$221 Find Cheap Flights from Chicago to Alaska - Compare and Save

I paid extra to choose a seat. When arriving at the gate after a very stressful check in at the airport, realized did not get the chosen seat that I PAID for. When I called the airline I was told I did not pay to choose a seat and could not be refunded, but I DID pay extra to choose a seat. And of course, got stuck in a MIDDLE seat. Since the seats are now crammed together, this is especially uncomfortable. The check in for baggage was ridiculous, it was a mile long and the kiosk to check in for the flight was very confusing. We finally sought out help and a very rude representative quickly went through the kiosk and printed a boarding pass that did not provide the PAID for chosen seat. Didn't get to get on the return flight because the flight coming in was delayed several hours, missed the flight by 3 minutes!!!!!!! You really can't hold the door for 3 minutes for a passenger you KNOW you are waiting for??? What stress and had to wait 4 MORE HOURS to get a flight home because you could not keep the door open 3 minutes. 3 minutes. Had only 20 minutes to get from flight to connecting flight and was accused of taking too long to get from gate to gate in Chicago. Flights were delayed all day long coming in and going out, you would think you could wait 3 minutes to allow passengers to get to the connecting flights. HUGE inconvenience, stressful and makes for a really LONG day when the flight leaving Des Moines to Chicago was horribly delayed, already had a horrible experience and missed the connecting flight by 3 minutes. 3 minutes. Airplane was still there, the door closed, why on earth is it such a huge deal to wait a few minutes when flights were already delayed ALL DAY LONG and why is it such a huge deal to REOPEN the door to let another passenger on??!! I used to like Alaska Airlines. I just plain hate flying in general now. The airlines have 0 (zero)care about the people buying tickets and making travel plans and how stressful flying is now. Zero care.

They overbooked the flight! Or they said it was over weight, very unnerving as flying is a gamble anyway. They were waiting for six passengers to give up their seats, before they would board the flight, they were offering $1100. I’m guessing towards the purchase of the next ticket which I would never purposely fly with American Airlines. It was just the only flight available with what I needed. American Airlines is the top two worst airlines to fly with. And then after waiting an hour and four minute delay departing they ended up seating the people that they had asked to give up their seats anyway turns out they were not overweight after all. So all of that in a delayed flight and a delayed landing in Des Moines for nothing American Airlines is in competition with United Airlines for the worst airline to fly with.

The seat was comfortable, but I paid for upgraded seats and they did not state that there was no outlets for devices.

Extremely professional crew there are very friendly and first class. Everything worked well on the plane. Food was to be expected. Drinks were very good. Shout out to Charlie in first class who was an excellent flight attendant.

Thanks for all you do to keep us safe and on time!

I like flying Alaska Airlines. I think the staff are happy, the plane is comfortable, the entertainment reasonable, the food acceptable.

I had a great trip. Everything was on time, easy boarding and kind attendants.

Good legroom, good food. Great landing, comfortable seat, good communication from pilot and crew. I wasn't thrilled that we were an hour late but it happens. The only two minor things was that the garbage pickup was slow and your windows need washing. Overall we will beback

In order to watch a movie you have to buy wifi access

Very close to on-time takeoff and landing. Attendants were all great - Julia was best! Joined the Alaska Air Rewards and will fly with them again!

I'm 6' 2" and even in economy plenty of leg room

Horrible experience. Delta delayed the flight to 11pm which happens. Apparently the pilots were there but we were waiting for flight attendants to arrive from Detroit and they were delayed. They could have made arrangements but that’s fine. What was truly horrible was that at 10:50pm the pilot comes out and says the flight will be cancelled but hasn’t been cancelled yet in the system. It’s being cancelled because the pilots have timed out. As soon as that plane got delayed past 10:50pm delta knew it couldn’t fly. Yet they made us wait around for hours. When the flight finally got cancelled all the area hotels were booked and flights for the next day were unavailable until midday. All I wanted was to spend one day with my family before needing to fly abroad on another delta flight. That will be my last flight with them. I’ll take my 800k miles flown and annual spend to an airline that isn’t so thoughtless.

