CHI - PWM

$105 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 5/25. 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 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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41,299,237 searches in the past 7 days on KAYAK

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Everything you should know

Cheapest round-trip
$197
Overall average: $299
Delta
Tue 4/21Wed 4/29
ORD - PWM • 1 stop
Cheapest non-stop
$209
Typical prices: $228-$359
United Airlines
Fri 4/10Mon 4/13
ORD - PWM • Non-stop
Advice from real travelers
AI-powered summary based on content written by travel experts. AI can make mistakes.
United's Economy Plus offers extra legroom on this route.
Frontier's Premium Bundle includes priority boarding.
Expert advice
Expert advice
Expert advice
Expert advice
Top airlines
Delta
Cheapest • from $197 (round-trip)
Southwest
Best reviews • 8.0 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Nonstop flights
Every day
You can fly direct with American Airlines and United Airlines. Average duration is 2h 27m
Direct flights
Direct flights
+1
+1
Direct flights
Direct flights
+1
Top routes
ORD
-
PWM
Cheapest • 30% average savings
ORD
-
PWM
Most popular
Insights
Insights
Insights
Insights
Avoid delays
Southwest
Most punctual • 92% on-time
Morning flights
Best time • Fewest delays
Insights
Insights
Insights
Insights
Top layover airports
Detroit (DTW)
Cheapest • Avg $228 (round-trip)
Detroit (DTW)
Shortest trip • 4h 10m (one-way)
Insights
Insights
Insights
Insights
When to book
4 weeks
in advance
Our data shows that travelers who book at least 4 weeks in advance save around 20% compared to booking last minute.
Insights
Insights
Insights
Insights
When to travel
March
Cheapest • 14% price drop
June
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
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KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to Portland!
Flight Deals
Booking Insights
Expert advice
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

Tue, Apr 21 - Wed, Apr 29
Delta Logo
6:21 pm - 12:46 am
ORD
-
PWM
5h 25m
1 stop
Delta Logo
5:26 pm - 10:15 pm
PWM
-
ORD
5h 49m
1 stop
$197Delta
Tue, Apr 21 - Wed, Apr 29
Delta Logo
5:04 pm - 12:46 am
ORD
-
PWM
6h 42m
2 stops
Delta Logo
5:26 pm - 10:15 pm
PWM
-
ORD
5h 49m
1 stop
$202Delta
Tue, Apr 21 - Wed, Apr 29
Delta Logo
12:52 pm - 12:46 am
MDW
-
PWM
10h 54m
2 stops
Delta Logo
12:46 pm - 5:58 pm
PWM
-
MDW
6h 12m
1 stop
$202Delta
Tue, Apr 21 - Wed, Apr 29
Delta Logo
5:04 pm - 12:46 am
ORD
-
PWM
6h 42m
2 stops
Delta Logo
6:30 am - 4:42 pm
PWM
-
ORD
11h 12m
2 stops
$208Delta
Fri, Apr 10 - Mon, Apr 13
United Airlines Logo
6:10 pm - 9:40 pm
ORD
-
PWM
2h 30mnonstop
United Airlines Logo
6:04 am - 8:00 am
PWM
-
ORD
2h 56mnonstop
$209United Airlines
Tue, Apr 21 - Sat, Apr 25
United Airlines Logo
6:10 pm - 9:40 pm
ORD
-
PWM
2h 30mnonstop
United Airlines Logo
7:33 pm - 11:43 pm
PWM
-
ORD
5h 10m
1 stop
$219United Airlines
Fri, May 8 - Sun, May 10
American Airlines Logo
7:44 pm - 11:22 pm
ORD
-
PWM
2h 38mnonstop
American Airlines Logo
6:01 pm - 8:14 pm
PWM
-
ORD
3h 13mnonstop
$229American Airlines
Fri, Apr 17 - Fri, May 1
Southwest Logo
7:30 am - 2:10 pm
MDW
-
PWM
5h 40m
1 stop
Southwest Logo
4:50 pm - 10:20 pm
PWM
-
MDW
6h 30m
1 stop
$229Southwest
Sat, Mar 28 - Tue, Mar 31
American Airlines Logo
8:02 pm - 11:34 pm
ORD
-
PWM
2h 32mnonstop
American Airlines Logo
12:44 pm - 6:04 pm
PWM
-
ORD
6h 20m
1 stop
$230American Airlines
Fri, Apr 17 - Fri, May 1
Southwest Logo
3:50 pm - 11:25 pm
MDW
-
PWM
6h 35m
2 stops
Southwest Logo
2:50 pm - 8:45 pm
PWM
-
MDW
6h 55m
2 stops
$239Southwest
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 $229 on the route between Chicago O'Hare Intl Airport (ORD) and Portland (PWM). Over the past month, this route was, on average, 30% cheaper than other Chicago-Portland routes. It 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 Thursday. 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 March, where tickets cost $311 (return) on average. On the other hand, the most expensive months are December and November, where the average cost of round-trip tickets is $404 and $397 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 2 stops layover the cheapest option at $275 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 20% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 18 weeks before departure.

