$261 Find Cheap Flights from Alaska to Illinois - Compare and Save

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Low season

January

Cheapest flight

$261
Best time to beat the crowds with an average 10% drop in price.
Most popular time to fly with an average 1% increase in price.
Flight from Anchorage to Chicago

FAQs for booking flights from Alaska to Illinois

  • How does KAYAK find such low prices on flights from Alaska to Illinois?

    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 Alaska to Illinois.

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

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

    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 from Alaska to Illinois with an airline and back with another airline.

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

    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 from Alaska to Illinois up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

  • How many airports are there in Illinois?

    There are 12 airports in Illinois. The busiest airport is Chicago O'Hare Airport (ORD), with 92% of all flights arriving there.

  • Which is the cheapest airport to fly into in Illinois?

    Prices will differ depending on the departure airport, but generally, the cheapest airport to fly to in Illinois is Chicago O'Hare Intl Airport (ORD), with an average flight price of $386.

  • What is the cheapest day to fly to Illinois?

    Based on KAYAK data, the cheapest day to fly to Illinois is Thursday where round-trip tickets can be as cheap as $663. On the other hand, the most expensive day to fly is Saturday, where round-trip prices are $912 on average.

  • What is the cheapest time of day to fly to Illinois?

    The cheapest time of day to fly to Illinois is generally at night, when round-trip flights cost $718 on average. The most expensive time of day to fly to Illinois is generally at night, which is peak travel time and where the average cost of a ticket is $718.

  • What is the cheapest flight to Illinois?

    The cheapest ticket to Illinois from Alaska found in the last 5 days was to Chicago O'Hare Intl Airport, at $532 round-trip. The most popular route is Anchorage (ANC) to Chicago O'Hare Intl Airport (ORD) and the cheapest round-trip airline ticket found on this route in the last 5 days was $532.

  • What is the cheapest month to fly from Alaska to Illinois?

    The cheapest month for flights from Alaska to Illinois is May, when tickets cost $219 (return) on average. On the other hand, the most expensive months are January and November, when the average cost of round-trip tickets is $424 and $374 respectively.

  • How far in advance should I book a flight from Alaska to Illinois?

    To get a below average price on the flight from Alaska to Illinois, you should book around 4 weeks before departure, which saves you about 31% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 6 weeks before departure.

  • How many cities have direct flights to Illinois?

    From Alaska, there are direct flights to Illinois from 1 city. This city is Anchorage and there are 28 direct flights each week.

  • How many direct flights to Illinois are there each day?

    There are around 4 direct flights from within Alaska to Illinois every day. All flights depart in the evening.

  • How many direct flights to Illinois are there each week?

    Each week there are around 28 direct flights from within Alaska to Illinois. The most common day for departures is Monday, with 14% of flights taking off on this day.

  • How long is the flight to Illinois?

    An average nonstop flight from Alaska to Illinois takes 15h 31m, covering a distance of 2890 miles. The shortest route is Anchorage (ANC) to Chicago O'Hare Intl Airport (ORD) with an average flight time of 6h 09m.

  • How many long-haul flights are there to Illinois each week?

    There are not any long-haul (6-12 hour flight duration) or short-haul (up to 3 hour flight duration) flights to Illinois. Instead, there are 28 medium-haul flights (3-6 hour flight duration), with the most arriving from Anchorage.

  • What are the most popular destinations in Illinois?

    Based on KAYAK flight searches, the most popular destination is Chicago (84% of total searches to Illinois). The next most popular destinations are St. Louis (16%) and Peoria (0%).

Reviews of the top 4 airlines serving from Alaska to Illinois

 
Need help choosing which airline to fly with from Alaska to Illinois? 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.
7.9
Alaska AirlinesOverall score based on 13134 reviews
8.1Boarding
7.0Food
7.8Comfort
7.0Entertainment
8.5Crew
Airline reviews

Anything to make the customer experience better. Stop cancelling flights like people traveling have nothing better to do than have their life plans halted. People go to great lengths to get time off work, make plans at the end of their flights, make travel plans, go through the nightmare of checking in at busy stressful airports, make pick up arrangements only to have the rug pulled out from under them. Flying has become so miserable now!! The flights were delayed ONLY with American Airlines. The disorganization is sickening. After the flight being delayed multiple times, when the flight was finally broadcast that it was a go, EXCEPT, they were now waiting for flight attendants. They had plenty of time to plan this, what the heck?! Missed both connecting flights because it was so delayed. I vowed to never fly American Airlines again, did it and BOY was it a mistake!!! American Airlines ranks with United as two worst airlines.

