PWM - ORD

$116 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 2/21. 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
41.299.237 searches in the past 7 days on KAYAK

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Filter your dealsChoose cabin class, free Wi-Fi and more.

Everything you should know

Cheapest round-trip
$209
Typical prices: $253-$472
United Airlines
Tue 2/3Tue 2/24
PWM - ORD • Non-stop
Cheapest one-way
$116
Typical prices: $182-$256
United Airlines
Sat 2/21
PWM - ORD • Non-stop
Our travelers' advice
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
When to book
6 weeks
in advance
Our data shows that travelers who book at least 6 weeks in advance save around 31% compared to booking last minute.
Insights
Insights
Insights
Insights
When to travel
January
Cheapest • 22% price drop
July
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

Tue, Feb 3 - Tue, Feb 24
United Airlines Logo
4:10 pm - 6:18 pm
PWM
-
ORD
3h 08mnonstop
United Airlines Logo
11:48 am - 3:14 pm
ORD
-
PWM
2h 26mnonstop
$209United Airlines
Tue, Feb 3 - Tue, Feb 24
United Airlines Logo
4:10 pm - 6:18 pm
PWM
-
ORD
3h 08mnonstop
United Airlines Logo
4:10 pm - 11:20 pm
ORD
-
PWM
6h 10m
1 stop
$219United Airlines
Tue, Feb 3 - Tue, Feb 24
United Airlines Logo
6:00 am - 12:05 pm
PWM
-
ORD
7h 05m
1 stop
United Airlines Logo
8:50 am - 2:23 pm
ORD
-
PWM
4h 33m
1 stop
$229United Airlines
Sat, Feb 14 - Tue, Feb 17
American Airlines Logo
6:49 pm - 10:46 pm
PWM
-
ORD
4h 57m
1 stop
American Airlines Logo
1:45 pm - 5:07 pm
ORD
-
PWM
2h 22mnonstop
$230American Airlines
Sat, Feb 28 - Mon, Mar 2
American Airlines Logo
5:57 pm - 8:07 pm
PWM
-
ORD
3h 10mnonstop
American Airlines Logo
1:45 pm - 5:07 pm
ORD
-
PWM
2h 22mnonstop
$231American Airlines
Fri, Feb 6 - Mon, Feb 9
United Airlines Logo
4:10 pm - 6:18 pm
PWM
-
ORD
3h 08mnonstop
United Airlines Logo
11:00 am - 2:39 pm
ORD
-
PWM
2h 39mnonstop
$233United Airlines
Sat, Feb 7 - Mon, Feb 9
Delta Logo
6:17 am - 5:55 pm
PWM
-
ORD
12h 38m
2 stops
Delta Logo
5:40 pm - 11:22 pm
ORD
-
PWM
4h 42m
1 stop
$234Delta
Mon, Feb 9 - Mon, Feb 16
American Airlines Logo
6:00 am - 12:35 pm
PWM
-
ORD
7h 35m
1 stop
American Airlines Logo
1:45 pm - 5:07 pm
ORD
-
PWM
2h 22mnonstop
$239American Airlines
Tue, Feb 10 - Sun, Feb 15
Delta Logo
6:17 am - 1:14 pm
PWM
-
ORD
7h 57m
1 stop
Delta Logo
6:25 pm - 12:18 am
ORD
-
PWM
4h 53m
1 stop
$249Delta
Tue, Feb 3 - Tue, Feb 24
American Airlines Logo
7:00 am - 1:22 pm
PWM
-
ORD
7h 22m
1 stop
American Airlines Logo
1:45 pm - 5:07 pm
ORD
-
PWM
2h 22mnonstop
$250American Airlines
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 February.

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 Thursday, 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 Thursdays 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 January, where tickets cost $279 (return) on average. On the other hand, the most expensive months are December and April, where the average cost of round-trip tickets is $509 and $457 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 $279, 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 6 weeks before departure, which saves you about 31% 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.
Airlines
United Airlines

Purchase Priority Boarding to ensure overhead bin space for your carry-on.


Check United's Wi-Fi coverage map before purchasing Wi-Fi for consistent connectivity.

American Airlines

Consider Main Cabin Extra for early boarding and complimentary drinks on short flights.


Download the American Airlines app for access to inflight entertainment on domestic flights.

Our travel experts
Stefanie Waldek

Stefanie Waldek

Expert on 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$116
Best time to beat the crowds with an average 3% drop in price.
Most popular time to fly and prices are also 2% lower on average.
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 $115 for a one-way ticket and $209 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, Delta, and JetBlue 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?

    SkyTeam, oneworld, and Star Alliance are the airline alliances operating flights between Portland and Chicago O'Hare Airport, with SkyTeam 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, Delta or United Airlines?

    The two airlines most popular with KAYAK users for flights from Portland to Chicago are Delta and United Airlines. With an average price for the route of $373 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 $373 and an overall rating of 7.4.

