ANC - CHI

$159 Find Cheap Flights from Anchorage to Chicago

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Anchorage to Chicago departing on 8/25. 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 Chicago

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Anchorage to Chicago, 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 Anchorage to Chicago, as well as popular online travel agencies
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Flights Deals

Cheap Flights from Anchorage to Chicago (ANC-CHI)

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

Thu, Oct 2 - Sat, Oct 11
Alaska Airlines Logo
11:25 pm - 8:40 amANC-ORD
6h 15mnonstop
Alaska Airlines Logo
8:10 am - 12:08 pmORD-ANC
6h 58mnonstop
$318Alaska Airlines
Find Deal
Thu, Sep 18 - Sun, Sep 21
American Airlines Logo
9:53 pm - 7:17 amANC-ORD
6h 24mnonstop
American Airlines Logo
5:01 pm - 8:48 pmORD-ANC
6h 47mnonstop
$319American Airlines
Find Deal
Thu, Oct 2 - Sat, Oct 11
Hawaiian Airlines Logo
11:25 pm - 8:40 amANC-ORD
6h 15mnonstop
Hawaiian Airlines Logo
8:00 am - 3:34 pmORD-ANC
10h 34m1 stop
$328Hawaiian Airlines
Find Deal
Fri, Oct 10 - Sat, Oct 18
Delta Logo
12:30 am - 5:18 pmANC-ORD
13h 48m1 stop
Delta Logo
2:00 pm - 10:43 pmORD-ANC
11h 43m1 stop
$338Delta
Find Deal
Wed, Oct 22 - Tue, Oct 28
Delta Logo
9:45 pm - 8:55 amANC-MDW
8h 10m1 stop
Delta Logo
7:10 pm - 12:51 amMDW-ANC
8h 41m1 stop
$338Delta
Find Deal
Thu, Oct 9 - Sat, Oct 18
Alaska Airlines Logo
1:47 am - 5:01 amANC-ORD
24h 14m1 stop
Alaska Airlines Logo
8:10 am - 12:08 pmORD-ANC
6h 58mnonstop
$341Alaska Airlines
Find Deal
Fri, Oct 10 - Sat, Oct 18
Delta Logo
9:45 pm - 12:45 pmANC-ORD
12h 00m2 stops
Delta Logo
7:37 am - 3:19 pmORD-ANC
10h 42m1 stop
$343Delta
Find Deal
Thu, Oct 23 - Mon, Oct 27
United Airlines Logo
9:04 pm - 6:13 amANC-ORD
6h 09mnonstop
United Airlines Logo
4:05 pm - 7:59 pmORD-ANC
6h 54mnonstop
$361United Airlines
Find Deal
Sat, Oct 11 - Sat, Oct 18
Hawaiian Airlines Logo
11:11 pm - 8:40 amANC-ORD
6h 29mnonstop
Hawaiian Airlines Logo
8:10 am - 12:08 pmORD-ANC
6h 58mnonstop
$377Hawaiian Airlines
Find Deal
Wed, Oct 22 - Mon, Oct 27
United Airlines Logo
9:04 pm - 6:13 amANC-ORD
6h 09mnonstop
United Airlines Logo
4:05 pm - 7:59 pmORD-ANC
6h 54mnonstop
$398United Airlines
Find Deal
Expert advice

Expert advice for your flight from Anchorage to Chicago

 
Snippets provided in this section are AI-generated based on a summarization of KAYAK-commissioned articles. The articles are presented as-is, for general informational purposes only, and may not be up-to-date. The opinions contained in the articles are original to the author and reflect their authentic experience, which may vary significantly from the experience of others.
KAYAK teamed up with top travel experts to share the best tips for your journey.
Airlines
American Airlines

American's Main Cabin Extra includes early boarding and complimentary alcoholic drinks.


Download the American Airlines app for access to inflight entertainment content.

Alaska Airlines

Alaska's 20-minute baggage guarantee offers a discount or 2,500 miles if delayed.


Alaska's Premium Class offers extra legroom and complimentary drinks on flights over 350 miles.

United Airlines

United's Economy Plus offers up to 6 inches more legroom than standard economy seats.


Purchase Priority Boarding to secure overhead bin space, placing you in Zone 2.

Airports
ANC

For late evening flights, expect busy security lines at ANC. Arrive early to avoid delays, especially for the 11pm departures.

Read more about ANCby Ramsey Qubein
ORD

The CTA Blue Line connects ORD to downtown Chicago in about 45 minutes, offering a reliable alternative to driving.

