$180 Find Cheap Flights from Chicago to Alaska

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Chicago to Alaska departing on 9/6. 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

KAYAK searches hundreds of travel sites at once for deals on flights to Alaska

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Alaska, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Alaska, as well as popular online travel agencies
Travelers love KAYAK
41,299,237 searches in the past 7 days on KAYAK

Save 20% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Bundle and saveSave money when you bundle your flight + hotel.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Flights Deals
Useful Info
Flights Deals

Best Alaska Flight Deals from Chicago

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Anchorage
Anchoragenonstop$358
Fairbanks
Fairbanks1 stop$423
Anchorage
Anchoragenonstop$358
Fairbanks
Fairbanks1 stop$423

Cheap Flights from Chicago to Alaska

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

Wed, Sep 3 - Sun, Sep 7
Alaska Airlines Logo
8:40 am - 12:21 pmORD-ANC
6h 41mnonstop
Alaska Airlines Logo
11:25 pm - 8:40 amANC-ORD
6h 15mnonstop
$358Alaska Airlines
Find Deal
Sun, Sep 21 - Sun, Sep 21
Alaska Airlines Logo
7:00 am - 1:22 pmORD-ANC
9h 22m1 stop
Alaska Airlines Logo
11:25 pm - 8:40 amANC-ORD
6h 15mnonstop
$362Alaska Airlines
Find Deal
Sun, Sep 21 - Mon, Sep 22
Delta Logo
2:18 pm - 11:15 pmORD-ANC
11h 57m1 stop
Delta Logo
6:10 am - 7:47 pmANC-ORD
10h 37m1 stop
$372Delta
Find Deal
Fri, Sep 12 - Wed, Sep 17
Delta Logo
6:45 pm - 1:00 amMDW-ANC
9h 15m1 stop
Delta Logo
6:10 am - 6:07 pmANC-MDW
8h 57m1 stop
$378Delta
Find Deal
Wed, Aug 13 - Wed, Aug 20
Hawaiian Airlines Logo
12:59 am - 4:37 amORD-ANC
6h 38mnonstop
Hawaiian Airlines Logo
11:25 pm - 8:40 amANC-ORD
6h 15mnonstop
$396Hawaiian Airlines
Find Deal
Mon, Aug 4 - Tue, Aug 12
American Airlines Logo
5:06 pm - 8:42 pmORD-ANC
6h 36mnonstop
American Airlines Logo
9:54 pm - 7:14 amANC-ORD
6h 20mnonstop
$435American Airlines
Find Deal
Thu, Sep 11 - Tue, Sep 16
American Airlines Logo
11:54 am - 7:08 pmORD-ANC
10h 14m1 stop
American Airlines Logo
9:53 pm - 7:17 amANC-ORD
6h 24mnonstop
$440American Airlines
Find Deal
Wed, Oct 8 - Wed, Oct 15
United Airlines Logo
4:10 pm - 7:57 pmORD-ANC
6h 47mnonstop
United Airlines Logo
9:04 pm - 6:13 amANC-ORD
6h 09mnonstop
$476United Airlines
Find Deal
Mon, Aug 4 - Mon, Aug 11
Hawaiian Airlines Logo
6:15 pm - 2:01 amORD-ANC
10h 46m1 stop
Hawaiian Airlines Logo
12:29 am - 12:07 pmANC-ORD
8h 38m1 stop
$479Hawaiian Airlines
Find Deal
Wed, Oct 8 - Wed, Oct 15
United Airlines Logo
2:17 pm - 10:42 pmORD-ANC
11h 25m1 stop
United Airlines Logo
9:04 pm - 6:13 amANC-ORD
6h 09mnonstop
$486United Airlines
Find Deal
Useful Info

KAYAK's insights & trends for Chicago to Alaska flights

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

What is the cheapest Chicago to Alaska flight route?

The cheapest price for flight routes found by users searching on KAYAK in the last 2 weeks for round-trip flights from Chicago to Alaska.

The cheapest ticket to Alaska from Chicago found in the last 72 hours was to Anchorage, at $396 round-trip. The most popular route is from Chicago O'Hare Intl Airport (ORD) to Anchorage (ANC), and the cheapest round-trip airline ticket found on this route in the last 72 hours was $396.

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

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 3 stops layover the cheapest option at $803 on average.

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

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Chicago to Alaska, 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 Chicago to Alaska is April, when tickets cost $391 (return) on average. On the other hand, the most expensive months are December and June, when the average cost of round-trip tickets is $668 and $579 respectively.

