PDX - CHI

$139 Find Cheap Flights from Portland to Chicago

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 Chicago departing on 5/24. 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

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Portland to Chicago.
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Portland to Chicago.
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Everything you should know

Cheapest round-trip
$280
Typical prices: $427-$285
Frontier
Sun 5/24Sat 5/30
PDX - ORD • 1 stop
Cheapest non-stop
$286
Typical prices: $419-$276
Alaska Airlines
Tue 6/23Sat 6/27
PDX - ORD • Non-stop
Advice from real travelers
AI-powered summary based on content written by travel experts. AI can make mistakes.
Southwest's two free checked bags suit luggage needs.
The CTA Blue Line from O'Hare is a reliable 45-minute trip.
Expert advice
Expert advice
Expert advice
Expert advice
Top airlines
Cheapest • from $280 (round-trip)
Best reviews • 8.0 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Nonstop flights
You can fly direct with Alaska Airlines, American Airlines and others. Average duration is 4h 08m
Direct flights
Direct flights
+1
+1
Direct flights
Direct flights
+1
Top routes
Cheapest
Most popular
Insights
Insights
Insights
Insights
Top layover airports
Cheapest • Avg $211 (round-trip)
Shortest trip • 5h 51m (one-way)
Insights
Insights
Insights
Insights
When to book
in advance
Our data shows that travelers who book at least 4 weeks in advance save around 52% compared to booking last minute.
Insights
Insights
Insights
Insights
When to travel
Cheapest • 69% price drop
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
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Flight Deals
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Expert advice
Flight Deals

Cheap Flights from Portland to Chicago (PDX-CHI)

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

Sun, May 24 - Sat, May 30
Frontier Logo
5:31 pm - 6:34 am
PDX
-
ORD
11h 03m
1 stop
Frontier Logo
8:46 pm - 11:50 am
ORD
-
PDX
17h 04m
1 stop
$280Frontier
Sun, May 24 - Sat, May 30
Frontier Logo
5:31 pm - 6:34 am
PDX
-
ORD
11h 03m
1 stop
Frontier Logo
8:46 pm - 11:50 am
ORD
-
PDX
17h 04m
1 stop
$281Frontier
Tue, May 26 - Sat, May 30
Frontier Logo
5:46 pm - 8:32 pm
PDX
-
ORD
24h 46m
1 stop
Frontier Logo
8:46 pm - 11:50 am
ORD
-
PDX
17h 04m
1 stop
$282Frontier
Sun, May 24 - Sat, May 30
Multiple Airlines Logo
7:00 am - 1:22 pm
PDX
-
ORD
4h 22mnonstop
Multiple Airlines Logo
8:46 pm - 11:50 am
ORD
-
PDX
17h 04m
1 stop
$283Multiple Airlines
Sun, May 24 - Sat, May 30
Multiple Airlines Logo
7:00 am - 1:22 pm
PDX
-
ORD
4h 22mnonstop
Multiple Airlines Logo
8:46 pm - 11:50 am
ORD
-
PDX
17h 04m
1 stop
$284Multiple Airlines
Sat, May 30 - Wed, Jun 3
Frontier Logo
5:31 pm - 6:34 am
PDX
-
ORD
11h 03m
1 stop
Frontier Logo
9:37 pm - 11:50 am
ORD
-
PDX
40h 13m
2 stops
$285Frontier
Sun, May 24 - Sat, May 30
Southwest Logo
11:55 pm - 5:50 am
PDX
-
MDW
3h 55mnonstop
Southwest Logo
6:05 pm - 8:25 pm
MDW
-
PDX
4h 20mnonstop
$305Southwest
Tue, May 26 - Tue, Jun 2
Southwest Logo
11:55 pm - 5:50 am
PDX
-
MDW
3h 55mnonstop
Southwest Logo
6:05 pm - 11:10 pm
MDW
-
PDX
7h 05m
1 stop
$315Southwest
Tue, May 26 - Wed, Jun 3
Delta Logo
11:12 pm - 8:43 am
PDX
-
MDW
7h 31m
1 stop
Delta Logo
12:53 pm - 9:46 pm
MDW
-
PDX
10h 53m
1 stop
$325Delta
Sun, May 24 - Sat, May 30
Allegiant Air Logo
7:17 pm - 8:23 pm
PDX
-
RFD
23h 06m
1 stop
Allegiant Air Logo
1:01 pm - 6:27 pm
RFD
-
PDX
31h 26m
1 stop
$421Allegiant Air
Booking Insights

KAYAK's insights & trends for Portland to Chicago flights

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

How much is a round-trip flight from Portland to Chicago?