2.0 MediocreAnonymous, Sep 2026
Read more Alaska Airlines reviews

Anything to make the customer experience better. Stop cancelling flights like people traveling have nothing better to do than have their life plans halted. People go to great lengths to get time off work, make plans at the end of their flights, make travel plans, go through the nightmare of checking in at busy stressful airports, make pick up arrangements only to have the rug pulled out from under them. Flying has become so miserable now!! The flights were delayed ONLY with American Airlines. The disorganization is sickening. After the flight being delayed multiple times, when the flight was finally broadcast that it was a go, EXCEPT, they were now waiting for flight attendants. They had plenty of time to plan this, what the heck?! Missed both connecting flights because it was so delayed. I vowed to never fly American Airlines again, did it and BOY was it a mistake!!! American Airlines ranks with United as two worst airlines.

Potatoes were not cooked in the pork potato meal. Flight attendants were great in first class.

I paid extra to choose my seat. I chose a window seat. I don’t know if it was a disconnect between KAYAK or the airline but when we got to the airport, the seat was changed to a middle seat. Didn’t notice it til at the gate. I called wanted a refund and was told that I didn’t choose the seat even though on my KAYAK reservation it showed seat 12 A. So I paid extra for seat selection, but didn’t get it. And also did not get a refund. I specifically pay the extra for a seat selection. I normally am very happy with Alaska Airlines. They are usually in my top three of choices.

The plane smelled like an aquarium. Many passengers noted it smelled like fish. We then sat on the plane for over 2 hours before taking off

Worst travel day of my life. First bumped from our 7am flight—that we booked to ensure enough time to get to Chicago and get ready to go to a concert. Ended up on a flight 5hours later only to arrive in Chicago and spend 2 hours sitting in the tarmac. Missed the concert ($650 in tickets) and was too late to cancel the hotel ($500). I did receive a $200 voucher for the next Alaska ticket—soooo generous 👎. Would LOVE if Alaska reimbursed the $1000+that I am out!

Only issue is that when you board last they make you check your carry on due to lack of space. Did not care for that.

5 1/2 hour trip. Nice plane. easy boarding. Could have used a bit more beverage service but it was a red eye flight and they didn't want to wake everyone.

When I booked with Kayak, I paid extra for a window seat for the long flight, so I could sleep more easily. But when I checked in, they changed my seat to a middle seat. This happened on both long flights to and from Chicago to Anchorage. For one flight, upon request they changed my seat back to a window seat. For the other, they would not and said the Alaska Airlines does not allow seat requests.....just disappointing.

To start with the plane was delayed for five hours and it messed up my whole night and the rest of my trip.we never got any notification that it was going to be late ,but they did say be at the airport early as they’are expecting long tsa lines, I usually fly delta,but my brother talked me into flying Alaska ,so i got my education the hard way.i bought three tickets for this flight and I think it was way too much for the hassle it caused me.

Plane was very cold, but other than that, it was a perfect flight

Requested an aisle seat at the gate and got it. The staff so friendly

Flight was very delayed so I was able to get on an earlier flight via stand-by. Crew communicated effectively around delay and worked to make customers comfortable. Wifi was ok, streaming TV was great. App functionality broke down once I was moved to stand-by on earlier flight.

Sat in the tarmac at O’Hare for 65 minutes. This is a regular occurrence for delta at O’Hare

Delta was fine though my flight was delayed 4 hours into LGA and my return into ORD involved a taxi of 1+ hour to the gate

It was as good as it could be. Flying is not a pleasant experience these days.

There was an unruly family behind us that made the short flight miserable!!! The cabin crew did nothing to contain it.

Flight delay was frustrating, also you cannot checkin online without delta app, web browser check-in throw errors

Got on the plane and sat there for an hour before departure.