  • 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 $216 or less one-way and $337 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 3 airlines serving 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.
7.9
DeltaOverall score based on 8040 reviews
7.9Comfort
8.5Crew
8.1Boarding
7.2Food
7.8Entertainment
Airline reviews

I have diamond medallion status and usually we are in comfort plus . We were in main this time ( which was fine ) and my husband wanted wine . I have at least 10 vouchers for drinks that are good for this year and next! The attendant would not take the picture of the voucher as proof and never came back to check as She asked me to pull it up on delta Wi-Fi. Instead my husband just used his Amex to buy the wine . Disappointing!!!

10.0 ExcellentAnne, Jan 2026
MCO - DTW
Read more Delta reviews

I have diamond medallion status and usually we are in comfort plus . We were in main this time ( which was fine ) and my husband wanted wine . I have at least 10 vouchers for drinks that are good for this year and next! The attendant would not take the picture of the voucher as proof and never came back to check as She asked me to pull it up on delta Wi-Fi. Instead my husband just used his Amex to buy the wine . Disappointing!!!

Food is basically Sun Chips, cookies or Cheezits. I had an exit row seat so I had plenty of room. The crew was very nice and efficient. Pilot kept us informed. Pretty good flight.

Air travel sucks. It continues to be awful for all airlines. No shame on delta alone.

It was Delta, but the flight attendants were stressful and disrespectful. I am a diamond member a travel weekly. I have not had a negative thing to share in quite some time. But this was noticeable.

Comfort Plus seat 11E seemed smaller than prior flights. The movie selection is good. Watched most of the most recent Tron movie. I'll watch the remaining part later as my movie is saved in the Delta Seatback Experience.

Flight was late from Newark to Atlanta, I asked flight attendant to please let my family of 3 out first when we landed to Atlanta because we were late for our connecting flight to Quito. She didn't and we were late for 5 minutes we couldn't board the plane and spend hours trying to get another flight with customer service for the next day.

I really liked the legroom. I am 6’4”.a at For some reason our seats were not together and using the app to fix it didn’t work. Passengers were nice enough to move for us but you should absolutely ensure a parent sits with their child.

Late delayed flight delays boarding and delays leaving and delays on arrival too. Cramped plane no room no food.

DTW line is too long. The flights from DTW to BWI are always delayed for unknown reasons.

Delta canceled our flight and we had to scramble to find another airline to get home. Phoenix is not a delta hub so they didn’t have another plane. It would have been a red eye though Salt Lake City. Getting in at 5am. No bueno.

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

The flights were on time which was great give. It was holiday travel season and there’d been some weather issues. The only complaint and this is every time with United is the terrible seat design. The head rest is not built for comfort and having my neck bent forward for a cross country trip reminded me while I try not to take United flights as a rule.

Everything was absolutely wonderful from check in to baggage claim. Staff was very professional and sweet. Will definitely recommend United to family and friends.

They did the one thing that really matters - got to Chicago early.

The flight was on time. I generally don’t drink or eat on short flights and the seats were good and the flight attendants were friendly. That’s all I expect

It was nice to have gotten up upgraded to first class with a meal on a three hour flight

Very bad! They kept delaying my flight and wouldn’t do anything about it

Door to door, the crew and staff were amazing. It was a stressful travel day with delays, but they were focused on customers and doing what they could to get us to our destinations.

Flight was delayed only slightly before takeoff due to traffic control. However, the flight arrived early to ORD. Good flight. United has been very reliable for me.

Another delayed flight. When the delays exceed the duration of the flight, it’s a problem.

Little warm on the plane and delayed for an hour

So excited very proud first of all I wanna thank kayak all updates very professional and fast alart And amazing cabin crew so nice to me they deserve big salute

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.

Awful. They won’t help me with anything. I booked on American but they abdicated to Iberia. The ticket was overpriced. Everything negative

I enjoyed the extra leg room compared to other airlines. The first stewards made my daughter’s birthday special by giving her an extra snack. Then the last one coming home from Chicago to Appleton made our night really enjoyable Thanks for making our trip enjoyable

It was good..clean, comfy seat. Friendly warm welcoming crew. Was able to check my cabin luggage at the gate which I was able to pickup in a decent time from baggage claim. The app gave all updates from delays to baggage claim info. Overall smooth flight.

It was a typical flight. We had a delay which seems to be the normality now. And we had no in flight service due to conditions.

After we landed we sat on the tarmac for 1.5 hours waiting to get to our gate. Ridiculous.

Terrible. Flight delayed for more than 8 hours with only a $12 meal voucher provided for the inconvenience. The airplane did not have breaks on arrival yet they still made us go through the motions and board on time knowing we could not take off then sit for 40+ minutes before having to get of the time. A complete waste of my time. I cannot believe they can stay business with these shenanigans. I’ll avoid this company like the plague moving forward as the lack of accountability is disgraceful.

This was the best 2 flights I have had with American out of SGF. Great crew both flights.

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

Information on your arrival and departure airports