Read more about ORDby Stefanie Waldek
Our travel experts
Harriet Baskas

Harriet Baskas

Expert on American Airlines and Alaska Airlines

Harriet Baskas

Harriet Baskas

Harriet is an award-winning journalist who is happiest in an airport or an unusual museum. Her stories about airports, air travel, and the business of travel have appeared on NBC News, CNBC, USA TODAY, The Points Guy and other outlets. She is the creator of the StuckatTheAirport.com blog and the author of nine books. When not out on the road or exploring the latest airport amenities, she’s home in Seattle getting ready for the next adventure.

Read more
Stefanie Waldek

Stefanie Waldek

Expert on United Airlines and ORD

Stefanie Waldek

Stefanie Waldek

Stefanie Waldek is a freelance space, travel, and design writer based in Saratoga Springs, NY. Her words have appeared in Space.com, Travel + Leisure, Condé Nast Traveler, Architectural Digest, and House Beautiful, among other publications. An expert in aviation and expedition cruising, Stefanie is frequently up in the air or on the sea, likely en route to Antarctica or the Arctic.

Read more
Ramsey Qubein

Ramsey Qubein

Expert on ANC

Ramsey Qubein

Ramsey Qubein

An avid traveler and aviation expert who has visited 173 countries, all 50 states and seven continents, Ramsey Qubein flies nearly 400,000 miles a year. As a North Carolina-based freelance journalist for publications including Conde Nast Traveler, Forbes, USA Today and Bloomberg among others, he explores the latest trends in aviation, hospitality, cruises and business.

Read more
Booking Insights

KAYAK's insights & trends for Anchorage to Chicago flights

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

What is the cheapest Anchorage to Chicago flight route?

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

Our data shows that the cheapest route for a return flight from Anchorage to Chicago cost $376 and was between Anchorage (ANC) and Chicago O'Hare Intl Airport (ORD). On average, the best prices are found if you fly this route. The average price for a return flight for this route is $376.

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

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

If you are looking for a flight deal from Anchorage to Chicago, look for departures on Tuesdays and avoid leaving on a Saturday, as it's usually the priciest day. When flying back from Chicago, Wednesday is the cheapest day to fly and Thursday is the most expensive.

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

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Anchorage to Chicago, 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 Anchorage to Chicago is November, where tickets cost $395 (return) on average. On the other hand, the most expensive months are March and December, where the average cost of round-trip tickets is $649 and $642 respectively.

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

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 1 stop layover the cheapest option at $395 on average.

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

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from Anchorage to Chicago, 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 Anchorage to Chicago, you should book around 4 weeks before departure, which saves you about 50% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 17 weeks before departure.

Good to know

Low seasonMarch
Cheapest flight$159
Best time to beat the crowds but there is an average 24% increase in price.
Most popular time to fly and prices are also 25% lower on average.
Flight from Anchorage to Chicago O'Hare Airport

When to book flights from Anchorage to Chicago

Are your dates flexible? Find out the best times to travel from Anchorage to Chicago based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs for booking flights from Anchorage to Chicago

  • What is the cheapest flight from Anchorage to Chicago?

    In the last 3 days, the lowest price for a flight from Anchorage to Chicago was $159 for a one-way ticket and $318 for a round-trip.

  • Do I need a passport to fly between Anchorage and Chicago?

    No

  • Which airports will I be using when flying from Anchorage to Chicago?

    Anchorage is served by only 1 airport and there are 2 airports in Chicago. You will leave Anchorage from Anchorage and you will be arriving in Chicago at one of these airports: Chicago Midway or Chicago O'Hare Intl.

  • Which airlines offer Wi-Fi service onboard planes from Anchorage to Chicago?

    Alaska Airlines, Hawaiian Airlines, American Airlines, and Delta offer inflight Wi-Fi service on the Anchorage to Chicago flight route.

  • Which aircraft models fly most regularly from Anchorage to Chicago?

    The Boeing 737 MAX 9 is the aircraft model that flies most regularly on the Anchorage to Chicago flight route.

  • Which airline alliances offer flights from Anchorage to Chicago?

    oneworld, and Star Alliance are the airline alliances operating flights between Anchorage and Chicago, with oneworld being the most commonly used for this route.

  • On which days can I fly direct from Anchorage to Chicago?

    There are nonstop flights from Anchorage to Chicago on a daily basis.

  • Which is the best airline for flights from Anchorage to Chicago, Alaska Airlines or Delta?

    The two airlines most popular with KAYAK users for flights from Anchorage to Chicago are Alaska Airlines and Delta. With an average price for the route of $537 and an overall rating of 8.0, Alaska Airlines is the most popular choice. Delta is also a great choice for the route, with an average price of $548 and an overall rating of 8.0.