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

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

For Chicago to Alaska, Wednesday is the cheapest day to fly on average and Sunday is the most expensive. Flying from Alaska back to Chicago, the best deals are generally found on Monday, with Saturday being the most expensive.

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

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from Chicago to Alaska, 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 Chicago to Alaska, you should book around 3 weeks before departure. For the absolute cheapest price, our data suggests you should book 6 weeks before departure.


Good to know

Low seasonJanuary
High seasonJuly
Cheapest flight$180
Best time to beat the crowds with an average 16% drop in price.
Most popular time to fly with an average 11% increase in price.
Flight from Chicago O'Hare Airport to Anchorage

FAQs - booking Alaska flights

  • I want to visit Juneau, Alaska, from Chicago. How should I get there?

    If you’d like to fly from Chicago to Alaska’s capital city of Juneau, start with a flight from Chicago O’Hare Airport (ORD) or Chicago’s Midway Airport (MDW) to Anchorage Airport (ANC). Upon arriving in Anchorage, you can take a nonstop flight to Juneau International Airport (JNU). Alternatively, you can take a layover flight from O’Hare Airport or Midway Airport to Juneau International Airport with a stopover at Seattle-Tacoma Airport (SEA).

  • Are there any nonstop flights from Chicago to Alaska?

    If you’d like a non-stop flight from Chicago to Alaska, fly out of Chicago O’Hare International Airport (ORD). United Airlines and Alaska Airlines offer nonstop service from O’Hare International Airport to the Ted Stevens Anchorage International Airport (ANC). Chicago’s Midway Airport (MDW) only offers layover flights from Chicago to Alaska.

  • I’m flying from Chicago to Alaska to visit Denali National Park. Where should I fly to?

    If you want to visit Denali National Park in Alaska from Chicago, consider flights from Chicago O’Hare Airport (ORD) or Chicago Midway Airport (MDW) to Fairbanks International Airport (FAI). United Airlines provides non-stop flight service, while both Delta and Alaska Airlines provide layover flights with a stop at Seattle-Tacoma International Airport (SEA). From Fairbanks, a train goes directly to Denali National Park, taking around 4 hours.

  • Are there any flights from Chicago to the Arctic region of northern Alaska?

    Although there aren’t any direct flights from Chicago to the Arctic region of Alaska, you can reach that area with multiple flights. First, fly from either Chicago O’Hare Airport (ORD) or Chicago Midway Airport (MDW) to Anchorage Airport. From Anchorage Airport (ANC), you can take nonstop flights to the Arctic towns of Barrow (around 2 hours), Deadhorse (about 1h 40min), Kotzebue (around 1h 30min), and Nome (about 1h 30min).

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

    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 Chicago to Alaska.

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

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

    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 Chicago to Alaska 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 Chicago to Alaska?

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

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

    The cheapest time of day to fly to Alaska is generally in the afternoon, when round-trip flights cost $436 on average. Morning departures are around 3% more expensive than evening flights, on average. The most expensive time of day to fly to Alaska is generally in the morning, which is peak travel time and where the average cost of a ticket is $571.

Top tips for finding cheap flights to Alaska

  • If you’d like to relax before a long flight from Chicago to Alaska, Chicago O’Hare Airport (ORD) offers multiple lounges with daily passes. The American Airlines Admirals Clubs are in Concourses G, H, K, and L, while the United Clubs are in Concourses B, C, and F.
  • Both Chicago’s O’Hare Airport and Chicago Midway Airport (MDW) offer facilities and services for passengers with reduced mobility. These include accessible parking, accessible entrances, accessible bathrooms, and wheelchair assistance upon request.
  • If you’re looking for eco-friendly flights from Chicago to Alaska, both United Airlines and American Airlines are committed to net-zero carbon emissions by 2050. Alaska Airlines aims for the same by 2040. All three airlines seek to improve their fuel efficiency, as well.
  • Carry-on luggage policies for American Airlines, Delta, and United Airlines flights from Chicago to Alaska include a small personal item and a larger carry-on item that doesn’t exceed 22 lb. Their checked bag allowance includes up to two bags for a modest fee, with each bag measuring up to 62 linear inches.
  • Are you looking to save money on your flight from Chicago to Alaska? If you’re flexible on time, one-stop or two-stop flights tend to be cheaper than nonstop flights to Alaska. Sun Country Air flights have one stop at Minneapolis St Paul Airport (MSP), while Alaska Airlines stops at San Francisco Airport (SFO) and Seattle-Tacoma Airport (SEA).

