PWM - ORD

$107 Find Cheap Flights from Portland to Chicago O'Hare Airport

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Portland to O'Hare Intl departing on 5/27. 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 Chicago O'Hare Intl Airport

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

Cheapest round-trip
$239
Typical prices: $401-$283
JetBlue
Sat 6/13Tue 6/16
PWM - ORD • 1 stop
Cheapest non-stop
$269
Typical prices: $437-$279
United Airlines
Fri 5/22Sun 5/24
PWM - ORD • Non-stop
Advice from real travelers
AI-powered summary based on content written by travel experts. AI can make mistakes.
Choose Main Cabin Extra on American for early boarding.
United's Priority Boarding helps secure carry-on space.
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 3h 03m
Direct flights
Direct flights
+1
+1
Direct flights
Direct flights
+1
Top layover airports
Cheapest • Avg $278 (round-trip)
Shortest trip • 4h 59m (one-way)
Insights
Insights
Insights
Insights
When to book
in advance
Our data shows that travelers who book at least 5 weeks in advance save around 30% compared to booking last minute.
Insights
Insights
Insights
Insights
When to travel
Cheapest • 18% price drop
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
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 O'Hare Intl!
Flight Deals
Booking Insights
Expert advice
Flight Deals

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

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

Sat, Jun 13 - Tue, Jun 16
JetBlue Logo
2:30 pm - 9:30 pm
PWM
-
ORD
8h 00m
1 stop
JetBlue Logo
6:00 am - 12:30 pm
ORD
-
PWM
5h 30m
1 stop
$239JetBlue
Sat, Jun 13 - Wed, Jun 17
JetBlue Logo
2:30 pm - 9:30 pm
PWM
-
ORD
8h 00m
1 stop
JetBlue Logo
6:00 am - 1:35 pm
ORD
-
PWM
6h 35m
1 stop
$251JetBlue
Fri, Jun 26 - Tue, Jun 30
JetBlue Logo
2:30 pm - 9:30 pm
PWM
-
ORD
8h 00m
1 stop
JetBlue Logo
6:00 am - 12:30 pm
ORD
-
PWM
5h 30m
1 stop
$268JetBlue
Fri, May 22 - Sun, May 24
United Airlines Logo
4:51 pm - 6:51 pm
PWM
-
ORD
3h 00mnonstop
United Airlines Logo
10:55 am - 2:26 pm
ORD
-
PWM
2h 31mnonstop
$269United Airlines
Fri, Aug 21 - Wed, Aug 26
American Airlines Logo
6:15 am - 8:16 am
PWM
-
ORD
3h 01mnonstop
American Airlines Logo
11:30 am - 3:00 pm
ORD
-
PWM
2h 30mnonstop
$278American Airlines
Fri, May 22 - Sun, May 24
United Airlines Logo
6:00 am - 8:00 am
PWM
-
ORD
3h 00mnonstop
United Airlines Logo
1:18 pm - 7:27 pm
ORD
-
PWM
5h 09m
1 stop
$279United Airlines
Wed, Jul 22 - Tue, Jul 28
JetBlue Logo
2:40 pm - 9:55 pm
PWM
-
ORD
8h 15m
1 stop
JetBlue Logo
6:00 am - 12:21 pm
ORD
-
PWM
5h 21m
1 stop
$284JetBlue
Fri, Aug 21 - Wed, Aug 26
American Airlines Logo
6:15 am - 8:16 am
PWM
-
ORD
3h 01mnonstop
American Airlines Logo
5:20 am - 11:12 am
ORD
-
PWM
4h 52m
1 stop
$288American Airlines
Fri, May 22 - Mon, May 25
American Airlines Logo
5:57 pm - 11:59 pm
PWM
-
ORD
7h 02m
1 stop
American Airlines Logo
6:55 am - 1:38 pm
ORD
-
PWM
5h 43m
1 stop
$289American Airlines
Wed, Jul 22 - Tue, Jul 28
Delta Logo
6:57 pm - 11:53 pm
PWM
-
ORD
5h 56m
1 stop
Delta Logo
2:07 pm - 12:59 am
ORD
-
PWM
9h 52m
2 stops
$294Delta
Booking Insights

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

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

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

This analysis is based on the cheapest round-trip price found on KAYAK in the last 12 months by searching for a flight from Portland, Maine to Chicago O'Hare Intl Airport departing in June.