Expert advice

Expert advice for your flight from Chicago to Portland

 
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 Frontier and 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.

Blane Bachelor

Blane Bachelor

Expert on Southwest

Blane Bachelor is a journalist and editor specializing in travel and aviation who writes regularly for top global outlets. Born and raised in Florida, Blane has worked and lived in four countries, including the Netherlands, where she’s currently based with her family. Her favorite way to get to know a new destination is by running or riding a bike around town – or hearing a spooky ghost story about local history. She will always choose the window seat.

Good to know

Low seasonJanuary
Cheapest flight$115
Best time to beat the crowds but there is an average 3% increase in price.
Most popular time to fly with an average 2% increase in price.
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 $105 for a one-way ticket and $197 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 Midway Airport to Portland flight route.

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

    American Airlines, and JetBlue 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?

    SkyTeam, oneworld, and Star Alliance are the airline alliances operating flights between Chicago and Portland, with SkyTeam 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 $377 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 $272 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 $178 or less one-way and $279 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, 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

Portland to Chicago

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 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 4306 reviews
8.1Boarding
8.6Crew
8.0Comfort
7.0Food
7.5Entertainment
Airline reviews

The last 3 flights between BWI and BDL canceled the beverage service mid- way. Just say up front that the fight is too short. Thanks!

6.0 GoodAnonymous, Feb 2026
BDL - BWI
Read more Southwest reviews

The last 3 flights between BWI and BDL canceled the beverage service mid- way. Just say up front that the fight is too short. Thanks!

It was canceled. Supposedly weather. But there was no snow in Baltimore. At least we found out before driving to airport

I have not flown Southwest in awhile and had a very pleasant experience. From ticketing to boarding to the flight. The flight left on time and landed ahead of schedule. It won't be so long next time!!

The Southwest experience has definitely taken a dive from its early days. You can no longer deferentiate from other airlines. Air travel is too expensive. Southwest is no longer budget friendly. They have lost me as a loyal customer.

Flight was hours late, unable to sit next to spouse, I have had so much better experiences. Substantially better, only saving grace was that it was a short flight.

An entire day of delays. Cost lots of money. Meals and a hotel.

The WiFi and crew on the plane were good, however, the boarding experience was awful. I paid for the Choice Preferred and was boarded in group 5 so all overhead storage was full. They found room for our luggage, but further back making getting off the plane a nightmare. Also, we were in row 6 and the seats were extremely uncomfortable. Both my daughter and I had no leg room and couldn’t wait to get off the plane.

The charges were ridiculous for an hour flight and the turbulence was very scary.

Still need to work out the kinks on the new assigned seating boarding process. Otherwise, a very good flight.

WiFi did not work. Boarding with the new seating assignments took too long. The temperature in the terminal was obnoxious. +/- 80°

I was happy that I was able to get a last minute flight but unfortunately my seat was a middle seat. Even with Delta Comfort I wasn't comfortable

There’s not much to say about a one hour flight. This is a connection from LA to RNO that I missed the previous night due to a mechanical check delay on my originating flight from JFK to LAX. The short flight itself was fine. Instructions from the pilot and crew were per usual. The coffee was barely lukewarm, which possibly was purposeful so we would down it quickly. Bags were already on carousel upon reaching baggage claim, which was excellent.

Flight was warm for first few hours and quite rough

Seat was extremely hard which made even a short 1 hour 20 minute flight fairly uncomfortable.

Everything was good except wifi and a leaking drink chiller. The floor was all wet and my bag was soaked. Did not notice until debarking. Have not heard back from Delta. Even though this was leg one of an international flight in first class, they denied access to their Sky Club - very disappointing!

The staff was fine. The plane was extremely tight, and I paid for the wifi and it did not work at all. I was actually going to ask for a refund.

two hour delay and the Delta representative on the PA system was unable to understand

An awesome flight crew. FC seat cushion just doesn’t cut it for a 3+ hour flight.

2+hrs delay without any reason provided and a cramped flight

We waited an hour on the runway to get a gate in Orlando

This trip did not start off well. The inbound flight was delayed about 20 minutes. Then, after initial onboarding, the passengers had to deplane due to a mechanical problem. That took about 30 minutes to fix and be cleared. Then, reboarding was chaotic. It took a long time to sort passengers and two passengers on standby were ticketed but there was no seat. So, they had to deplane. One of the flight crew was trying to help passengers figure out a place to put their carry-on bags and that took more time. In the end, our scheduled 10:30 am departure did not actually take off until about 12:05 pm CST. The flight itself was long but we got to Houston. Some passengers missed their connecting flights and had to rebook. Not the best of flights I've had.

