ORD - PWM

$67 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 10/25. 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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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, Oct 1 - Fri, Oct 3
United Airlines Logo
2:20 pm - 11:13 pmORD-PWM
7h 53m1 stop
United Airlines Logo
6:25 pm - 8:25 pmPWM-ORD
3h 00mnonstop
$245United Airlines
Find Deal
Tue, Dec 16 - Tue, Jan 13
Southwest Logo
11:55 am - 10:15 pmORD-PWM
9h 20m2 stops
Southwest Logo
12:45 pm - 9:50 pmPWM-ORD
10h 05m2 stops
$247Southwest
Find Deal
Thu, Nov 6 - Sun, Nov 9
Delta Logo
7:10 am - 12:00 pmORD-PWM
3h 50m1 stop
Delta Logo
4:53 pm - 8:29 pmPWM-ORD
4h 36m1 stop
$248Delta
Find Deal
Sat, Oct 18 - Tue, Oct 21
American Airlines Logo
6:45 am - 5:38 pmORD-PWM
9h 53m1 stop
American Airlines Logo
6:00 am - 11:06 amPWM-ORD
6h 06m1 stop
$250American Airlines
Find Deal
Tue, Jan 6 - Sat, Jan 10
Delta Logo
2:45 pm - 9:59 pmORD-PWM
6h 14m1 stop
Delta Logo
1:15 pm - 7:25 pmPWM-ORD
7h 10m1 stop
$251Delta
Find Deal
Wed, Oct 1 - Wed, Oct 8
Delta Logo
6:28 pm - 12:34 amORD-PWM
5h 06m1 stop
Delta Logo
6:00 am - 4:11 pmPWM-ORD
11h 11m2 stops
$253Delta
Find Deal
Thu, Oct 2 - Fri, Oct 3
JetBlue Logo
1:35 pm - 10:07 pmORD-PWM
7h 32m1 stop
JetBlue Logo
2:17 pm - 8:49 pmPWM-ORD
7h 32m1 stop
$260JetBlue
Find Deal
Fri, Oct 24 - Tue, Oct 28
American Airlines Logo
7:10 pm - 10:45 pmORD-PWM
2h 35mnonstop
American Airlines Logo
3:28 pm - 5:24 pmPWM-ORD
2h 56mnonstop
$262American Airlines
Find Deal
Thu, Oct 2 - Thu, Oct 16
JetBlue Logo
1:35 pm - 10:07 pmORD-PWM
7h 32m1 stop
JetBlue Logo
7:09 am - 12:23 pmPWM-ORD
6h 14m1 stop
$266JetBlue
Find Deal
Fri, Oct 24 - Sun, Oct 26
 Logo
2:41 pm - 10:41 amORD-PWM
19h 00m1 stop
 Logo
5:40 pm - 8:16 amPWM-ORD
15h 36m1 stop

Everything you should know

Our travelers' advice
AI-generated summary based on content written by travel experts
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 $245 (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 24% compared to booking last minute.
Insights
Insights
Insights
Insights
When to travel
August
Cheapest • 15% price drop
September
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
Cheapest round-trip
$245
Overall average: $344
United Airlines
Wed 10/1Fri 10/3
ORD - PWM • 1 stop
Cheapest non-stop
$255
Typical prices: $469-780
American Airlines
Mon 11/10Wed 11/12
ORD - PWM • Non-stop
Start a new search
KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to Portland!
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
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
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
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 August, where tickets cost $341 (return) on average. On the other hand, the most expensive months are November and December, where the average cost of round-trip tickets is $516 and $483 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 $332, 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 24% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 25 weeks before departure.

Good to know

Low seasonFebruary
Cheapest flight$67
Best time to beat the crowds but there is an average 12% increase in price.
Most popular time to fly and prices are also 15% 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 $67 for a one-way ticket and $245 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 7.9, Delta is the most popular choice. United Airlines is also a great choice for the route, with an average price of $387 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 $194 or less one-way and $272 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 7960 reviews
7.3Food
8.2Boarding
7.9Comfort
8.5Crew
7.9Entertainment
Airline reviews

Perfect flight both ways. On time, courteous staff, plane comfortable and cool. Best domestic flights I’ve had in awhile.

10.0 ExcellentAnonymous, Sep 2025CLT - BOS
Read more Delta reviews

Perfect flight both ways. On time, courteous staff, plane comfortable and cool. Best domestic flights I’ve had in awhile.

Really low quality food especially for an international flight. The crew also was surprisingly unpleasant except couple of ladies. I know we were not in first class but that’s no reason to treat customers as less.

Flight delayed for two and half hours and then canceled altogether due to mechanical issues. No mechanic onsite to fix so had to send one from LAX.

Crew was good. The reservation got mixed up and they didn't have my TSA number. I am also a Silver Medallion and wasn't able to use Sky Priority.

Delta made it easy, comfortable and timely. The crew was fantastic.

This route with Delta always has delays or is cancelled. Aircrafts seem smaller and older. I fly Delta quite a bit - haven’t had issues with the international flights. But this route has always been the troublesome one

Three seats in first class were broken and while they were able to still acommodate us it was looking very touch and go and they had others they could not acommodate

Mechanic delay in addition to a 2 hour change in takeoff time was frustrating.

Delayed due to thunderstorms and no in-flight service due to rough weather — both of which are out of Delta’s control. Flight was good overall.

The flight attendants in SLC were rude. I arrived 40 minutes early to gate. Ticket said I needed check in for seat assignments and tried check in and attendants said they weren’t doing it. And proceeded to never call me to give me a ticket so when time to board I received the very last seat. Please relay to employees to do their job better..,

Once we got in the air the pilot made up some of the time of the delay. So that was really nice.

Excellent flight. Boarding was efficient and departure was on time. Smooth flight with on time arrival. Deplaning was also efficient.

It was delayed instead of departing at 9:20pm, we departed at 11pm… putting us in Columbus after 2am! It was awful. Had I known about the delay, I could have spent some time in the United Lounge… I was starving because I started my journey in Budapest… so I was exhausted and hungry. Plus I had to make new arrangements to be picked up at the airport in Columbus, instead of midnight it was 2:30 am after getting luggage and out of airport. Not feasible. I would have just stayed in Chicago for the night and gotten a morning flight.

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.

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.

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.

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

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