Very large passenger too space from my own seat. Arm board couldn’t be lowered because of his size. It wads very uncomfortable trip, as the flight was full couldn’t move anywhere having back pain because of the position in which I was the entire flight.

Cramped seating for me. Luckily it wasn’t a long flight

When booking, the connection times seem fine. But in reality, my two connections were cut short by the first leg being delayed due to issues at the destination (too much traffic going into SFO, ORD) and it became extremely stressful.

Flight and crew were great. Need more legroom and do not allow seats to recline.

We arrived to Chicago nearly 30 minutes early, which was great, but then was on the ground for over an hour because the gate was not available. The issue I had was the pilot estimation was frustrating. First he said he was informed it would be 20 minutes but he said "it will probably be more like 10 minutes". After 30 minutes he came back on the comm and said it would be another 10 minutes, maybe 20. I understand he was only giving estimates but he also layered in his own gut feel. We were never told why we didn't have a gate even after our scheduled entry.

Just sat on the run way after we arrived early

Stored my cloth purse under seat in front off me as instructed. When I retrieved it, half of it was soaked, along with everything inside it. I don’t really know how that could have been prevented because the area did not look wet, but I was not happy about it.

Phx - ORD was nice 737 with starlink and the ORD - grr was ancient bare bones airbus with not even a power port lol

It was easy to board, and the staff was friendly and helpful. What could have been better is that I shouldn't have to pay extra for a seat that doesn't recline.

Was on the plane sitting longer than the actual flight in air was, boarded at 5:45p and didn't take off until 6:50p flight was only about 30 minutes long. Just was poor experience will booking more with American Airlines.

The couple in front of me were constantly talking over the announcement from the captain and this was annoying me.

The first leg of my trip the Republic Airlines aircraft was late due to a maintenance problem. Then I called United to reroute. Their reroute airline lost my bag but found it and returned it two days later. Hopefully my return trip home is better.

It was close to its perfect the flake could be took off early, landed early, didn’t have to wait for my daughter stroller luggage came out quick, very efficient, very good flight

The amount of gate changes and delays is completely unacceptable. This has happened on 3 of 4 trips between Chicago and Dallas in 2026.

The delay update was very late. I had a stressful short connection and RAN through Chicago to get to the next flight, only to find the plane wasn't at the gate yet an nobody was boarding. I would not have had to run if the delay was updated earlier.

No flight delays. No need to rebook to make connections. Enjoyed second leg of flight on Iberia.

Same the delay was not ideal and the credits to move flights was not sufficient

No food on 4.5 hour flight, wi-fi did not work. Terrible experience for a long haul flight.

The crew were diligent about ensuring that our pet dog remained in his carrier for the entire flight, as is their mandate. I wish that mandate was changed so that our poor, scared pets can be comforted during a flight, whereas service animals get to stay out and about for the whole flight. Thank you.

first leg from san diego to chicago, only had cookies for snack. 1 flavor of sparkling water chicago to washington dc had option of cookies, pretzels, or gold fish. had 2 flavors of sparkling water. 2nd flight better however the best part was there was no delays!!! Got to chicago and washington dc early. That was wonderful!!!!

Business class flight attendant was very good. But our flight was delayed two hours for a “mechanical” bathroom issue that literally took 5 minutes to fix. Our plane landed early from its previous flight but still waited for a mechanic to show up to fix an obvious minor issue for almost three hours. This caused us to miss our connecting flight. They put us up in a Days Inn that was 17 miles away from the airport that took a half hour of driving just to get to and this was at 11pm at night. Then when we finally got back on a plane after a full day delay they left our luggage back in the airport. This was an international flight, so no luggage or belongings after flying 8 hours to a different country. We will NEVER fly American Airlines again.

Check in agent was helpful and nice. Flight was OK. Our flight in Chicago was delayed 8 hours without an explination. This was our journey home. After a horrible flight experience on on the way to our vacation where our plane was diverted for an emergency medical issue, was grounded for hours, we missed our connecting flight by 25 minutes, and it took a day yo get re-booked, this was yet another bad experience that American seemed unwilling to help out with, much less compensate us for the

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