CHI - PWM

$102 Find Cheap Flights from Chicago 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 Chicago to Portland departing on 9/23. 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

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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Flight Deals

Cheap Flights from Chicago to Portland (CHI-PWM)

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

Wed, Sep 3 - Sat, Sep 6
American Airlines Logo
10:05 am - 8:11 pmORD-PWM
9h 06m1 stop
American Airlines Logo
8:40 am - 7:01 pmPWM-ORD
11h 21m1 stop
$238American Airlines
Find Deal
Fri, Oct 31 - Sun, Nov 2
American Airlines Logo
7:58 am - 11:28 amORD-PWM
2h 30mnonstop
American Airlines Logo
5:41 am - 10:58 amPWM-ORD
6h 17m1 stop
$239American Airlines
Find Deal
Sat, Oct 18 - Wed, Oct 22
Southwest Logo
11:20 am - 2:30 pmMDW-PWM
2h 10mnonstop
Southwest Logo
7:40 am - 12:00 pmPWM-MDW
5h 20m1 stop
$241Southwest
Find Deal
Sun, Oct 19 - Sat, Oct 25
Southwest Logo
1:30 pm - 4:40 pmMDW-PWM
2h 10mnonstop
Southwest Logo
4:45 pm - 6:20 pmPWM-MDW
2h 35mnonstop
$245Southwest
Find Deal
Thu, Sep 4 - Sat, Sep 6
United Airlines Logo
6:25 pm - 9:59 pmORD-PWM
2h 34mnonstop
United Airlines Logo
6:00 am - 12:57 pmPWM-ORD
7h 57m1 stop
$246United Airlines
Find Deal
Fri, Sep 19 - Thu, Sep 25
JetBlue Logo
1:36 pm - 10:07 pmORD-PWM
7h 31m1 stop
JetBlue Logo
2:17 pm - 8:49 pmPWM-ORD
7h 32m1 stop
$248JetBlue
Find Deal
Wed, Dec 17 - Sat, Jan 10
Delta Logo
9:30 am - 4:10 pmMDW-PWM
5h 40m1 stop
Delta Logo
12:50 pm - 6:34 pmPWM-MDW
6h 44m1 stop
$251Delta
Find Deal
Sat, Oct 11 - Wed, Oct 15
United Airlines Logo
6:10 pm - 9:44 pmORD-PWM
2h 34mnonstop
United Airlines Logo
7:25 pm - 11:15 pmPWM-ORD
4h 50m1 stop
$254United Airlines
Find Deal
Wed, Sep 17 - Wed, Sep 24
Delta Logo
1:22 pm - 12:11 amORD-PWM
9h 49m2 stops
Delta Logo
5:00 pm - 8:20 pmPWM-ORD
4h 20m1 stop
$256Delta
Find Deal
Thu, Sep 4 - Sat, Sep 6
JetBlue Logo
1:36 pm - 10:02 pmORD-PWM
7h 26m1 stop
JetBlue Logo
7:09 am - 6:23 pmPWM-ORD
12h 14m1 stop
$258JetBlue
Find Deal
Expert advice

Expert advice for your flight from Chicago to Portland

 
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

United's Economy Plus offers up to 6 inches more legroom than standard economy seats.


United's Priority Boarding puts you in Zone 2, avoiding overhead bin space issues.

American Airlines

Main Cabin Extra offers early boarding and complimentary alcoholic drinks for a small fee.


Download the American Airlines app for in-flight entertainment on your device.

Frontier

Frontier's Premium Bundle includes priority boarding and extra legroom seats.


Avoid Basic Fare for more flexibility; Economy Bundle offers carry-on and seat choice.

Read more about Frontierby Stefanie Waldek
Our travel experts
Stefanie Waldek

Stefanie Waldek

Expert on United Airlines and Frontier

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
Booking Insights

KAYAK's insights & trends for Chicago to Portland flights

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

What is the cheapest Chicago to Portland flight route?

Data is based on round-trip flight searches on KAYAK over the past month.

The cheapest return flight from Chicago to Portland costs $199 on the route between Chicago Midway Airport (MDW) and Portland (PWM). Over the past month, flights between Chicago O'Hare Intl Airport (ORD) and Portland (PWM) were, on average, 3% cheaper than other Chicago-Portland routes. This is also the most popular route.

What’s the cheapest day of the week to fly from Chicago to Portland?

The average price of all round-trip flights from Chicago 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 Friday. On your return trip to Chicago, you should consider flying back on a Thursday, and avoid Sundays for better deals.

