PWM - ORD

$115 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 3/10. 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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Everything you should know

Cheapest round-trip
$209
Overall average: $435
United Airlines
Tue 4/7Mon 4/13
PWM - ORD • Non-stop
Cheapest one-way
$115
Typical prices: $204-$315
Delta
Tue 3/10
PWM - ORD • 1 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
Top airlines
United Airlines
Cheapest • from $209 (round-trip)
Delta
Best reviews • 7.9 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
When to book
7 weeks
in advance
Our data shows that travelers who book at least 7 weeks in advance save around 31% compared to booking last minute.
Insights
Insights
Insights
Insights
When to travel
September
Cheapest • 21% 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, Apr 7 - Mon, Apr 13
United Airlines Logo
6:04 am - 8:00 am
PWM
-
ORD
2h 56mnonstop
United Airlines Logo
6:10 pm - 9:40 pm
ORD
-
PWM
2h 30mnonstop
$209United Airlines
Thu, Jun 4 - Sun, Jun 7
United Airlines Logo
7:15 pm - 11:21 pm
PWM
-
ORD
5h 06m
1 stop
United Airlines Logo
6:25 pm - 9:58 pm
ORD
-
PWM
2h 33mnonstop
$219United Airlines
Fri, Feb 27 - Thu, Mar 5
United Airlines Logo
4:15 pm - 6:27 pm
PWM
-
ORD
3h 12mnonstop
United Airlines Logo
11:48 am - 3:14 pm
ORD
-
PWM
2h 26mnonstop
$229United Airlines
Tue, Mar 17 - Sat, Mar 21
American Airlines Logo
6:00 am - 10:57 am
PWM
-
ORD
5h 57m
1 stop
American Airlines Logo
8:02 pm - 11:34 pm
ORD
-
PWM
2h 32mnonstop
$230American Airlines
Thu, Apr 23 - Sun, Apr 26
United Airlines Logo
6:04 am - 8:00 am
PWM
-
ORD
2h 56mnonstop
United Airlines Logo
6:10 pm - 9:40 pm
ORD
-
PWM
2h 30mnonstop
$231United Airlines
Wed, Jul 22 - Tue, Jul 28
Delta Logo
6:50 pm - 11:55 pm
PWM
-
ORD
6h 05m
1 stop
Delta Logo
1:15 pm - 11:59 pm
ORD
-
PWM
9h 44m
2 stops
$234Delta
Sat, Jul 4 - Thu, Jul 9
United Airlines Logo
4:58 pm - 6:58 pm
PWM
-
ORD
3h 00mnonstop
United Airlines Logo
6:25 pm - 9:58 pm
ORD
-
PWM
2h 33mnonstop
$238United Airlines
Thu, Apr 9 - Mon, Apr 13
Delta Logo
12:51 pm - 6:34 pm
PWM
-
ORD
6h 43m
1 stop
Delta Logo
2:25 pm - 11:23 pm
ORD
-
PWM
7h 58m
1 stop
$239Delta
Wed, Jul 8 - Sun, Jul 12
United Airlines Logo
7:15 pm - 11:21 pm
PWM
-
ORD
5h 06m
1 stop
United Airlines Logo
6:25 pm - 9:58 pm
ORD
-
PWM
2h 33mnonstop
$240United Airlines
Fri, Mar 6 - Wed, Mar 11
United Airlines Logo
6:00 am - 12:00 pm
PWM
-
ORD
7h 00m
1 stop
United Airlines Logo
11:48 am - 3:14 pm
ORD
-
PWM
2h 26mnonstop
$242United 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.

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 $509 and $435 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 $323, 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 7 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.
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 seasonJanuary
Cheapest flight$115
Best time to beat the crowds with an average 19% 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, 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?

    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 $371 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 $186 or less one-way and $370 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 8186 reviews
7.8Entertainment
7.9Comfort
7.2Food
8.5Crew
8.1Boarding
Airline reviews

Sorry I didn't realize I was writing a review for each leg. Please see my previous review - it applies to the entire flight, not just a single leg.

2.0 MediocreZachariah, Feb 2026
ATL - TPA
Read more Delta reviews

Sorry I didn't realize I was writing a review for each leg. Please see my previous review - it applies to the entire flight, not just a single leg.

This is the first time I've been disappointed with Delta. I was called by Delta to see if I would volunteer to change flights since my original flight home was overbooked. I accepted. The modified booking only provided me a 35 minute layover - when you subtract the fact that boarding closes for a flight 15 minutes early, that gave me 20 minutes to run for one end of the airport to the other. I barely made it. On the 2.5 hour flight to Tampa, the crew repeatedly let us know over the intercom that they cannot serve drinks or snacks due to safety/turbulence. I would have accepted this reason if they did not CONTINUALLY SERVE DRINKS AND COOKED FOOD to First class. If safety is the excuse then the entire plane should be strapped in for safety. On top of this the air conditioning vents were not working correctly and the plane was uncomfortably warm. I love Delta and am a loyal Delta traveler, and I have never had an experience like this. I don't know if there's a disconnect between availability among third-party sites like KAYAK and the airlines or what, but when overbooking causes issues like this for travelers it should be reviewed and changes to the booking process should be made. I blame BOTH KAYAK and Delta for this terrible experience.

boarded at 5:30 pm, pushed away from gate at 6pm ... takeoff was not until ~6:45pm; disappointing

Smooth boarding, pleasant and professional lady checking us in. Crew service was excellent, again pleasant, but professional. Nice touch-down on landing! Thank you Delta. 💗

Originally, I was booked in economy. I paid several hundred additional dollars to upgrade to first class. Then I paid several more hundred dollars to change my flight to a slightly earlier flight. I asked if the changed flight would also seat me in first class, and I was told that it would. When I boarded the plane, however, I was seated in economy. So, I paid $500-600 more than I paid for my original ticket for an upgrade and a changed flight - received the changed flight (which was nice), but did not receive the upgrade. So, I was not completely satisfied.

Awesome! On time flight, early arrival, and a complimentary upgrade!

Paid for wifi that didn't work. No plug in seat to work. No entertainment.

We departed early and made up time in the air allowing us to arrive 30 minutes early. Capt was incredibly genuine and thanked every passenger for flying with Delta. Completely humble and professional!

Was forced to check in my small carry on, even though I informed the crew it has very fragile items inside

This was one of the worst flights I’ve been on in years. I upgraded to comfort and had such an uncomfortable experience. The person next to me was oversized - which I understand - however, they took up their space and mine. I could only use about 50% of my seat space to not be physically touching this person the entire flight and there was no spatial awareness. I also could not use the seat outlet because their body was obstructing it. It was very inconvenient. Their body kept touching me repeatedly during the flight and I felt very uncomfortable. To pay more for an upgraded space and then not even being able to use it was highly disappointing.

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 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

We flew in first class. The crew did not offer drinks before the flight took off, but they treated us well during the flight. The food was excellent. There was actually too much food served, but it was nice to have all the options.

Update to handle the delay was very bad, crews no smiles or welcome or thanks. Don’t care attitude

Pilot navigated severe weather/snow storm with skill. Described his intentions clearly

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.

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

Information on your arrival and departure airports