 30m1 stop
$219Delta
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Expert advice

Expert advice for your flight from O'Hare Intl to Portland

 
Snippets provided in this section are AI-generated based on a summarization of KAYAK-commissioned articles. The articles are presented as-is, for general informational purposes only, and may not be up-to-date. The opinions contained in the articles are original to the author and reflect their authentic experience, which may vary significantly from the experience of others.
KAYAK teamed up with top travel experts to share the best tips for your journey.
Airlines
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.

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.

Read more about Frontierby Stefanie Waldek
Our travel experts
Stefanie Waldek

Stefanie Waldek

Expert on United Airlines and Frontier

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
Useful Info

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 Friday. 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 $311 (return) on average. On the other hand, the most expensive months are November and December, where the average cost of round-trip tickets is $519 and $476 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 $552, 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 2 weeks before departure. For the absolute cheapest price, our data suggests you should book 25 weeks before departure.

Good to know

Low seasonFebruary
High seasonAugust
Cheapest flight$66
Best time to beat the crowds but there is an average 15% increase in price.
Most popular time to fly and prices are also 21% 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 $66 for a one-way ticket and $130 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, JetBlue, Delta, and Alaska Airlines 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 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?

    oneworld, and Star Alliance are the airline alliances operating flights between Chicago O'Hare Airport and Portland, with oneworld 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 8.0, Delta is the most popular choice. United Airlines is also a great choice for the route, with an average price of $388 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 $129 or less one-way and $307 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

Air New Zealand, American Airlines, Emirates, +2 more

Air New Zealand, American Airlines, +3 more

Tuesday

Air New Zealand, American Airlines, Emirates, +2 more

Air New Zealand, American Airlines, +3 more

Wednesday

Air New Zealand, American Airlines, Emirates, +2 more

Air New Zealand, American Airlines, +3 more

Thursday

Air New Zealand, American Airlines, Emirates, +2 more

Air New Zealand, American Airlines, +3 more

Friday

Air New Zealand, American Airlines, Emirates, +2 more

Air New Zealand, American Airlines, +3 more

Saturday

Air New Zealand, American Airlines, Emirates, +2 more

Air New Zealand, American Airlines, +3 more

Sunday

Air New Zealand, American Airlines, Emirates, +2 more

Air New Zealand, American Airlines, +3 more

See more direct flights

Direct returns

Portland to Chicago O'Hare Intl

Monday

Air New Zealand, American Airlines, Qatar Airways, +1 more

Air New Zealand, American Airlines, +2 more

Tuesday

Air New Zealand, American Airlines, Qatar Airways, +1 more

Air New Zealand, American Airlines, +2 more

Wednesday

Air New Zealand, American Airlines, Qatar Airways, +1 more

Air New Zealand, American Airlines, +2 more

Thursday

Air New Zealand, American Airlines, Qatar Airways, +1 more

Air New Zealand, American Airlines, +2 more

Friday

Air New Zealand, American Airlines, Qatar Airways, +1 more

Air New Zealand, American Airlines, +2 more

Saturday

Air New Zealand, American Airlines, Qatar Airways, +1 more

Air New Zealand, American Airlines, +2 more

Sunday

Air New Zealand, American Airlines, Qatar Airways, +1 more

Air New Zealand, American Airlines, +2 more

See more direct flights

Reviews of the top 4 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.
8.0
DeltaOverall score based on 7951 reviews
7.3Food
8.5Crew
7.9Comfort
7.9Entertainment
8.2Boarding
Airline reviews

Very late arrival at PWM. Late jet getting to ATL. Equipment problem with aircraft - could not get enough water onto plane., Another delay getting FAA approval for flight with bottled H2O. Not the crew’s problem.

4.0 OkayJames, Jul 2025MSN - ATL
Read more Delta reviews

Very late arrival at PWM. Late jet getting to ATL. Equipment problem with aircraft - could not get enough water onto plane., Another delay getting FAA approval for flight with bottled H2O. Not the crew’s problem.

Everything was fine except the entertainment was not working for half of the flight.

Easy boarding with an extremely kind attendant. Seats were spacious and we had 3 seats for 2 people so we could stretch out. Comfortable air flow and very attentive and hospital attendants. Bathrooms and food were the only negative. Bathrooms were so small you could hardly get in and close the door. I don’t think an obese person would fit or a person with a movement disability. Food was the trending food for flights, nonexistent. We spent $40 getting sandwich and snack at airport for our 6 hour flught.