What is the cheapest month to fly from Chicago to Portland?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Chicago 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 to Portland is February, where tickets cost $285 (return) on average. On the other hand, the most expensive months are December and April, where the average cost of round-trip tickets is $464 and $457 respectively.

Can I save money by flying with a layover from Chicago 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 $490 on average.

How far in advance should I book a flight from Chicago 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 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 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 25 weeks before departure.

Good to know

Low seasonFebruary
Cheapest flight$102
Best time to beat the crowds with an average 22% drop in price.
Most popular time to fly and prices are also 7% lower on average.
Flight from Chicago O'Hare Airport to Portland

When to book flights from Chicago to Portland

Are your dates flexible? Find out the best times to travel from Chicago 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 flights from Chicago to Portland

  • What is the cheapest flight from Chicago to Portland?

    In the last 3 days, the lowest price for a flight from Chicago to Portland was $102 for a one-way ticket and $238 for a round-trip.

  • Do I need a passport to fly between Chicago and Portland?

    No, a passport isn't needed to fly from Chicago to Portland. However, local authorities might ask for an official ID.

  • Which airports will I be using when flying from Chicago to Portland?

    There are 2 airports in Chicago (Chicago Midway and Chicago O'Hare Intl.) and only 1 airport in Portland (Portland). The cheapest flights are generally found on the Chicago O'Hare Airport to Portland flight route.

  • Which airlines offer Wi-Fi service onboard planes from Chicago to Portland?

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

  • Which aircraft models fly most regularly from Chicago to Portland?

    The Embraer 175 is the aircraft model that flies most regularly on the Chicago to Portland flight route.

  • Which airline alliances offer flights from Chicago to Portland?

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

  • On which days can I fly direct from Chicago to Portland?

    There are nonstop flights from Chicago to Portland on a daily basis.

  • Which is the best airline for flights from Chicago to Portland, Southwest or Delta?

    The two airlines most popular with KAYAK users for flights from Chicago to Portland are Southwest and Delta. With an average price for the route of $373 and an overall rating of 8.0, Southwest is the most popular choice. Delta is also a great choice for the route, with an average price of $261 and an overall rating of 7.9.

  • How does KAYAK find such low prices on flights from Chicago 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 to Portland.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Portland from Chicago 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 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 with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Chicago 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 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 to Portland

  • Looking for a cheap flight? 25% of our users found flights on this route for $156 or less one-way and $316 or less round-trip.

Prefer to fly direct from Chicago to Portland?

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

Direct departures

Chicago to Portland

Monday

American Airlines, Southwest, United Airlines

American Airlines, Southwest, +1 more

Tuesday

American Airlines, Southwest, United Airlines

American Airlines, Southwest, +1 more

Wednesday

American Airlines, Southwest, United Airlines

American Airlines, Southwest, +1 more

Thursday

American Airlines, Southwest, United Airlines

American Airlines, Southwest, +1 more

Friday

American Airlines, Southwest, United Airlines

American Airlines, Southwest, +1 more

Saturday

American Airlines, Southwest, United Airlines

American Airlines, Southwest, +1 more

Sunday

American Airlines, Southwest, United Airlines

American Airlines, Southwest, +1 more

See more direct flights

Direct returns

Portland to Chicago

Monday

American Airlines, Southwest, United Airlines

American Airlines, Southwest, +1 more

Tuesday

American Airlines, Southwest, United Airlines

American Airlines, Southwest, +1 more

Wednesday

American Airlines, Southwest, United Airlines

American Airlines, Southwest, +1 more

Thursday

American Airlines, Southwest, United Airlines

American Airlines, Southwest, +1 more

Friday

American Airlines, Southwest, United Airlines

American Airlines, Southwest, +1 more

Saturday

American Airlines, Southwest, United Airlines

American Airlines, Southwest, +1 more

Sunday

American Airlines, Southwest, United Airlines

American Airlines, Southwest, +1 more

See more direct flights

Reviews of the top 5 airlines serving from Chicago 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 Chicago 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.
8.0
SouthwestOverall score based on 4246 reviews
7.0Food
8.1Boarding
8.6Crew
7.5Entertainment
8.0Comfort
Airline reviews

Near 4 hour flight with only 1 service. Had to use call button to request water. Internet and power not working until into flight. Internet would stop working during flight.

6.0 GoodDavid, Aug 2025MCO - DEN
Read more Southwest reviews

Near 4 hour flight with only 1 service. Had to use call button to request water. Internet and power not working until into flight. Internet would stop working during flight.

Southwest's seats are the least comfortable I have ever sat in.

