ORD - PWM

$97 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 6/9. 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
$239
Typical prices: $446-$282
Delta
Sat 5/30Mon 6/1
ORD - PWM • 2 stops
Cheapest non-stop
$242
Typical prices: $429-$283
United Airlines
Tue 8/11Tue 8/18
ORD - PWM • Non-stop
Advice from real travelers
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
Cheapest • from $239 (round-trip)
Best reviews • 7.4 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Nonstop flights
You can fly direct with American Airlines and United Airlines. Average duration is 2h 33m
Direct flights
Direct flights
+1
+1
Direct flights
Direct flights
+1
Avoid delays
Most punctual • 82% on-time
Best time • Fewest delays
Insights
Insights
Insights
Insights
When to book
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
Cheapest • 19% price drop
Most popular
Good to know
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+1
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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!
Flight Deals
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Expert advice
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

Sat, May 30 - Mon, Jun 1
Delta Logo
6:24 am - 4:07 pm
ORD
-
PWM
8h 43m
2 stops
Delta Logo
6:02 am - 4:56 pm
PWM
-
ORD
11h 54m
2 stops
$239Delta
Tue, Aug 11 - Tue, Aug 18
United Airlines Logo
6:25 pm - 10:01 pm
ORD
-
PWM
2h 36mnonstop
United Airlines Logo
6:00 am - 7:55 am
PWM
-
ORD
2h 55mnonstop
$242United Airlines
Tue, Jun 9 - Mon, Jun 15
Delta Logo
8:52 am - 4:00 pm
ORD
-
PWM
6h 08m
1 stop
Delta Logo
11:48 am - 7:31 pm
PWM
-
ORD
8h 43m
1 stop
$243Delta
Fri, May 29 - Sat, May 30
Delta Logo
2:59 pm - 11:09 pm
ORD
-
PWM
7h 10m
1 stop
Delta Logo
11:55 am - 7:09 pm
PWM
-
ORD
8h 14m
1 stop
$247Delta
Tue, Jun 9 - Sat, Jun 13
Delta Logo
2:07 pm - 11:29 pm
ORD
-
PWM
8h 22m
2 stops
Delta Logo
6:15 am - 2:14 pm
PWM
-
ORD
8h 59m
1 stop
$248Delta
Mon, Sep 21 - Wed, Oct 7
United Airlines Logo
6:25 pm - 10:01 pm
ORD
-
PWM
2h 36mnonstop
United Airlines Logo
5:15 am - 11:13 am
PWM
-
ORD
6h 58m
1 stop
$249United Airlines
Wed, May 6 - Wed, May 13
United Airlines Logo
11:00 am - 7:04 pm
ORD
-
PWM
7h 04m
1 stop
United Airlines Logo
6:00 am - 7:56 am
PWM
-
ORD
2h 56mnonstop
$251United Airlines
Fri, May 29 - Sat, May 30
Delta Logo
11:09 am - 11:09 pm
ORD
-
PWM
11h 00m
2 stops
Delta Logo
11:55 am - 7:09 pm
PWM
-
ORD
8h 14m
1 stop
$252Delta
Tue, May 12 - Tue, May 12
United Airlines Logo
7:00 am - 10:28 am
ORD
-
PWM
2h 28mnonstop
United Airlines Logo
4:50 pm - 6:48 pm
PWM
-
ORD
2h 58mnonstop
$253United Airlines
Tue, Jun 9 - Tue, Jun 16
Delta Logo
11:30 am - 11:15 pm
ORD
-
PWM
10h 45m
2 stops
Delta Logo
6:00 am - 4:26 pm
PWM
-
ORD
11h 26m
2 stops
$254Delta
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.

How much is a round-trip flight from Chicago O'Hare Intl Airport to Portland, Maine?

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 O'Hare Intl Airport to Portland, Maine departing in May.