At first, we were on the runway for about an hour, literally. The Captain did explain that the Control Tower just had a change shift (sounds like an unrealistic excuse) and then that we had to change a runway. A regular economy seat is made for 12 yo twiggy. I understand Delta wants to push for an upgrade, but after sitting in a Comfort seat and in First class. I would say First class is not worthy of my money. The landing was delayed because of the weather in NYC, I don't hold that against Delta, of course. The Captain did alert us to that upon takeoff in Vegas and again as we reached NY.

No one fussed at me about my pap machine as a 3rd pice on the plane. Boarding was pleasant and smooth. The boarding agent in Anchorage was a fun character- he could be in a movie. :~) The on-board crew were downright pleasant. No militant attitudes on Delta. Like all planes these days the seats are too narrow for standard Americans and at 5’2” there is barely enough leg room. I don’t know how tall people fold themselves into the seats. But that’s nothing specific to Delta

My husband upgraded our seats and I don't know if it was due to the type of planet was or if they didn't upgrade our seats. We were supposed to be in I believe comfort seats and they were just as tight as any other seat- no leg room and we are very tall people but at least it wasn't extremely cold. My husband did put in a complaint about our seating because he paid extra and if we would have known that the space and the tightness would have been the same, we just would have gotten the emergency row emergency row seats that we normally get. We love Delta but both our flights coming home we're not good. Oh I forgot to mention that on our flight to Hawaii our luggage wheels got broke and we had to purse new luggage on vacation then we never had this problem so we didn't know protocol and reported it after we got home only for them to tell is we only had 24hrs to report the damage. Not sure what was going on with Delta this vacation trip.

My flight was extremely cold. I had a jacket and a cover was left in each seat. The cover was extremely thin and I have a disability, fibromyalgia and arthrithis and AC air is the worst. I closed my vent and my husbands vent and it still was frigid. I asked the attendant if I could get another cover and she quickly almost dismissively and totally unconcerned stating, (I quote) (one per chair) and walked off so quickly that I didn't get a chance to explain to her that I literally have adisability. I didnt want to make a seen so I set on that flight for over 5 hours in pain, joints locking up and extremely uncomfortable. When my fibromyalgia flares up my joints not only ache but they will lock up also and it takes me days to get back to my regular self even though I take medication for it. I felt like it would not have hurt anyone at all for her to just give me an extra cover because I'm sure they have all types of medical issues in people that fly every day.

After all the weather issues at least they got me to my destination the next day

My flight was canceled after being rescheduled for four days canceling my trip. Kayak and everyone affiliated with it I.e the airlines, and just fly have been excruciating to deal with. My trip to visit family had to be canceled as there was no way to make it. I am furious at all of you.

They delayed our flight because of bad weather in NY which was completely understandable. Then they cancelled our flight and a later flight that evening. The earliest we could fly was the next morning. We ended up buying last minute tickets on another airline and made it home slightly delayed but safely that evening. Delta kept saying it was weather related but if that was the case how did we make it back on another airline? The weather in NY was cloudy but not bad.

It was great, I’m very grateful for the pilots and crew flight attendants for everything.

Evidently, my seat had the only broken TV. I couldn’t plug it in, get it to come on, or watch anything, and of course, no one could fix it while we were on the plane. The service was good and the boarding was quick

I was charged for my daughters bag when I am supposed to receive two free checked bags with my United Explorer card.

The schedule to Moline changed 5 times. The gate changed 6 times. That is a pathetic way to run an airline. No wonder that no one in our company flies on United Express to or from Moline. Changes happen most of the time. I learned my lesson on this trip…never again!

Flight was great. Efficient boarding. Short flight. Early arrival. Friendly flight crew. The entertainment system did not work well. Could not access it until the aircraft reached 10K feet or more. Lots of glitches.

A bit rush for transit. Food and entertainment are not available

Smooth boarding process. Early departure, smooth flight, early arrival. The entertainment package has very good recent movie options. The flight crew were friendly and professional.

My flight was scheduled for about 6:05 departure. There were 11 gate changes from 4-7pm and the flight was 3 hours delayed due to operational issues. The plane taxied around the airport for about half an hour before stopping to be de-iced. It would have been nice if we were alerted of the plan to de-ice prior to the 30 minute drive around the airport. The flight attendant was friendly, which was the only redeeming thing about this flight. As a former flight attendant for United, I was extremely disappointed.