The cabin was quiet for the redeye flight. The area was clean. The staff was great. The 787 Max was in good condition. Drawbacks were that the seat widths were tight for some passengers. The seat padding was at best average and for a long flight uncomfortable.

Southwest like most American domestic airlines, is a mediocre airline. But it is among the cheapest. Oh well.

My flight was delayed 50 minutes and we were rushed to board to then sit for 15 minutes until the pilot arrived. Unacceptable since we could have waited to board. Also the delayed flight was updated AFTER we boarded to more than the 10 minutes as originally stated.

Other than a bit of a delay, everything was good. Again, the boarding process and picking seats is the only thing I don't enjoy.

If we are going to have to pay for luggage, make it easier to do. Put something on the app during check-in so I don't need to do it at the kiosk. I've done it twice recently and I ended up having to pay at the desk because something went wrong at the kiosk in Tampa.

Better and more food and drinks. Put msnbc and free speech tv on the news channel selection list.

southwest just starting charging for luggage. hadnt realized it until it was too late. now out $70 when i couldve bought a carry on if i wouldve known. free bags was one of the only reasons i chose southwest over another airline (the other being no assigned seats, which is apparently also being changed). stupid business decision. wont be flying southwest anymore.

The quality of Southwest Airlines continues to degrade each time I fly with them. If it were not for the free luggage, I would probably choose another airline. Their prices are a little bit competitive, but way too high for the quality of the service. Southwest is not unique in this way. Domestic flight in the United States of America has continued to be a lower and lower quality product. Very sad when you compare the quality of domestic airlines to that of many international airlines around the world.

Three seats in first class were broken and while they were able to still acommodate us it was looking very touch and go and they had others they could not acommodate

Mechanic delay in addition to a 2 hour change in takeoff time was frustrating.

Delayed due to thunderstorms and no in-flight service due to rough weather — both of which are out of Delta’s control. Flight was good overall.

The flight attendants in SLC were rude. I arrived 40 minutes early to gate. Ticket said I needed check in for seat assignments and tried check in and attendants said they weren’t doing it. And proceeded to never call me to give me a ticket so when time to board I received the very last seat. Please relay to employees to do their job better..,

On this flight I felt the food offering was not as complete as on previous flights. The tomato salad was a bit off and there was nothing additional such a bread or butter. The breakfast was only one option, so you either ate what they had or ate nothing. The crew was efficient, but most seemed frustrated throughout the flight. The flight arrived early and was obstacle-free, so I’m overall quite happy, but the shine in the rest of the experience just wasn’t there.

The seats got pretty uncomfortable pretty fast. The armrests are bigger than on other planes, so I had less room in the actual seat. My butt hurt by the end of the flight. :/ comfort was the primary issue. The crew were fantastic!

I believe that a four-hour trip should have a meal. Delta had none.

Great flight with Delta! Boarding was quick and easy, the amenities were solid, and the plane was in great shape. The flight attendants had a fun, lively energy while staying professional. All in all, a smooth trip — even managed to catch up on some rest. Thanks, Delta!

I was uncomfortably cold on the plane. Other than that it was uneventful and therefore as enjoyable as a plane ride can be.

There was supposed to be a meal served, but there wasn’t and the major toilet was out of order

Excellent flight. Boarding was efficient and departure was on time. Smooth flight with on time arrival. Deplaning was also efficient.

It was delayed instead of departing at 9:20pm, we departed at 11pm… putting us in Columbus after 2am! It was awful. Had I known about the delay, I could have spent some time in the United Lounge… I was starving because I started my journey in Budapest… so I was exhausted and hungry. Plus I had to make new arrangements to be picked up at the airport in Columbus, instead of midnight it was 2:30 am after getting luggage and out of airport. Not feasible. I would have just stayed in Chicago for the night and gotten a morning flight.

It was great, I’m very grateful for the pilots and crew flight attendants for everything.

Evidently, my seat had the only broken TV. I couldn’t plug it in, get it to come on, or watch anything, and of course, no one could fix it while we were on the plane. The service was good and the boarding was quick

I was charged for my daughters bag when I am supposed to receive two free checked bags with my United Explorer card.

The schedule to Moline changed 5 times. The gate changed 6 times. That is a pathetic way to run an airline. No wonder that no one in our company flies on United Express to or from Moline. Changes happen most of the time. I learned my lesson on this trip…never again!

Flight was great. Efficient boarding. Short flight. Early arrival. Friendly flight crew. The entertainment system did not work well. Could not access it until the aircraft reached 10K feet or more. Lots of glitches.