Top 5 airlines serving from Chicago to Alaska

 
See real verified KAYAK customer reviews for airlines flying from Chicago to Alaska. 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 Chicago to Alaska? 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
Alaska AirlinesOverall score based on 10000 reviews
7.1Food
7.8Comfort
7.1Entertainment
8.1Boarding
8.5Crew
Airline reviews

It sucks, flight delays at FAT caused us to miss a day at lodge and overnight in Seattle. Flight delays coming home also. Never again

2.0 MediocreAnonymous, Jun 2025PSG - JNU
Read more Alaska Airlines reviews

It sucks, flight delays at FAT caused us to miss a day at lodge and overnight in Seattle. Flight delays coming home also. Never again

The plane was late taking off. We sat on the plane at least 45-60 minutes before moving away from the gate. Im 5’9” and 185lbs and there is no room in those seats. On top of that you shoehorn a waterbuffalo of a woman in the middle seat to where her sweaty rolls and arms were well into my seat and touching me the whole time. It was either that or press against the opposite arm rest and get hit by the beverage cart and every single person who walked by.

So much better coming back to Seattle than my trip TO Chicago. This crew actually communicated with the passengers!! Rebecca, one of the crew, stopped and visited with me about sign language. She should get a bonus of some kind!! She's a very neat gal!! It was still warm inside the plane, but it was packed! I still think you could do better than those teeny tiny pretzels! These were spicy and tasted terrible! All in all, still a better ride coming home. Go Seahawks!!

Arrival delay waiting for another flight to be towed and deboarded

PAID First class. No use of lounge in Phoenix (should have a code share). Bags checked and not marked first class, asked attendant who stated on mark gold members. Last bag out of carousel. When you pay extra, expect that...wifi was rebooted and not functioning to allow internet access. Food and cree were very good.

Very Large person sitting next to me and taking up a lot of space including mine

There was no sense of urgency to get us to our destination on time. There’s just no such thing with this airline. It’s not my fault, they don’t have enough help. They sure as hell charge you enough for everything Nothing like being nickel and dimed to death. Money for bags money to choose a seat. You gotta be made for money to fly this airline.

Waited for an hour to take off with no reason for delay.

Three hour flight so snacks and basic drinks unless you pre buy as usual. Didn’t do my emtertainment as was tired after 23 hours of travel. You have to use your own device on US flights if travelers aren’t aware so if you only use your cell phone that can be small. Crew are great.

It was very good. I love flying with Alaska air.

Great service. Flight was delayed while we sat on the runway for a couple of hours. Weather related. Staff made is very bearable. The steward servicing the first class cabin was exceptional. Thank you! 💗

5 hours of delay that could've been much shorter if Delta had taken the 1 hour delay they imposed on the flight before boarding to run any of the plane checks required for flight to find the hydraulic issue that required nearly 3 hours to fix. $24 of meal credit buys a sandwich and a soft drink. Poor communication within the terminal about what gate we'd be re-boarding from and when we'd be re-boarding.

Amazing flight! I have never noticed the uniforms of the attendants before in twenty years of flying except today when one female had the most amazing dress on. It was beautifully designed and showed she was in charge. I never dreamed I would google who designed Delta uniforms . The ultimate compliment is when another woman admires your outfit. . I hope your designer puts it on the market

It would be nice if was given wires ear buds. Overall was a good experience was able to sleep on the plane

My flight was 6 pm 6/6. Every hour they delayed it again - air condition issues then no pilot then the crew had worked too many hours and cancelled the flight at 11 pm. Sent customers to NJ a 45 minutes uber ride to a hotel. Had to be back by 5 am for a 7 am flight and again no pilot etc with another three hours of delays.

The entertainment and wifi mostly didn't work on this flight.

Terrible entertainment system - kept freezing and audio kept cutting out. Snacks were mediocre at best for a 5 hour flight.

The check in and bag drop off for Sky Priority members is slow. The Clear security was also slow - a TSA issue.

I am still upset that my bag was lost on a recent trip to Rome ; we were inconvenienced and out €150 Euros ; delta has refused to reimburse us

I am very bothered by the events today. I can't believe the flight attendants allowed someone to take my seat and made me move. It was embarrassing. I was in the right. The lady just didn't want move. I can't believe delta would allow this to stand and disrespect my rights as a passenger. The lady complained about her leg and that she couldn't move. Firstly somehow she was able to make it to row 24. Not sure how much her leg could have hurt. Secondly, I'm in plenty of pain myself. I just finished chemotherapy a several weeks ago. My body is constantly sore. Yet deltas flight attendants didn't appropriately protect my rights. In the end they found me a seat on the plane but I want to understand how delta can operate this way. They in essence allowed a bully to get their way.