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 March, where tickets cost $301 (return) on average. On the other hand, the most expensive months are December and July, where the average cost of round-trip tickets is $471 and $417 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.

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 $299 on average.

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 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.
Our travel experts
Stefanie Waldek

Stefanie Waldek

Expert on Frontier and United Airlines

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 American 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.

Good to know

Low seasonJanuary
Cheapest flight$97
Best time to beat the crowds but there is an average 2% increase in price.
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 $97 for a one-way ticket and $239 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, Delta, 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 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, United Airlines or American Airlines?

    The two airlines most popular with KAYAK users for flights from Chicago to Portland are United Airlines and American Airlines. With an average price for the route of $371 and an overall rating of 7.4, United Airlines is the most popular choice. American Airlines is also a great choice for the route, with an average price of $350 and an overall rating of 7.1.

  • 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 $174 or less one-way and $340 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 airlines flying 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.
7.4
United AirlinesOverall score based on 9638 reviews
7.3Comfort
8.1Crew
6.6Food
7.7Boarding
7.1Entertainment
Airline reviews

The crew was great. Very friendly and responsive. The plane was old, small and tight. We ran out of overhead space and I had to check. Middle seat was particularly tight.

8.0 ExcellentSally, Apr 2026
ORD - SNA
Read more United Airlines reviews

The crew was great. Very friendly and responsive. The plane was old, small and tight. We ran out of overhead space and I had to check. Middle seat was particularly tight.

Several missed and almost missed connections. It felt like everything was being patched together last minute without enough resources and it ended up being an extremely stressful experience that basically ruined our weekend on the west coast. What a waste.

Crew was friendly. Seats are too narrow, particularly when a big person is in the adjacent seat, but I understand this is due to smaller planes usually flight into Lincoln. I have experienced several flight delays going out and coming into Lincoln airport, I say maybe 50% or higher of the flights I've taken out of this airport have been delayed.

Great flight. Boarded efficiently. Arrived early at CLT. There was no in flight entertainment on this aircraft. Great crew.

The seat was comfortable. There was a lot of turbulence. If it weren't for that,it would have been okay.

Poor communication, flight was delayed for preventable reasons. I missed my connection.

No meal service to the back of the plane as it started late or was too slow to get it out before it was time to land.

Terrible, if possible won't be flying again anytime soon!

Efficient boarding and early departure. Very smooth flight. Early arrival in ATL. Great flight.

Smooth and easy boarding, comfortable for the entire 5 hour flight, and the seat back entertainment was great! I appreciated all the features, from location info and maps, movies, the ability to connect with Bluetooth headphones, and good selection of movies. Food was good, normal airline snacks (I didn’t purchase anything)

Original flight was on time, then late, then changed gates...4 times. Once our newest plane came in, it was fine.

I almost missed my flight and they helped me out enormously

Delays experienced in boarding/take off due to incoming plane delayed. However, the boarding time/depart time in the app was significantly delayed in providing these updates. Usually not updated until an hour after we should have already boarded. Poorly managed.

Moved to earlier flight which unexpectedly had maintenance issues initially indicated as quick fix to ultimately plane changes. Moved back to original flight, also delayed. In all cases customer updates and communication very unclear, no updates on drivers for delays.

Typical AA - late by 90+ mn. Gate changed twice... Changed the departure time 6 times No explanation, no communication on reasons for delay I travel with AA twice a year... and it is consistently very poor.. I will continue to use AA only when i have to.

Pretty awful. 2 hours late due to operational issues and finally deboarded around 2am.

The gate got changed several times and the flight was delayed over an hour. Awful experience

American continues to decline in their customer service and its beyond disappointing.

It was an older plane. First Class was not especially roomy or comfortable. It was a short flight so there were no meal but they did offer mixed nuts which used to be normal but now is rare. Crew member was very polite and professional.

Flight to Tampa was delayed taking off due to plane arriving late but no other issues

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

Information on your arrival and departure airports