United's Economy Plus offers up to six inches more legroom, enhancing comfort on medium-haul flights.
United offers free messaging on most flights, with Wi-Fi available for a nominal fee.
Planning a trip from Chicago to Portland? KAYAK’s data-powered insights will help you find cheap flights. Learn the best time to fly, how early to book your ticket, and other tips to secure great prices.
Low season | January |
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High season | July |
Cheapest flight | $100 |
Direct departures
Chicago to Portland
Monday
Alaska Airlines, American Airlines, Southwest, +1 more
Alaska Airlines, American Airlines, +2 more
1
Tuesday
Alaska Airlines, American Airlines, Southwest, +1 more
Alaska Airlines, American Airlines, +2 more
1
Wednesday
Alaska Airlines, American Airlines, Southwest, +1 more
Alaska Airlines, American Airlines, +2 more
1
Thursday
Alaska Airlines, American Airlines, Southwest, +1 more
Alaska Airlines, American Airlines, +2 more
1
Friday
Alaska Airlines, American Airlines, Southwest, +1 more
Alaska Airlines, American Airlines, +2 more
1
Saturday
Alaska Airlines, American Airlines, Southwest, +1 more
Alaska Airlines, American Airlines, +2 more
1
Sunday
Alaska Airlines, American Airlines, Southwest, +1 more
Alaska Airlines, American Airlines, +2 more
1
Direct returns
Portland to Chicago
Monday
Alaska Airlines, American Airlines, Southwest, +1 more
Alaska Airlines, American Airlines, +2 more
1
Tuesday
Alaska Airlines, American Airlines, Southwest, +1 more
Alaska Airlines, American Airlines, +2 more
1
Wednesday
Alaska Airlines, American Airlines, Southwest, +1 more
Alaska Airlines, American Airlines, +2 more
1
Thursday
Alaska Airlines, American Airlines, Southwest, +1 more
Alaska Airlines, American Airlines, +2 more
1
Friday
Alaska Airlines, American Airlines, Southwest, +1 more
Alaska Airlines, American Airlines, +2 more
1
Saturday
Alaska Airlines, American Airlines, Southwest, +1 more
Alaska Airlines, American Airlines, +2 more
1
Sunday
Alaska Airlines, American Airlines, Southwest, +1 more
Alaska Airlines, American Airlines, +2 more
1
The first leg of the trip was excellent. Lovely flight attendants and comfortable plane. The second leg left a lot to be desired. The flight attendant was rude when I asked for a Diet Coke, the boarding required quite a long walk and the plane was crammed and uncomfortable.
The first leg of the trip was excellent. Lovely flight attendants and comfortable plane. The second leg left a lot to be desired. The flight attendant was rude when I asked for a Diet Coke, the boarding required quite a long walk and the plane was crammed and uncomfortable.
Planes were on time. Pilot kept everyone updated. Crew was friendly and helpful
You no longer give receipts for baggage at the counter. And it is next to impossible to get it on your webpage. Spent 20 min trying and gave up... I need receipt to submit for reimbursement and don't have time to waste on your poor webpage Disappointing .....
The flight attendants were unkempt and show no customer service skills. They avoided eye contact. There were no smiles and they were dismissive and snarky.
Complete flight rebooked and 6 hours delayed. Zero accountability from the airline or Kayak for the issues and I’m injured which is why I opted to pay more to fly than drive because it’s painful to sit or stand too long. What was supposed to be a 3ish hour travel day turned into a 9 hour excruciatingly painful experience that has left me in worse pain than when I initially started.
It was a good flight, short so there was no food or water service
Checking in very confusing compared to Hawaiian Airlines - much simpler! Front checking in at airport can improve. Hawaiian service always gives the extra mile, with a smile. Alaska can use and spread the Aloha Spirit. Mahalo nui loa Thank you 🤙
Plane was delayed getting boarded and then again delayed in take-off order. Alaska Airlines must have very little clout at JFK so they don't get priority treatment. All the delays meant we missed the last flight from Portland to Eugene. Alaska did give us hotel voucher for the night...but sent us to a downtown Portland hotel rather than to a nearby airport motel which made for a longer ride at night and then again in the morning. Just made an already long, late night even longer. Hotel was an old outdated Hilton in a slightly seedy part of town. Alaska gave us Lyft vouchers for getting to the hotel, but the return voucher for getting back to the airport in the morning didn't work.
Not a fan of a 5 hour delay. I received a text from Alaska Airlines advising I would get a $100 travel voucher via email. Several days later I still haven’t received it.
My email notifications were silenced, so I didn't get word that the departing flight had changed gates. It wasn't until I noticed that few people had gathered for the flight that I checked the airport schedule board, 20 minutes before boarding. I then told several people at the old gate of the change. If I was to receive a text I would have been notified of the change earlier, Or to hear an announcement over the airport intercom.
I wish they had movie screens in the headrests. The seats are much improved, more legroom and recently renovated. Bathroom was clean. Staff was outstanding!!
As always, the entire Southwest experience was wonderful, from online booking to flight to baggage retrieval. Very grateful.
The weather could have been better. There was a 40 minute ATC delay in SFO because of marine fog and a micro cell storm delayed landing and take-off at Nashville. The gate was changed 5 minutes from boarding from gate B3 to gate C23 at Nashville airport.
After being assaulted by a flight attendant I was then brushed off as oh well because he long braids didn’t mean to whip me in the eye. I have filed complaints and will see. But like any other issue I’ve had with kayak involved it’s been trash. Last time I’ll be using your app
AC sub par. WiFi not working correctly. Ac sucked. Seats very narrow.
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.
They we able to seat my companion and I next to each other. Plane’s temperature was very cool. Willl be more prepared on return trip.
All was good and they were able to seat my travel companion next to me. Thank you.
Like the ample leg room. May as well not bother with snacks if it's only a two ounce bag of pretzels. Didn't use the entertainment option. Was there one?
What an amazing flight. I haven’t experienced this level of service in a flight in years. This will be the only way to fly to Hawaii for me in the future.
Kayak sold me a ticket after check in time. Could not check in. Could not get on flight.
Love you guys are so friendly and kind and wonderful
Agents talk too fast over intercom. I know it’s memorized and we’ve all heard it before. Just slow down a little. Stop charging for checked bags. I was pleased to get my bags promptly at each end of my flight.
Everything was great except having to check in at Alaska. That was a surprise and took extra time and effort. Should have been explained somewhere maybe on the HA electronic ticket.
It was clean and the crew was great. I wish the chairs could recline just a little more and you would provide small pillows for people with bad backs. My back is fused and a little support would be great.
I accidentally made this purchase and they wouldn’t refund me even though I called immediately to cancel it.
Once we got in the air the pilot made up some of the time of the delay. So that was really nice.
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.
Because of rescheduling, they had to put me on a flight that didn't go through Dallas
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.
Transportation mode | Average price | Average duration |
---|---|---|
Flights | $464 | 4h 19m |
Trains | $552 | 46h 12m |
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