$194 Find Cheap Flights from Chicago to Alaska - Compare and Save

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 8/27. 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.
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Cheap Flights from Chicago to Alaska

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Anchorage
Anchoragenonstop$392
Fairbanks
Fairbanksnonstop$403
Anchorage
Anchoragenonstop$392
Fairbanks
Fairbanksnonstop$403

Book Cheap Chicago to Alaska Plane Tickets

 
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

Mon, Aug 24 - Mon, Aug 31
Alaska Airlines Logo
7:20 am - 11:12 am
ORD
-
ANC
6h 52mnonstop
Alaska Airlines Logo
1:29 am - 11:59 pm
ANC
-
ORD
19h 30m
1 stop
$392Alaska Airlines
Thu, Aug 27 - Thu, Sep 3
Alaska Airlines Logo
7:20 am - 11:12 am
ORD
-
ANC
6h 52mnonstop
Alaska Airlines Logo
10:28 pm - 7:40 am
ANC
-
ORD
6h 12mnonstop
$393Alaska Airlines
Mon, Aug 24 - Mon, Aug 31
Alaska Airlines Logo
7:20 am - 11:12 am
ORD
-
ANC
6h 52mnonstop
Alaska Airlines Logo
1:29 am - 7:21 pm
ANC
-
ORD
14h 52m
2 stops
$394Alaska Airlines
Mon, Sep 7 - Sun, Sep 20
American Airlines Logo
4:57 pm - 8:51 pm
ORD
-
ANC
6h 54mnonstop
American Airlines Logo
9:54 pm - 7:25 am
ANC
-
ORD
6h 31mnonstop
$397American Airlines
Mon, Aug 24 - Tue, Sep 1
American Airlines Logo
4:57 pm - 8:51 pm
ORD
-
ANC
6h 54mnonstop
American Airlines Logo
9:56 pm - 7:25 am
ANC
-
ORD
6h 29mnonstop
$402American Airlines
Mon, Sep 14 - Sat, Sep 19
United Airlines Logo
3:35 pm - 7:16 pm
ORD
-
FAI
6h 41mnonstop
United Airlines Logo
8:22 pm - 5:20 am
FAI
-
ORD
5h 58mnonstop
$403United Airlines
Sat, Aug 22 - Sun, Aug 23
Delta Logo
7:25 pm - 11:39 am
MDW
-
ANC
19h 14m
1 stop
Delta Logo
10:10 pm - 6:01 pm
ANC
-
MDW
16h 51m
1 stop
$407Delta
Tue, Sep 15 - Tue, Sep 22
Delta Logo
2:00 pm - 9:00 pm
MDW
-
ANC
10h 00m
1 stop
Delta Logo
10:10 pm - 8:48 am
ANC
-
MDW
7h 38m
1 stop
$413Delta
Wed, Aug 19 - Wed, Aug 26
Southwest Logo
12:00 pm - 9:15 pm
MDW
-
ANC
12h 15m
1 stop
Southwest Logo
11:55 pm - 5:00 pm
ANC
-
MDW
14h 05m
2 stops
$418Southwest
Wed, Aug 19 - Wed, Aug 26
Southwest Logo
10:30 am - 10:45 pm
MDW
-
ANC
15h 15m
2 stops
Southwest Logo
11:55 pm - 5:00 pm
ANC
-
MDW
14h 05m
2 stops
$423Southwest
Booking Insights

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.

How much is a round-trip flight from Chicago to Alaska?

This analysis is based on the cheapest round-trip price found on KAYAK in the last 12 months by searching for a flight from Chicago to Alaska departing in August.

Flight prices are below average for this route right now.

Flights to Alaska from Chicago usually cost between $452 and $684 in August.
The lowest price found in the past 5 days was $392 on Alaska Airlines (Aug 24-Aug 31).

What is the cheapest Chicago to Alaska flight route?

Data is based on round-trip flight searches on KAYAK over the past month.

The cheapest ticket to Alaska from Chicago found in the last 5 days was to Anchorage, at $373 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 5 days was $373.

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

The average price for all round-trip flights from Chicago to Alaska depending on the time of departure, clicked by users on KAYAK in the last 2 weeks.

The cheapest time of day to fly to Alaska is generally in the evening, when round-trip flights cost $495 on average. Morning departures are around 12% more expensive than evening flights, on average. The most expensive time of day to fly to Alaska is generally in the afternoon, which is peak travel time and where the average cost of a ticket is $868.

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.

No, with an average price for the route of $477, prices are generally cheapest when you fly direct.

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 January, when tickets cost $407 (return) on average. On the other hand, the most expensive months are March and July, when the average cost of round-trip tickets is $632 and $590 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 Saturday is the most expensive. Flying from Alaska back to Chicago, the best deals are generally found on Thursday, with Sunday 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 4 weeks before departure, which saves you about 26% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 5 weeks before departure.

Good to know

Low season

April

Cheapest flight

$194
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.

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).

Reviews of the top 4 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.
7.9
Alaska AirlinesOverall score based on 12691 reviews
7.8Comfort
8.5Crew
7.0Entertainment
8.1Boarding
7.1Food
Airline reviews

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

2.0 MediocreAnonymous, Jul 2026
ORD - CHS
Read more Alaska Airlines reviews

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.