We were delayed for about an hour from taking off due to traffic control procedures at the destination airport. But once in the air, the flight went well. The crew members were great and provided cabin service despite moderate turbulence during much of the flight.

Short flight, but no drink/snack service. The flights both going and coming were delayed.

Not being stranded in Chicago for her airport to 11:30 tomorrow morning the 3rd

I was fully checked in the prior night and i was unchecked and then didn’t have a seat when I boarded. Instead of an aisle seat, I was out in the middle seat of the very last row of the plane.

In overall it was a good experience, the only down point was that the entertainment screen was working properly.

They lost my luggage, so, not happy. The crew was nice but my suitcases never made it, still trying to find out what happened!

I understand weather is an issue, but making us chase our plane down at five scheduled gates across three terminals in an airport the size of O'Hare was unfair. They'd have probably been better off to leave gates as TBD until the inbound plane is in final approach instead of running us all over the place. Also, props to the consistently-unprepared ground crew in Richmond for once again leaving my lane parked short of the gate because they couldn't have a crew in place on time with 2 hours notice...

cabin crew was OK, food was OK, the trip from the US to Munich was actually pretty bad comfort wise. Noisy aircraft, lights never dimmed even in Business class (night flight) barely sufficient amenities for the price. I have millions of miles with United but TBH American is gaining ground and Delta has always been marginally better then United although on paper United has more longes and cheaper upgrades.

Essy to get on. The hostess gave very little pop, the plane was late getting in, and we are still waiting for our bags. This sucks. :/

We were made to wait in the airport for six hours for a flight that was ultimately canceled.

Both flights were significantly delayed. The flight experience itself was great.

My flight got delayed and eventually canceled, then rescheduled. I and several others had a connection from Boston to Paris and asked several times if we would make it. They assured us we would and then rebooked us mid flight without our consent and closed doors early even though they said they communicated we were a bit delayed. We got stranded in Boston and I opted with being rebooked for a different connection to France since they refused to pay for a Hotel. I've now been in Europe for 5 days and still haven't recieved my bags. There was absolutely no urgency for the fact that I'm in a foreign country with absolutely no change of clothes or any of my medication. Such an overwhelming and frustrating experience.

Automated scanning was slow and somewhat haphazard. Too many people were unfamiliar with the tech and were forced to learn on the fly. The hands off approach of the gate staff made it more uncomfortable. This needs work. Overall the flight and cabin crew were excellent.

The crew for the flight was A+ top notch. They were friendly and professional and made the flight a very relaxing and enjoable.

Rude crew member. She seemed annoyed at me without me saying a single word. Also loudly admonished me for having my bag next to my seat instead of tucked away before landing. Just telling me to put it away and guiding me without giving me a lecture would have been enough.

No included food for a 5 hour flight and the entertainment was only accessible if you had wired headphones (not provided). Otherwise though, great and smooth flying and customer service.

Crew were fantastic and so catering and wonderful! Full score for the entire crew!

Because of weather and mechanical issues our flight was 4 hours late. The only compensation offered to us was a meal voucher to be used only at Boston Airport and only on the day issued. But by the time it was offered to us all the restaurants were closed, so there was no way to use that offer.

Friendly crew, efficient boarding and flight arrived early. Couldn’t ask for a better experience

It was an older plane. First Class was not especially roomy or comfortable. It was a short flight so there were no meal but they did offer mixed nuts which used to be normal but now is rare. Crew member was very polite and professional.

Flight to Tampa was delayed taking off due to plane arriving late but no other issues

As previously stated the delay I experienced flying from Wichita to Chicago caused a host of issues. When I finally was able to be booked on the last remaining American flight from Chicago to Cincinnati, the gate changed four times with the last change occurring very near the scheduled boarding time. While I didn't have a problem moving from gate to gate, I did notice and make note of others that had mobility issues and had to move each time for the gate change.

Maintenance took a very long time and then we were in a holding pattern. While a one-off maintenance issue is standard, there were delays on both of my flights for this trip based on maintenance issues with the planes, which delayed both flights over 45 minutes. Thankfully, I didn't have any connections but it wasn't an experience that would make me pick AA if I have other options.

No Snacks or Entertainment. The flight was short, snacks should still be given.

See prior comment about how Kayak mishandled my reservation and delayed my arrival by 6 hours.

Boarding delayed 20 minutes for no reason, no wifi, in flight entertainment, or snacks / waters?

Delayed an hour due to operational issues. Minimal apologies or care for the significant inconvenience caused. Landed at nearly 1am and they still couldn’t find ground staff to get us off the plane promptly.

The aircraft had several problems - from excess fuel to non operational ac. Two hours of delay in Chicago could have been avoided with proper planning and aircraft maintenance.

Crew in Columbia was not prepared for landing. It was a bit of a disaster and getting bags took forever.

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

Information on your arrival and departure airports