Delays took 2hours and thirty minutes making me miss my connecting flight and make me sit in the Chicago airport for 9 hours

Had a short delay once we boarded the aircraft in Chicago, but it was fixed in no time flat then we were on our way. The pilot was able to make up the time lost and we landed 5 minute later then schedualed . Great service

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.

I have long legs, my foot was out in the aisle and when a flight attendant came walking by and I didn't notice, instead of saying "excuse me" or anything like that, she kicked my foot. Extremely rude

Excellent! The gate agents were kind enough to rebook me on an earlier flight saving me from a 6 hour layover. Even my luggage made it despite the fact that the connection was technically too narrow. The flight itself was very comfortable, roomy, and clean. Plenty of space for my carryon items with plugs to charge my phone. After a long international flight of 14 hours, this was an excellent way to end my travels!

Great experience. Flight boarded easily. Departed early. Smooth flight. Great arrival in DC--almost no taxing! Almost direct to gate from runway. Crew was terrific. Same cookies and beverages in main cabin. I did not use the entertainment system on this flight.

Most of the delay was due to weather which is not what was at issue here. One delay was due to a missing flashlight and in the end the flashlight was actually found on the plane. The entertainment system is very limited. Live TV options offer only a few channels that are not very appealing. Boarding and deplaning are always difficult. It just takes too much time to get on and off the plane. On the plus side, I missed my connecting flight, but was easily able to book a later flight from the app while enroute.

You were more on time than United. I'm so over united delays.

The meals were mediocre and the alcohol selection was poor. I enjoyed the selection of movies and other entertainment.

I chatted with the captain before the flight, and similarly during the welcome announcement, he warned of a turbulent flight that may impact the in-flight service. However, once at altitude, he announced that the weather changed and he immediately turned off the seatbelt sign. But it appeared the cabin crew had already decided to take off this flight. They remained seated and then just chatted in the galley. The flight was fully catered, but only first class received service.

My flight attendant was attentive! The elderly person next to me was flatulent and the flight attendant could see that I was in distress and brought me some face masks

Terrible communication with weather delay, lost baggage, near impossible to reach customer service

My tickets got canceled on me by your site and I didn't have a flight. Then you kept sending me emails on the status of q flight I didn't have tickets for.

The delay was ridiculous because nary a word escaped from the gate attendant regarding our flight status. It was a complete joke.

I missed a flight because of a delay. I had to buy a new ticket through Southwest.

The crew was mostly okay. The flight attendant who answered our questions was curt and unhelpful unfortunately. He seemed upset and I understand having off days.

Flight was delayed one hour. Notification to the crowd waiting near the gate was terrible…announcements were unclear and very hard to hear and therefore understand. Frontier does NOT send texts to notify, only email. The reader board over the gate itself was NEVER updated to indicate the gate had been changed. It’s like a bunch of children are running things.

I’m not gonna fly Frontier Airlines because booking is not an option. No water or food is for high price, not equipped for health emergency incompetent crew for emergency services. Cheap airline shows it is cheaper in all service categories. Boarding is the best of all airlines!

We’ve all seen the YouTube vids of out of control passengers. But this was an instance of a highly aggressive, bully flight attendant. Yelling in the face of a vet with PTSD who was texting their family. And no , we had not yet been instructed to put our phones in airplane mode. My suggestion is that you should pay whatever difference there is in order to avoid Frontier airlines. Additionally, after 3hrs trying to get customer service frontier offered a $25 voucher. I declined. This experience was so traumatic. To be verbally assaulted and abused by a flight attendant that has the power to say “boo” and I miss my flight ( which was to a family member’s funeral ). Frontier is unsafe and I cannot impress enough how much I discourage anyone ( esp those with any kind of disability like PTSD ) flying on Frontier.

My flight was delayed by two hours which made it so that I would miss my layover flight. I stood in line for customer service for over an hour and when I reached the agent she told me to scan a QR code and it'll give me options. I wasn't offered any help, guidance or compensation, only told that I have options but that I had to figure it all out myself. I was refunded part of the trip and had to buy an expensive same day ticket from another airline in order to get home. I will never fly Frontier again.

We were delayed three times ,and that destroyed my plans, and reservations

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

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