No WiFi. Terrible food. Very long walk to the gate and from the gate after landing. Gate changed without notice.

I really hate the seat assignment at the gate. I understand it is so families can sit together but it caused me and others a lot of unnecessary stress and confusion, enough for me to not fly Alaska again. The app is so awful that it did not even update my seat assignment on the boarding pass but sent me a notification of my seat... it showed in Apple Wallet but not in the Alaska app itself. That only made the stress worse. I think most people like myself prefer to know where they are seated at check in 24 hours before so they don't have to anxiously hang out at the gate the entire time. This is not a good use of your agents time either to be dealing with all of us asking where we are sitting. You should automatically assign the multiple seat purchases to be together before they check in and fill us solo travelers in those gaps as we check in.

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!

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.

The staff was frielndly. The plane was terrible, it was too small and should be decommissioned. There were no back seat screens at all. The only beverages we had a choice from was coffee, tea or water. The only bathroom in the back was behind the flight attendant's jump seat and wasn't working. And I literally felt like I was sitting on top of the guy next to me. It was terribly hot in the plane and we had to sit on the tarmac in Chicago for 1/2 hour due to congestion in Mpls. Wouldn't they have know that before they even boarded us so that we could have sat in comfort in the terminal?

This was one of the worst flights I’ve been on in years. I upgraded to comfort and had such an uncomfortable experience. The person next to me was oversized - which I understand - however, they took up their space and mine. I could only use about 50% of my seat space to not be physically touching this person the entire flight and there was no spatial awareness. I also could not use the seat outlet because their body was obstructing it. It was very inconvenient. Their body kept touching me repeatedly during the flight and I felt very uncomfortable. To pay more for an upgraded space and then not even being able to use it was highly disappointing.

It was very cold because the air conditioner was on high power, and my son got sick.

The boarding process was terrible especially with an indirect flight Chicago to Seattle to San Diego was terrible talking about we overbooked a flight idk if I’d take this airline ever again we got off our flight from Chicago to Seattle and we traveled for business and they told us our connecting flight was over booked and their was no seats asking people to take a delayed next flight and they don’t tell anyone coughing to wear masks seats 30A-B were terrible during the flight no one wants to sit next to people coughing all around I don’t want to be sick traveling for work or get sick anytime it’s very upsetting the staff doesn’t take this stuff serious to tell them to wear masks when they see people coughing and sneezing

It was extremely hot in the cabin the entire flight, vent air was worn

Have not had a flight out or returning to Norfolk that has not required maintenance, and a gate delay. Properly staff the crew so maintenance can be performed without last minute emergencies on each flight and there is enough staff to have gates prepared for inbound flights. Staff to ensure the safety and on time service vs. profit.

My original flight was cancelled and that affected my trip and my plans and I got no compensation and customer service was hard to reach as well

The flight was delayed by a hour and I wish they had communicated it sooner. No issues on the plane, it did take a while for food to come.

Know that the movies that you are going to be offered are the oldest be rated movies they could possibly get. They may have one or two new movies that they keep advertising but when you’re flying 15 hours, there is nothing to see past the first new movie.

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

Horrible! Several delays and then was cancelled! I spent over 24 hours in the airport and was unable to get a hotel or food voucher.

Boarded early; and arrived home 40 mins early. After a long flight, it’s nice to be back home early. These flights have no amenities; no snacks. So need to bring your own

A long delay. Don't travel late in the day.

Super friendly with lots of drink options an entertainment. Friendly crew.

I had my flight of Cedar Rapids. THen Chicago to Boston. Flight out of Cedar rapids was delayed by 12 hrs. Had to drive to Chicago to catch my flight

Long delays to board due to mechanical issues with plane.

Flight was delayed, boarded, sat at the gate for more than 30 minutes, left the gate then waited on the pad for another 30 to 60 minutes then returned to the gate, deboarded and was cancelled... alternative flight was not booked automatically. Waited in line for 30 minutes but fortunately an alternate flight to a different destination was found ... no thanks to the travel agent used by kayak

The flight from Milwaukee to Dallas was great the staff absolutely amazing. After that EVERYTHING WENT DOWN HILL!!! ABSOLUTELY HORRIBLE!!! WILL NOT FLY THIS AIRLINE AGAIN

I was very unhappy with the lack of communication from the cockpit. It took close to a half an hour before we took off after the doors were closed, and we got no announcements as to progress. It would be nice to get some acknowledgement of the situation and updates as to when we are taking off.

The seat was not even cleaned. It has full of cookie crums probably from last flight's passenger. Its basic expectation that, seats are clean.

Very turbulent flight, no drinks, very little service, unorganized boarding, gate changed multiple times

The flight was delayed significantly. Communication during the flight was abrupt and caused some panic as we were navigating turbulence. It was also too loud and every announcement felt startling. The flight attendants did not offer any assurances and I felt unsettled most of the flight. The seats, floor and tray table was very dirty. The seat next to me was broken and the passenger sitting there was very uncomfortable. He had a spring in his back and his seat made terrible squeaking noises through the flight.

Significant delays on my trip to Chicago and my trip back to NY

Delayed by 5 hours and I had to wit in the airport for more than 6+ hours.

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.