A bit rush for transit. Food and entertainment are not available

Smooth boarding process. Early departure, smooth flight, early arrival. The entertainment package has very good recent movie options. The flight crew were friendly and professional.

My flight was scheduled for about 6:05 departure. There were 11 gate changes from 4-7pm and the flight was 3 hours delayed due to operational issues. The plane taxied around the airport for about half an hour before stopping to be de-iced. It would have been nice if we were alerted of the plan to de-ice prior to the 30 minute drive around the airport. The flight attendant was friendly, which was the only redeeming thing about this flight. As a former flight attendant for United, I was extremely disappointed.

3 hour weather delay followed by 1 hour (and counting) maintenance delay. UGH!

After we'd boarded , they canceled the flight. The crew didn't even know , we just all received text messages. Then after they deplaned us , AA was just like "too bad, go F your self, we sure ain't gonna help you"

After a two hour delay, my flight was CANCELLED! No pilot available. Such BS.

Amazing food, great staff, with one noticable detail missing ...but no seat entertainment in any of aircraft ...I am not a fan

I wish American Airlines would change the airline industry by loading the plane back to front instead of front to back. Planes would board so much more smoothly and quickly.

I have long legs, my foot was out in the aisle and when a flight attendant came walking by and I didn't notice, instead of saying "excuse me" or anything like that, she kicked my foot. Extremely rude

Excellent! The gate agents were kind enough to rebook me on an earlier flight saving me from a 6 hour layover. Even my luggage made it despite the fact that the connection was technically too narrow. The flight itself was very comfortable, roomy, and clean. Plenty of space for my carryon items with plugs to charge my phone. After a long international flight of 14 hours, this was an excellent way to end my travels!

Great experience. Flight boarded easily. Departed early. Smooth flight. Great arrival in DC--almost no taxing! Almost direct to gate from runway. Crew was terrific. Same cookies and beverages in main cabin. I did not use the entertainment system on this flight.

Most of the delay was due to weather which is not what was at issue here. One delay was due to a missing flashlight and in the end the flashlight was actually found on the plane. The entertainment system is very limited. Live TV options offer only a few channels that are not very appealing. Boarding and deplaning are always difficult. It just takes too much time to get on and off the plane. On the plus side, I missed my connecting flight, but was easily able to book a later flight from the app while enroute.

You were more on time than United. I'm so over united delays.

It was great. I had never flown on JetBlue before, but would be very happy to fly with them in the future.

Worst flight experience ever flights canceled. JetBlue told us just did not even bother standing in line to come back in one and a half hours then without any information we had to go pick up all of our luggage and spend over $2000 in accommodation just to get home. JetBlue said that the next flight available for us to get home would be three days later. Absolutely absurd hasn’t offered to give us any compensation do not fly JetBlue horrible company. They said it was based on the weather and the weather is great in all locations that we would’ve been flying to total hoax. I think it’s a conspiracy theory.

The captain gave good announcements and the flight attendants were friendly. The WiFi was pretty good. The plane itself looked very old inside and the seats were very uncomfortable. The screens in the seat backs were the smallest I’ve ever seen. There were so many loud and obnoxious kids on this flight and the parents didn’t do much to try to quiet them down. Some had videos and games on tablets with higher than necessary volume going the whole time.

Too many long delays with JetBlue. Worst major airline that serves JFK but unfortunately I keep going back because of the prices.

My JetBlue experience was nice. The flights ran on time, the aircraft was clean and comfortable, and the flight attendants were attentive. My only issue, which is isolated to the low-cost (budget) option at JetBlue, is that the check in process makes the user feel that they have to buy their seats. The seats offered for purchase are upgrades from the budget seats you get (which are essentially the last seats remaining). The interface should not make it feel like you must purchase a seat.

The plane was late to leave.. Internet was lousy. TV was not working. when we arrived, We stayed on the plane for a long time before we got to the gate. It took us a long time to retrieve our luggage because they didn’t know what carousel to send them to. It was a bad experience.

I especially liked the lead crew officer. His boarding and safety announcements were made with a bit of novelty and humor. The flight also left the gate 10 minutes early and we landed about 20 minutes early… It was a delightful flight…

There were mutliple delays. There was inconsistent, delayed, and poor communication regarding the delays.

Spend hours delayed with no food, water anything sitting on the aieplane with no ability to eat or use the restroom. My entire experience was the absolute worst. I will never fly jet Blue again.

It would have been nice if they had offered more than one set of snacks

Everything you need to know for your flight from Chicago to Portland

Information on your arrival and departure airports

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