PWM - ORD

$96 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 4/7. 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
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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

Fri, Nov 14 - Mon, Nov 17
Delta Logo
4:53 pm - 8:29 pmPWM-ORD
4h 36m1 stop
Delta Logo
8:55 am - 4:07 pmORD-PWM
6h 12m1 stop
$239Delta
Find Deal
Mon, Nov 24 - Thu, Nov 27
United Airlines Logo
6:00 am - 10:45 amPWM-ORD
5h 45m1 stop
United Airlines Logo
10:53 am - 2:12 pmORD-PWM
2h 19mnonstop
$243United Airlines
Find Deal
Fri, Nov 14 - Mon, Nov 17
Delta Logo
4:53 pm - 8:29 pmPWM-ORD
4h 36m1 stop
Delta Logo
11:19 am - 11:19 pmORD-PWM
11h 00m2 stops
$244Delta
Find Deal
Thu, Feb 5 - Sun, Feb 8
United Airlines Logo
4:10 pm - 6:18 pmPWM-ORD
3h 08mnonstop
United Airlines Logo
8:52 am - 2:31 pmORD-PWM
4h 39m1 stop
$247United Airlines
Find Deal
Fri, Dec 5 - Mon, Dec 8
Delta Logo
2:34 pm - 9:39 pmPWM-ORD
8h 05m1 stop
Delta Logo
1:01 pm - 10:23 pmORD-PWM
8h 22m1 stop
$249Delta
Find Deal
Sun, Nov 9 - Thu, Nov 13
Delta Logo
6:00 am - 10:13 amPWM-ORD
5h 13m1 stop
Delta Logo
6:00 am - 4:07 pmORD-PWM
9h 07m2 stops
$254Delta
Find Deal
Thu, Nov 6 - Sun, Nov 9
United Airlines Logo
5:00 pm - 6:55 pmPWM-ORD
2h 55mnonstop
United Airlines Logo
10:53 am - 2:12 pmORD-PWM
2h 19mnonstop
$259United Airlines
Find Deal
Thu, Dec 25 - Thu, Jan 1
American Airlines Logo
12:21 pm - 4:47 pmPWM-ORD
5h 26m1 stop
American Airlines Logo
6:09 am - 11:49 amORD-PWM
4h 40m1 stop
$312American Airlines
Find Deal
Wed, Dec 3 - Wed, Dec 10
Southwest Logo
12:45 pm - 9:50 pmPWM-ORD
10h 05m2 stops
Southwest Logo
6:05 am - 10:15 pmORD-PWM
15h 10m2 stops
$325Southwest
Find Deal
Fri, Dec 12 - Mon, Dec 22
American Airlines Logo
5:17 pm - 9:19 pmPWM-ORD
5h 02m1 stop
American Airlines Logo
5:17 pm - 11:42 pmORD-PWM
5h 25m1 stop
$330American Airlines
Find Deal

Everything you should know

Our travelers' advice
AI-generated summary based on content written by travel experts
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
Delta
Cheapest • from $239 (round-trip)
Delta
Best reviews • 7.9 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
When to book
9 weeks
in advance
Our data shows that travelers who book at least 9 weeks in advance save around 31% compared to booking last minute.
Insights
Insights
Insights
Insights
When to travel
September
Cheapest • 25% price drop
July
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
Cheapest round-trip
$239
Overall average: $386
Delta
Fri 11/14Mon 11/17
PWM - ORD • 1 stop
Cheapest non-stop
$259
Typical prices: $308-$456
United Airlines
Thu 11/6Mon 11/10
PWM - ORD • 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 O'Hare Intl!
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.

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 September, 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 $559 and $452 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.

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 $371 on average.

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 9 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

 
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

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$96
Best time to beat the crowds with an average 0% drop in price.
Most popular time to fly and prices are also 6% 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 $96 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, 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 $377 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 $377 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 $189 or less one-way and $339 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 7997 reviews
7.3Food
8.2Boarding
7.9Entertainment
8.5Crew
7.9Comfort
Airline reviews

The customer service before board was very rude and when I expressed my concerns about making the connecting flight she laughed and told me I bought the wrong ticket. I explained once it showed the flight was delayed it no longer let me change seats or anything. I was trying to upgrade to make sure I would get to the next gate on time.