This analysis is based on the cheapest round-trip price found on KAYAK in the last 12 months by searching for a flight from Portland to Chicago departing in May.

What is the cheapest Portland to Chicago flight route?

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

The cheapest return flight from Portland to Chicago costs $289 on the route between Portland (PDX) and Chicago O'Hare Intl Airport (ORD). It is also the most popular route.

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

The average price of all round-trip flights from Portland to Chicago clicked on KAYAK for each day over the last 12 months.

If your flying dates are flexible, you should consider flying to Chicago on a Wednesday, as we generally find the cheapest rates on that day for this route. On the other hand, Monday is the most expensive day to fly from Portland to Chicago. For your return ticket, we recommend flying on a Tuesday and avoiding Sundays for the best deals.

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

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Portland to Chicago, 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 is November, where tickets cost $103 (return) on average. On the other hand, the most expensive months are August and September, where the average cost of round-trip tickets is $800 and $760 respectively.

Can I save money by flying with a layover from Portland to Chicago?

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 $363 on average.

How far in advance should I book a flight from Portland to Chicago?

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, 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, you should book around 4 weeks before departure, which saves you about 52% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 15 weeks before departure.

Expert advice

Expert advice for your flight from Portland to Chicago

 
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, ORD and MDW

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 and Alaska 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.

Gabriel Leigh

Gabriel Leigh

Expert on PDX

Gabriel is a writer and video creator. As senior content producer for Flightradar24 and Monocle’s transport correspondent, he keeps a close eye on aviation in particular. He has also written travel articles for the likes of The New York Times. Born in New York but raised around the world, he now lives in Sweden. He’s been to 75 countries, flying 2.3 million miles on 113 airlines and through 234 airports in the process.

Good to know

Low seasonJanuary
Cheapest flight$140
Best time to beat the crowds with an average 29% drop in price.
Most popular time to fly with an average 4% increase in price.
Flight from Portland to Chicago O'Hare Airport

When to book flights from Portland to Chicago

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

  • Where can I park my car at PDX long-term before my flight to Chicago?

    Near the tunnels that connect the north and south terminals, PDX has long-term parking lots. Further away, PDX has an economy lot. This economy lot is less expensive and there is a 24h shuttle service for free that will take you to your terminal.

  • Is there a USO lounge for US military at PDX?

    The USO lounge at PDX is before security on the mezzanine level. It is open Monday to Friday 9 am to 5 pm. The USO is closed on Saturday and Sunday. This lounge is available to active-duty military service members and their families. Local and transportation information is available here. Amenities at the lounge include TV, Xbox 30, Wi-Fi, computers, laptops, toiletries, free drinks, and lounge seating.

  • What are the major airports in Chicago?

    The two major airports in Chicago are Chicago O'Hare International Airport (ORD) and Midway International Airport (MDW). ORD is a hub for United Airlines and American Airlines and the airport has four terminals. Midway, a hub for Southwest Airlines, is much smaller, with just one terminal and three concourses.

  • How can I fly from PDX to the Chicago airports?

    United Airlines and Alaska Airlines operate non-stop flights from PDX into Chicago. All of these flights tend to land at ORD airport. Southwest operates non-stop flights from PDX that land at MDW. Alaska Airlines, Delta, Spirit, and United Airlines operate one stop flights from PDX to ORD. Some layover cities include Las Vegas (LAS), Seattle (SEA) and Denver (DEN). Delta operates one stop flights from PDX that land in MDW. These flights tend to stop at cities such as Atlanta (ATL) and Detroit (DTW).

  • What is the cheapest flight from Portland to Chicago?

    In the last 3 days, the lowest price for a flight from Portland to Chicago was $140 for a one-way ticket and $280 for a round-trip.

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

    Even though you are not required to have a passport, keep in mind that an official ID is needed to board the airplane.

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

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

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

    The Boeing 737-800 is the aircraft model that flies most regularly on the Portland to Chicago flight route.

  • Which airline alliances offer flights from Portland to Chicago?

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

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

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

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

    The two airlines most popular with KAYAK users for flights from Portland to Chicago are Southwest and Alaska Airlines. With an average price for the route of $294 and an overall rating of 8.0, Southwest is the most popular choice. Alaska Airlines is also a great choice for the route, with an average price of $340 and an overall rating of 7.9.

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

    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.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago 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?

    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 with an airline and back to Portland with another airline.