THI IS THE 3RD CONSECUTIVE FLIGHT FROM ORD TO MSP THAT HAS BEEN DELAYED 2+ HOURS. CRAZY

The plane was a rather tired 737-800, with old style small luggage bins. Poor air flow. USB charger in the infotainment system was not functioning. The flight was 2 hours late due to crew rest requirements (not their fault). On arrival in Seattle, waited on the tarmac for 30 minutes with very few updates from the crew.

The crew was very inconsiderate and rude. My flight was scheduled to depart at 6:00am. I received a call from the crew at 5:40am, asking if I was going to make the flight because I was the only one that hasn't boarded yet and boarding ends at 5:50am. I let them know that I will be at the gate in a few minutes, before the 5:50am cutoff. When I arrived at the gate at 5:45am the gate was closed. Departing early on last minute notice without having all passengers on board is inconsiderate and unprofessional.

Very easy to use and convenient, you can perform any action within the same portal

Okay considering we had weather delays which the Pilot notified us of immediately!

The boarding was organized and informative but the plane was tight meaning that you were sitting on one another and extremely uncomfortable. It’s disappointing that can’t have common seating comfort on the plane.

Everything could have benn better. Short fly, no food, no entertainment and no wifi.

Stop changing gates. Stop cancelling flights Stop moving my seat.

Price was crazy watch it if you Chan he your flight

On time, easy boarding. Anytime you sit in an economy seat, it’s uncomfortable. New plane and the bathrooms were in the galley at the back of the plane which seemed odd.

Terrible service - they don’t want to be there and bad food. Entertainment system in economy from the 2000s

No drink service but there was no N/A as an option to choose. Seats were extremely tight. I am under 5.5 and I bumped my knees have no idea how taller people could manage.

Flight delayed, last seat on the plane, no arrival Gate available due to the plane departing late

Kayak booked this flight with only 1h 20min layover in Chicago. This made it impossible for me and several other passengers to reach this flight. Moreover, the gate closed boarding in spite of several passengers still on their way without waiting even one more minute. However, the plane departed with 20min (!) delay, i.e., there would have been at least 15 min time to let the delayed passengers board without causing any delays. I complained and as a "thank you" the attendent booked us on the last (!) flight to Indianapolis ~7h later! Thankfully, I caught the spitefulness and the United customer line rebooked the flight to an earlier flight. Although I can't grade this particular flight since I never had a chance to take it, Kayak made the mistake of a too short layover and the crew at the gate was awful.

Flight did not have wifi service. It was experiencing technical difficulties. Definitely and old plane that needs updating.

Old 757 with poor entertainment system. United no longer partners with United for free text and email. O'Hara an absolute disaster! Limited gates clauses two hour delay. Unfortunately this appears to be the norm.

It was a good experience, unfortunately my checked baggages were come late and not arrived on time.

Great experience. Boarding was fast, staff were very nice and funny, everything at the seat worked well.

First class snacks - stewardess gave out multiples to everyone until there was almost no selection left when she got back to me last in first class cabin. Nothing left that I would eat.

My feedback from the trip to Columbia to Chicago was meant for Chicago to Denver.

The WiFi was out gr entire flight. Had to Diane for almost 1 hour to wait for a gate to open up for plane to dock. Very bad experience.

DELAYED AGAIN and AGAIN and AGAIN - not only that, you delay in 20 minute increments for hours and hours instead of having an accurate delay understanding.

AA was fine....the overall experience was subpar, but not due to the airline due to broader issues

No ground air conditioner for the plane. Very hot and humid prior to take off which was an uncomfortable period of time.

Check-in process was poor, very poor, only one person to check-in all passengers, so if one passenger had a check-in issue, all other passengers were delayed. All check-ins should have two airline staff to check-in passengers.

The flight up was great no issues. The flight back home was a cluster. I was told the plane I was waiting on was giving to another flight which caused me to miss my connection flight. Granted the airline did great with getting hotel and vouchr for food.

Flight was delayed and so much of inconvenience related to the gate change.

Nothing was good about this flight. Although the flight actually departed more than 3 hours late, due to “air traffic control management” we pushed back from gate 2 hours and 20 minutes late and proceeded to sit 100 yards from gate for and then n tarmac for another 1/2 hour additional 20 minutes