Flight was canceled with no voucher of any kind and next available flight was two days later.

Boarding was chaotic. Microphone not working properly and second agent was distracted from task with baggage and late arrivals.

I DID NOT GO TO HAWAII ON HAWAIIAN AIRLINES. YOU DID NOT INFORM ME THAT BY CHOOSING BASIC ECONOMY, I MIGHT BE REQUIRED TO FLY STANDBY. I AM ELDERLY AS WAS MY COMPANION WHO IS ALSO SEVERELY DISABLED AND THERE WOULD BE NO WAY WE COULD TRAVEL ON STANDBY. THEY TOLD ME THAT ALL OF THE BASIC ECONOMY SEATS HAD BEEN SELECTED BY OTHER PASSENGERS AND WE HAD TO PAY AN ADDITIONAL $942 TO GET A SECURED SEAT ON THE PLAN AND, IN SPITE OF THE ADDITIONAL COST, WE WERE NOT ALLOW US TO AMEND OUR TRAVEL PLANS TO EXTEND OUR VACATION. ULTIMATELY, THE FLIGHT WAS DELAYED. WE WERE OFFERED A REFUND IF WE CANCELED OUR TRIP ALTOGETHER WHICH WE DID. IT IS YOUR DUTY TO INFORM YOUR CUSTOMERS OF THE POTENTIAL PROBLEMS THEY MAY FACE, AND YOU DID NOT DO SO. I WILL NOT UTILIZE YOUR SERVICES EVER AGAIN.

It was very pleasant. The staff and crew are very polite.

On time. Alaska upgraded seat comfort with memory foam seat covers with head rests

the people at the counter, NEED TO BE MORE HELPFUL. we had three suitcases to check in and we were not trying to be an INCONVENIENCE TO YOUR clerks. but she was not helpful and made our trip back home memorable but not IN A GOOD WAY. Sadly to say, you guys need to teach to be and to go above and beyond to help THE CUSTOMER BY ANY MEANS POSSIBLE. they need to leave aside whatever they are going thru in their lives, THEIR WORK DEMANDS THAT OF THEM, IF NOT THEY ARE NOT IN THE JOB THEY SUPPOSED TO.

Because the airport is under construction and because Hawaiian air just changed terminals we missed boarding out flight by 5 minutes. That cost me a night in an airport hotel and several hours of rebooking to make it to my destination. Costumers need to know that airport construction is a problem and they need to add an hour to deal with the air train delays from Federal Circle.

Half of my family members didn’t make it because they involuntary bumped off . And their seats where given away

Hawaiian Airlines staff is always professional & quick & easy check in & boarding process

Customer service by Susan of Alaskan Air was outstanding. We missed our flight out of JFK. She got us rebooked the following day. Way to go Susan.

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

Had a short delay once we boarded the aircraft in Chicago, but it was fixed in no time flat then we were on our way. The pilot was able to make up the time lost and we landed 5 minute later then schedualed . Great service

Our seats were all the way in back of the plane,

The seats on this flight were almost roomy enough to be the basic amount needed for human existence. I think my favorite part of this flight was it landed at an A gate, which was the most palatial part of Sea-Tac I've ever seen - a massive improvement from the S gates.

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.

You were more on time than United. I'm so over united delays.

The meals were mediocre and the alcohol selection was poor. I enjoyed the selection of movies and other entertainment.

I chatted with the captain before the flight, and similarly during the welcome announcement, he warned of a turbulent flight that may impact the in-flight service. However, once at altitude, he announced that the weather changed and he immediately turned off the seatbelt sign. But it appeared the cabin crew had already decided to take off this flight. They remained seated and then just chatted in the galley. The flight was fully catered, but only first class received service.

My flight attendant was attentive! The elderly person next to me was flatulent and the flight attendant could see that I was in distress and brought me some face masks

My boarding pass wouldn't pull up in the app very easily and had to really dig through my email. That caused a delay in TSA..

I had a TERRIBLE experience with the AA crew. I believe it was disability-related. It’s unlikely I will fly AA again.

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

Cabin class types available on flights to Alaska

Cabin classes available on flights to Alaska. Prices are the lowest found on KAYAK over the last 7 days. Price and availability is not guaranteed.

Not what you’re looking for? Find thousands of other hotels, flights, car rentals and package deals with KAYAK.