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

    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 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

  • Looking for a cheap flight? 25% of our users found flights on this route for $212 or less one-way and $395 or less round-trip.
  • Portland International Airport (PDX) has designated areas where children can play as they wait for their plane. This area is also very convenient for parents to relax. One of these kid-play areas is at gate C-17. The other is before security at terminals D/E.
  • Both major airports in Chicago provide private spaces for nursing mothers. Chicago O'Hare International Airport (ORD) provides Mothers Rooms for nursing mothers to breastfeed or pump. These private, sanitized spaces are located in terminals 1, 2, 3, 5, and in the Multi-Modal Facility. ORD also provides lactation pods, free standing privacy units for nursing mothers, in terminals 1, 2, and 3. Midway International Airport (MDW) provides a Mothers Room on Concourse C, next to the yoga room. MDW also provides a free-standing lactation pod on Concourse A at gate A5.
  • PDX has partnered with DoveLewis to make therapy dogs available throughout the airport in order to comfort confused, bereaved, or anxious travelers. Retired Guide Dogs for the Blind wear gray DoveLewis vests and passengers are encouraged to smooch, hug, pet, and cuddle these dogs. The dog handlers are trained to spot people in emotional need of assistance in stressful situations.
  • The Hollywood Theater on Concourse C of PDX shows short films that are 10min or shorter, made by Oregon filmmakers. If you have some time before your flight, consider stopping into this 22-seat theater. It is open 24h a day, and it is free.
  • If you want to stay near the airport the night before your flight to Chicago, PDX has many comfortable hotels nearby that offer free airport shuttles to your terminal. Some examples of these hotels are the Red Lion Hotel Portland Airport, The Howard Johnson By Wyndham Portland Airport, and The Ramada By Wyndham Portland Airport.

Prefer to fly direct from Portland to Chicago?

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

Direct departures

Portland to Chicago

Monday

Alaska Airlines,American Airlines,Southwest, +1 more

Alaska Airlines,American Airlines, +2 more

Tuesday

Alaska Airlines,American Airlines,Southwest, +1 more

Alaska Airlines,American Airlines, +2 more

Wednesday

Alaska Airlines,American Airlines,Southwest, +1 more

Alaska Airlines,American Airlines, +2 more

Thursday

Alaska Airlines,American Airlines,Southwest, +1 more

Alaska Airlines,American Airlines, +2 more

Friday

Alaska Airlines,American Airlines,Southwest, +1 more

Alaska Airlines,American Airlines, +2 more

Saturday

Alaska Airlines,American Airlines,Southwest, +1 more

Alaska Airlines,American Airlines, +2 more

Sunday

Alaska Airlines,American Airlines,Southwest, +1 more

Alaska Airlines,American Airlines, +2 more

See more direct flights

Direct returns

Chicago to Portland

Monday

Alaska Airlines,American Airlines,Southwest, +1 more

Alaska Airlines,American Airlines, +2 more

Tuesday

Alaska Airlines,American Airlines,Southwest, +1 more

Alaska Airlines,American Airlines, +2 more

Wednesday

Alaska Airlines,American Airlines,Southwest, +1 more

Alaska Airlines,American Airlines, +2 more

Thursday

Alaska Airlines,American Airlines,Southwest, +1 more

Alaska Airlines,American Airlines, +2 more

Friday

Alaska Airlines,American Airlines,Southwest, +1 more

Alaska Airlines,American Airlines, +2 more

Saturday

Alaska Airlines,American Airlines,Southwest, +1 more

Alaska Airlines,American Airlines, +2 more

Sunday

Alaska Airlines,American Airlines,Southwest, +1 more

Alaska Airlines,American Airlines, +2 more

See more direct flights

Reviews of the top 5 airlines serving from Portland to Chicago

 
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 Chicago? 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 4314 reviews
8.0Comfort
7.0Food
8.6Crew
7.5Entertainment
8.1Boarding
Airline reviews

The entire experience from boarding to landing was amazing! The crew were very friendly. Will definitely be back.

10.0 Excellentlarry, Apr 2026
LGB - PHX
Read more Southwest reviews

The entire experience from boarding to landing was amazing! The crew were very friendly. Will definitely be back.

no service at all due to turbulence. they should've at least given us snacks, there were only 10 people on the entire flight.

First time I've had to use the disabled accommodations. And I could not have had a better experience with Southwest, i was having trouble getting from one terminal to another due to my heart failure. And the next thing I know a Southwest agent had made sure. I had a wheelchair at all my flights. Can't thank them enough.

Delayed flight, lack of information, boarding process is a mess as is the carryon luggage causing issues when leaving the plane….just a poor experience.