4.0 OkayHeather, Oct 2025ANC - SEA
Read more Delta reviews

The customer service before board was very rude and when I expressed my concerns about making the connecting flight she laughed and told me I bought the wrong ticket. I explained once it showed the flight was delayed it no longer let me change seats or anything. I was trying to upgrade to make sure I would get to the next gate on time.

Non stop on long haul is the way to go. Great experience

The flight used a B767 with a very old interior from before 2014. The entertainment system did not work at all during the flight despite attempts to reset the system. It was like they flew this route just to be competitive.

They changed planes and the new plane couldn’t carry enough fuel to fly across the country so we had to stop in Kansas City to refuel. Flight was delayed .

Flight was too crowded and seats are too small, especially since passengrs are getting larger. Having a middle seat is ALWAYS tough! Woman on my left was large & kept creeping in to my space. Flight personnel were great! Have more savory rather than sweet snacks please.

Flight was crowded and the woman sitting on my left was large & kept crouching in to my space. You need bigger seats or smaller passengers to fit into the seats you DO have! Snack were OK. Would appreciate if airlines had more savory rather than sweet snacks, thank you!

Delayed flight (1hour) plus a long layover after an overnight flight with no backup plane available.

We were delayed, which I think had to do with air traffic control. Otherwise, everything was great.

The boarding process needs to be refined. Sometimes the gate crew calls out the zones and then flip to showing the.zones boarding on the gate monitor display. So, unless you are huddled around the gate lanes watching the monitor, you could miss your boarding zone. Suggest the zones be announced each time a new zone is allowed to board.

The boarding process needs to be refined. Sometimes the gate crew call out the boarding zone, and then flip to the monitor to show which zones are boarding. So unless everyone is gathered around to see the monitor there is usually confusion as wi which zones are boarding.

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

After boarding the plane in Chicago, the passengers were told that there was a technical problem with the plane. Passengers remained on the plane as they tried to fix the problem. After what was probably an hour passengers were told that there was a need to change planes as the problem was not solved. Passengers disembarked and boarded another plane. After taxing to the runway and waiting for takeoff, passengers were told that owing to the thunderstorm the flight was unable to take off but would try and reroute. After some time passengers were told there wasn't enough fuel for the new route and the plane had to return to the gate for additional fuel. after another log delay the flight got underway. On the plane there was food, drinks, ice or entertainment. We were a glass of water, which appeared rationed. Flight arrived about 5 hours late. The pilot was fantastic and communicated with the passengers throughout the ordeal.

Better WiFi. I cannot understand that in 2025, United is so behind on a technology that is now a necessity and still painfully unreliable, slow and keeps disconnecting.

Trip was great. A wild landing in Ottawa with the wind and rain, but the pilot did a great job. Always love flying United.👍

Excellent experience. Starting with the agent at the Premier bag drop who noticed I was very early for my scheduled flight and offered to rebook me on an earlier flight with my seat preference. She would not let me leave the counter until she knew that all of the changes and new boarding pass showed up on my United app. At the gate, the flight boarded quickly such that we departed early and the flight was smooth. We arrived 20 minutes early at ORD and I was able to be home in time for dinner. One of the best flights I've had.

Salina to travers city was great! But the sept 24 Tranverse city was not! Traverse city to chichago was cancelled, i went to Denver & got to Salina 6 hours later!

See previous note about the passenger in Denver who threw my husband's bag out of the overhead bin in order to maker room for his own. And the flight attendant back up the new passenger.

Flight attendant in first class gave poor service (like he didn't want to be there) and food was awful. We sat waiting for gate upon arrival over 45 mins.

Weather delay in Chicago?. No sense of urgency to make connection in Chicago for our connecting flight that wasn't delayed. Connection was missed.

Overall it was good. I missed my connection but I was put on another 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.

Excellent - explanations were clear staff was nice and flight was comfortable

Lost bag and 2 days no word leaving for cruise no clothes or stuff

Any flight to ORD after about 2pm this summer has been challenging. Flight was delayed getting in (coming from ORD) and that led to it not leaving before a ground stop due to lightening before they could fuel the plane, and so forth. They made up some time but we were still late in arriving at ORD, and that led to missed connections.

Food was ok, but not as good as I have had before on AA.

Pretty good. The food was just mediocre, the boarding and crew were good.

My flight got switched and my prepaid bag didnt transfer over properly so I paid to check ANOTHER BAG. I was placed in a middle seat and it was just miserable. At least it was a bulkhead row so I had legroom. The flight just never seem3d to end

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

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