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

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

If your flying dates are flexible, you should consider flying to Chicago O'Hare Airport on a Wednesday, as we generally find the cheapest rates on that day for this route. On the other hand, Sunday is the most expensive day to fly from Portland to Chicago O'Hare Airport. For your return ticket, we recommend flying on a Tuesday and avoiding Sundays for the best deals.

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

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Portland to Chicago O'Hare Intl Airport, 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 Portland to Chicago O'Hare Intl Airport is September, where tickets cost $279 (return) on average. On the other hand, the most expensive months are December and February, where the average cost of round-trip tickets is $509 and $367 respectively.

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

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 $324, prices are generally cheapest when you fly direct.

How far in advance should I book a flight from Portland to Chicago O'Hare Intl Airport?

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from Portland to Chicago O'Hare Intl Airport, 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 Portland to Chicago O'Hare Intl Airport, you should book around 5 weeks before departure, which saves you about 30% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 26 weeks before departure.

Expert advice

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

 
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

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 seasonFebruary
Cheapest flight$107
Best time to beat the crowds but there is an average 7% increase in price.
Most popular time to fly with an average 2% increase in price.
Flight from Portland to Chicago O'Hare Airport

When to book flights from Portland to O'Hare Intl

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

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

    In the last 3 days, the lowest price for a flight from Portland to Chicago O'Hare Intl Airport was $107 for a one-way ticket and $239 for a round-trip.

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

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

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

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

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

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

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

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

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

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

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

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

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

    The two airlines most popular with KAYAK users for flights from Portland to Chicago are United Airlines and American Airlines. With an average price for the route of $354 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 $304 and an overall rating of 7.1.

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

    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 Portland to Chicago O'Hare Airport.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago O'Hare Airport from Portland 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 Portland to Chicago O'Hare Airport?

    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 Chicago O'Hare Airport with an airline and back to Portland with another airline. Booking your flights between Portland and ORD 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 Portland to Chicago O'Hare Airport?

    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 Chicago O'Hare Airport from Portland 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 Portland to Chicago O'Hare Intl Airport

  • Looking for a cheap flight? 25% of our users found flights on this route for $189 or less one-way and $355 or less round-trip.

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

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

Direct departures

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

Direct returns

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

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

 
See real verified KAYAK customer reviews for airlines flying from Portland to Chicago. 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 Portland to O'Hare Intl? 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 9533 reviews
8.1Crew
6.6Food
7.3Comfort
7.7Boarding
7.1Entertainment
Airline reviews

Just a bad day to fly. Flight was delayed from scheduled 6:50 pm departure to 8:50 pm. Combination of factors mostly related to weather at the destination airport (which is where the incoming flight originated) which delayed the inbound flight over an hour. Once on board, we taxied but had to hold again on the taxiway for 10 minutes or so. We did not get wheels up until after 9 pm. The flight was smooth but about 18 minutes from our destination, we had to hold for several minutes more due to weather at ORD. We finally landed at ORD about 11:08 pm (accounting for the time difference, that was about a 3 hour delay from our scheduled departure time). It felt like we were never going to get to our destination. But the flight crew and attendants were very good. The movie selection onboard was also very nice. Got to watch half of a movie just during our taxi from the gate at ATL due to the delay!

