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 |
---|---|
High season | July |
Cheapest flight | $79 |
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
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 🤙
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.
Canceled flight. No communication of this prior. Rescheduled to next day. Our good seats we purchased months ago turned into last row middle. No apology, reason, nor compensation for time and $ spent.
Friendly staff, everything went smoothly. Gluten free snacks would would be the cherry on top!
There was no entertainment - perhaps they need to upgrade the planes that service a route that is more that 2 hours long? Otherwise, everything was perfect.
The most comfortable plane ride I’ve had in quite a while.
Wonderful staff who honored sleepy overnight travelers and still met needs quietly and quickly!
The setting on the loudspeaker was painful and the crew member who did the talking spoke very quickly and repetitively, with extra little jokes that were distracting and mostly unfunny. I doubt that the main messages penetrated the noise.
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.
Very smooth checking in our luggage with a super pleasant SW agent. I enjoyed a fun entertaining movie.
WiFi did not work. For as outrageous as these flights cost, when they’re advertised with certain services/ features they should be in working order
Worst experience I had on Southwest. Still better than most, but the seating was barely tolerable.
The Southwest employees (all two of them) were very nice and cheerful despite the fact the line to self-check a bag (simply drop it off) was hundreds of people long. Thank God I arrived early to the airport because I stood in this line for at least an hour. Once on the flight that had been delayed by an hour, we had no Wi-Fi and thus no entertainment. Finally, I hope the investor strong arm tactics against Southwest pay off in a short-term windfall to your C-Suite because the rest of you are screwed. I have been a faithful Southwest customer for 15 years due to everything you just got rid of. I'm flying to Idaho and Washington in October, both places I used to simply book with Southwest without a second thought now with Frontier (Washington) and United (Idaho) because they offer everything the "new" Southwest does but cheaper and at better times, destinations, etc. This really makes me sad...
It was okay. The plane was delayed from earlier in the day, but they kept updating the departure time, sometimes later, sometimes earlier. That was stressful. Once we finally got on and took off, it was fine. I was supposed to have a connection in Chicago to Los Angeles, and the time for so late I was rebooked to arrive in LA 3 hours late. The departure time to Chicago later became early enough to have taken my original connection and arrive earlier but that wasn't an option.
It was one and half hour late... Not sure if any other experience matters.
Delayed flight. Nicest crew member was a SW pilot flying seated next to me who kindly move to seat the final passenger. Flight extra delayed. My cup of refreshment of ginger ale was so packed with ice it was literally 2 sips.
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.
Delays took 2hours and thirty minutes making me miss my connecting flight and make me sit in the Chicago airport for 9 hours
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.
check in at security was a hassle being scanned. Spirit employees were helpful and professional.
First time on Spirit. Definitely a streamline flight but I would fly Spirit again.
The flight was 3.5 hrs delayed. I was not notified prior to arriving to the airport via spirit app. or via boarding pass that I already had loaded on my phone. The agent that i saw at the counter didn’t mention anything about the delay either. I only saw the update after logging in to my email account.
The flight and boarding process was smooth. Wifi was unavailable and I prepaid for it. Have requested a refund
Had a issue with catching flight due to airline, was unable to board flight
Spirit is a very uncomfortable travel experience. It’s cheap but you are squeezed into the seats like canned meat.
Not great. Seats uncomfortable. Crew a little rude. Amenities like wifi and drinks way too expensive.
Late departure by 1:45min. No explanation why. During boarding inconsistent policing of their baggage rules. Before takeoff and lamdimg strange obsession with window shade and armrest positions. Don't know why they care. 15 min tarmac delay on arrival, they blamed airport congestion but we were the o lh flight waiting, it was clear it was due to poor staff planning (only one ground crew to receive airplanes and multiple arrivals) Got there but was rrally lame the whole trip.
The seat belt was lengthy enough that I did not need an extender. Courteous and helpful flight attendants.
It was very bad it got delayed by 2 hours.Never going to travel with spirit airlines in future.
Transportation mode | Average price | Average duration |
---|---|---|
Flights | $497 | 4h 15m |
Trains | $501 | 46h 12m |
Not what you’re looking for? Find thousands of other hotels, flights, car rentals and package deals with KAYAK.