Comfortable. Easy. No problems. Just wish they had gf options for snacks.

The crew was very kind and made going to Hawaii relaxing and fun to look forward to! Thank you Southwest for a pleasant flight!

This leg was much better, but we did have to have a 3 hour lay o er after coming from a very exhausting hiccup with our flight from BNA to Den

We waited in the airplane for over 45 min for a southwest employee to make the flight. This cause over half the plane to miss their connecting flight in Denver. When we confronted the desk upon arrival, they told us the only flight they had was the next day leaving at 8:50 pm!!! Or they offered to get us to Burbank or LA, but after that we were on our own to get back to Santa Barbara. I paid for a flight from sba to bna bna to sba. My re entry into mom mode has been 💯 rough because of southwest mistake with my flight. And now I’m leaving to Reno tomorrow for a vballl tournament and just discovered that my leg in Vegas has me and my 3 kids on a stand by flight even though I had booked these ticket last year November!! Do better southwest!

Southwest is kind of a slum airline. It’s gotten more expensive over the years for less and less service. I am a Southwest Chase Visa card holder and was forced to choose a seat in the 26th row in the middle seat. However my wife who is a rewards member but doesn’t hold a card or anything else, gets randomly assigned a normally paid seat in row 6! How does that work?

For the first time in a long time, the Wi-Fi actually worked the entire flight! The flight crew was amazing as usual.

very nice blankets and comfortable seats. great service. Great flights.

great experience just at the end, we got in early and there wasn't anyone at the gate for 30 min so we had to just sit on the tarmac

Generally Good. Outbound flight was marred by a continuously s creaming baby. Fortunately the flight was only 90 mins long it would be nice if people traveling with small childres could be centered in one part of the plane. Also, you need to adapt your servey to include a "not applicable " option for things like food and entertainment, which are not offered on shorter flights. I fily Alaska by choice as given all the cirumstances, I fel\el you do a good job.

I was seating in 26A and the children in 27A and B were kicking me non-stop. They kicked me for hours nonstop and the parents refused to get off their phones or correct them. I kindly asked multiple times and got screamed at by the mom that her son is disabled. I told her I get it, but that I matter too and she is responsible for her child. He then kicked me so hard my drink spilled. Not one crew member or other passenger said or did a thing. It was so horrible.

Birding was slow. extremely slow; please do experiments on efficient plane boarding experiences; especially regarding passengers that pass their seat number…

Pretty smooth ride!… a little tight in the back and would’ve loved to had a movie screen… couldn’t beat the price to the West Coast!

I like not much people. Could tell the kids to be quiet.

I liked everything except, I left a brand new Switch 2 on the plane and talking to anybody about it is nearly impossible. I had to fill out a form and hope they get back to me in the next 2 weeks. I really hope they contact me. I saved for that thing for over a year and my son is heart broken.

Fight attendant excellent Food very good, not great Seats were stiff and uncomfortable Flight was overall very nice. Last three flights were burdened with miserably uncomfortable seats. Hard stiff no padding.

The ground crew was very good. They communicated clearly and continued updating. The flight crew was fine. The flight crew on the March 20th flight from MCI to Portland was excellent.

Flight delayed two hours , missed connection flight then connection cancelled- horrible experience with hotel

Omg the disaster at the security was on another level! “Go to this end, sorry closed now, go to that end”. Ridiculous! This took over an hour! As far as the airline was concerned although I booked nearly a year ago I couldn’t get my bag tag - stand in another 15 minute line or my seat on Hawaiian Airlines- 5 more minutes! Then my TSA status was denied. Like what the heck! Makes a person not want to travel with this amount of incompetence

The Honolulu Hub needs 2 to 3 times the amount of things to do as well as shuttles that transport to/from gates and terminals. Arriving from OCONUS locations; transferring to CONUS locations its a miserable experience. Fetching and re-checking bags, then returning to a gate across the airport take longer than any other large airport. If youre confused by what I mean, the process goes like this: Disembark plane Walk a mile to the main terminal Walk half a mile to baggage claim Wait 40 minutes for baggage Walk a mile to re-check-in baggage Wait 20 minutes for checking in those bags Fo back through the wrong TSA line because the signage is poor Almost miss the connecting flight because your gate is across the airport.

The checking was disaster, the crew wasn't behave well. It took us two hours to check in, after that thr line at the TSA was long, we barely make the flight. Bad airline

Fabulous if you have a portable wheelchair. They can store it in the galley and you can just walk out with it. Really nice and the flat seats are just incredible, very nice. iPads for movies, also pretty nice,

The crew were exceptionally nice and accommodating. My wife was tired after the flight from Haneda, Tokyo. They let her sleep and served her dinner later after she woke up, before we landed in PDX.