2.0 MediocreDr. Joseph, Apr 2026
ATL - ORD
Read more United Airlines reviews

Just a bad day to fly. Flight was delayed from scheduled 6:50 pm departure to 8:50 pm. Combination of factors mostly related to weather at the destination airport (which is where the incoming flight originated) which delayed the inbound flight over an hour. Once on board, we taxied but had to hold again on the taxiway for 10 minutes or so. We did not get wheels up until after 9 pm. The flight was smooth but about 18 minutes from our destination, we had to hold for several minutes more due to weather at ORD. We finally landed at ORD about 11:08 pm (accounting for the time difference, that was about a 3 hour delay from our scheduled departure time). It felt like we were never going to get to our destination. But the flight crew and attendants were very good. The movie selection onboard was also very nice. Got to watch half of a movie just during our taxi from the gate at ATL due to the delay!

3 hour delay…. Nearly 2 hours sitting on tarmac. Do better, United. Or at least have the sense to not say “we hope you enjoyed your flight with us” upon disembarking.

Flights were on time. Free Wifi on plane. Everything was well organized.

Economy plus was so cramped I could not use my laptop. It was beyond bad.

Wonderful. Quick boarding. Early departure and we arrived 30 minutes early at our destination. Unfortunately, when you arrive early, there is still a departing aircraft at our gate. We had to park for 30 minutes until the gate was clear. So our early arrival was not really early at the gate. Otherwise it was a quick and smooth flight. Appreciated the efficiency.

Crew was great (professional, attentive, prompt). Snacks for 4 hrs flight is deplorable.

United Airlines is my preferred airlines and I am thankful for Gary who also help support me on the phone to switch my flight literally last min.

Seated dude next to me even though lots of empty rows. But main thing was we sat on the tarmac after landing for 30 minutes because of, in the words of the dude who sat next to me, “operational incompetence”. We got changing directions about where to pick up gate checked bags. Pilot and flight attendant were awesome though.

It was a pretty standard flight... until the almost hour and a half spent on the taxi way. I get that the weather has been poor but the delay had nothing to do with the weather and more to do with a plane with several issues tying up the gate. I get that that happens from time to time but this has been EVERY flight I've been on for the past 5 years and I fly 3 to 5 times a year. This isn't just United... it's American, it's Delta. It's an issue with the entire industry. I work for UPS and packages on a cargo plane get better service than people do these days. Anymore I HATE flying.

Perfect flight. Smooth flight. Arrived 20 minutes early at destination. Excellent service.

The staff are very, very professional. It's what flying should feel like.

Flight was delayed half hour before boarding, but when I checked flight aware the plane that would Pick us up had a delay of more than an hour. AA should let us know in advance to avoid waiting several hours in the airport

Delays with no explanation. It could have been handled better.

Jill was the flight attendant in first class she was fabulous!! Best flight attendant I have had in years.!! And I fly every other week. Other can learn from her!!

As a first class customer, there was no power the entire flight which limited my ability to work. I find this unacceptable. The first 11 rows on the left side of the plan were out. I was only offered the option to charge my phone which was not the issue because my laptop was out of power. I asked if there was anything that can be done for me, and the answer was, "no". I was not offered any type of compensation for this AA problem which caused me unnecessary stress due to inability to address business issues on an already challenging travel day. Flight attendants tried to reset the power once but that was the extent of their support. Very disappointing for the lack of expected services on a flight. Please contact me with customer focused response to this complaint.

There was no inflight service. Once we landed we were delayed to find a gate for an hour and a half which was 1/2 the total time in the air.

The chicken wrap was tiny ($13 for what looked like a 1/3 of a normal wrap?) and disgusting.

It was good experience this time. The flight was on time.

There was a delay with the plan which cause the flight to leave later and once arrived in Chicago there was another delay and some passengers missed their connecting flights

The gate agent had a really bad attitude and refused to help me get on the standby list. She just handed me a card and said I needed to call a number. I asked her to help with the AA app on my phone and she just shrugged and said she didnt know. After a few phone calls, I eventually just went to a different gate agent on the other side of the terminal and got the help I needed.

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

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