No charging outlets worked. Other than collecting trash attendants didn’t come around. No one could hear flight attendants announcements during the flight. Seat pads were horrible. Sitting on a board for 5 hours. What happened to Hawaiian airlines comfort, hospitality, and extras? Our pilots did an excellent job trying to minimize turbulence and incredible job in landing in windy conditions.

I like that if they asked you to checked in a bag at the gate they give you priority to board

Horrible food and crew. Crew were laughing and talking loud while people were trying to sleep

Yall need to integrate your system with Alaska more efficiently. They booted me off the first flight because of a discrepancy on your end.

Standard flight with a drinks and a snack- overall very quick flight. The flight attendants were very strict, bordered on rude.

Delayed - weather wasn't bad at either end. Also sat on tarmac in ORD.

boarded early to only find out that flight would sit at gate for 45 min to an hour. Landed in chicago and sat on runway for over an hour before got to gate. Total delay was extensive for a 45 min flight door to door.

The flight was significantly delayed. The inbound flight from EWR was delayed departing because of mechanical problems. My original departure from CLT was 5:28 pm but due to the delay of the inbound flight, after arrival, deplaning, cleaning, boarding, we did not push back from the gate until 9:00 pm. Once in the air, the flight was smooth and what was originally supposed to be an arrival in ORD at 7:30 pm local time turned out to be 9:35 pm.

The flight I was supposed to be on was supposed to take off at 1:50 from State College. It was delayed over and over and over again until somehow I had to rebook on a flight that was supposed to have left State College at 8 am that morning but didn't end up taking off until almost 6 pm. Not only was this completely unacceptable, the "token from United" was a 15 dollar meal voucher that has to be used by today. I would personally like some miles added to my account for this inconvenience. I was in transit for 8 hours from the time I arrive at State College Aiport to when I got home. I was supposed to be home at 3 pm and I returned at 8 pm. Unacceptable. I have not been on an on Time united flight in nearly 5 years.

newer aircraft, ability to connect my headset via blue tooth for entertainment.

Very comfortable flight, snacks and drinks were good, good communication from crew. Could have used a little more information on timing of boarding for group 5

Great flight. Got to watch a movie. Smooth flight and early arrival at ORD.

It was better than excellent. The staff in Mason City were great. The young woman that pushed my wheelchair did more than could be expected of her. She came from India 17 years ago. I don't remember her name.

After arriving in Chicago, we were taxiing for 1.5 hours with infrequent and untruthful updates about the amount of time it would take to arrive at the gate. Minimally, the team could have provided timing expectations that were more truthful, especially one their original expectations were not met.

It was good, the staff was great, and the food, was as usual, tea and biscuit. Bathroom was clean, and the plane was clean as well.

Very good I can’t complain one bit. Thank you American Airlines for making my flight enjoyable and safe!

The staff and service on American Airlines were truly outstanding. I had requested wheelchair assistance for my mother due to her knee issues, and the team went above and beyond every step of the way—from boarding in Boston to our arrival in Chicago. Their care, professionalism, and attentiveness made the entire experience smooth and stress-free. I’m very grateful for the support they provided.

The new planes (American Eagle) are beautiful and especially comfortable. The flight attendants are consistently professional and courteous. And, while it may seem inconsequential, the new liquid tube of coffee creamer—in contrast to the powdered coffee creamer—makes all the difference in a cup of coffee.

I'm not sure American is capable of on-time arrivals and departures. When you land at ORD, you almost always get held on the tarmac because your gate is still occupied. I may have missed my connection, but that ended up up being significantly delayed as well. Once again, I finally got home well after midnight.

Crew at the gate was very crabby and not at all polite. The plane was very hot the entire flight. And the seat cushion was very worn out.

The staff are very, very professional. It's what flying should feel like.

Flight was delayed half hour before boarding, but when I checked flight aware the plane that would Pick us up had a delay of more than an hour. AA should let us know in advance to avoid waiting several hours in the airport

Delays with no explanation. It could have been handled better.

Jill was the flight attendant in first class she was fabulous!! Best flight attendant I have had in years.!! And I fly every other week. Other can learn from her!!

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

Information on your arrival and departure airports

Compare transportation modes for Portland to Chicago

Transportation modeAverage priceAverage duration
Flights$7833h 55m
Trains$52446h 00m