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

    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 Anchorage to Chicago.

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

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

    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 to Chicago with an airline and back to Anchorage with another airline.

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

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

KAYAK’s top tips for finding a cheap flight from Anchorage to Chicago

  • Looking for a cheap flight? 25% of our users found flights on this route for $295 or less one-way and $527 or less round-trip.

Prefer to fly direct from Anchorage to Chicago?

 
Direct data is based off flight results for the next 60 days. Find direct flights from all airlines flying direct from Anchorage to Chicago.
Find which airlines fly direct from Anchorage Airport to Chicago, which days they fly and book direct flights.

Direct departures

Anchorage to Chicago

Monday

Alaska Airlines, American Airlines, United Airlines

Alaska Airlines, American Airlines, +1 more

Tuesday

Alaska Airlines, American Airlines, United Airlines

Alaska Airlines, American Airlines, +1 more

Wednesday

Alaska Airlines, American Airlines, United Airlines

Alaska Airlines, American Airlines, +1 more

Thursday

Alaska Airlines, American Airlines, United Airlines

Alaska Airlines, American Airlines, +1 more

Friday

Alaska Airlines, American Airlines, United Airlines

Alaska Airlines, American Airlines, +1 more

Saturday

Alaska Airlines, American Airlines, United Airlines

Alaska Airlines, American Airlines, +1 more

Sunday

Alaska Airlines, American Airlines, United Airlines

Alaska Airlines, American Airlines, +1 more

See more direct flights

Direct returns

Chicago to Anchorage

Monday

Alaska Airlines, American Airlines, United Airlines

Alaska Airlines, American Airlines, +1 more

Tuesday

Alaska Airlines, American Airlines, United Airlines

Alaska Airlines, American Airlines, +1 more

Wednesday

Alaska Airlines, American Airlines, United Airlines

Alaska Airlines, American Airlines, +1 more

Thursday

Alaska Airlines, American Airlines, United Airlines

Alaska Airlines, American Airlines, +1 more

Friday

Alaska Airlines, American Airlines, United Airlines

Alaska Airlines, American Airlines, +1 more

Saturday

Alaska Airlines, American Airlines, United Airlines

Alaska Airlines, American Airlines, +1 more

Sunday

Alaska Airlines, American Airlines, United Airlines

Alaska Airlines, American Airlines, +1 more

See more direct flights

Reviews of the top 3 airlines serving from Anchorage to Chicago

 
See real verified KAYAK customer reviews for airlines flying from Anchorage to Chicago. 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 Anchorage to Chicago? 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
7.1Entertainment
8.1Boarding
8.5Crew
7.8Comfort
Airline reviews

I was pleasantly surprised to discover that Alaskan Airlines allows normal leg space in the economy class cabin, offers free movies and other entertainment programs via WiFi. The staff was friendly and worked hard to make this long flight enjoyable.

10.0 ExcellentAnonymous, Jul 2025ANC - DEN
Read more Alaska Airlines reviews

I was pleasantly surprised to discover that Alaskan Airlines allows normal leg space in the economy class cabin, offers free movies and other entertainment programs via WiFi. The staff was friendly and worked hard to make this long flight enjoyable.

On time would have been a hell of a lot better!!

Cancelled my flights with only 6 hours notice, then offered alternate flights that arrived 1:30 AM next day.

Flight from New Orleans to Seattle to Anchorage was delayed for 3 hours My flight from Seattle to Anchorage was not rescheduled. I had to call the airlines to tell them to get a flight from Seattle to Anchorage they finally got me a flight If I hadn’t been aware of this problem I don’t know how long I would of waited in Seattle to get a flight to Anchorage!!!!!! Return trip from Anchorage to New Orleans in Seattle to New Orleans I was at the right gate when I realized something was wrong they had changed the gate without notifying the change l finally made it on time with minutes to spare & exhausted

It was fine. 2 hour delay due to mechanical issue. I understand issues will occur, just wish instead of Capt repeatedly telling us we will be getting off the ground “momentarily” they would just be honest and either say they have no idea-or it’s going to be a few hours! All in all FAs are usually pretty nice :)

Could have service kiosks, had to find a gate with an attendant

The flight was short and smooth. The crew was friendly and courteous.

Booked a first class ticket from Anchorage to Seattle but was denied complimentary access to Alaska Lounge as our 1500 mile flight wasn’t long enough’

Way too warm for that length of flight!! If the pretzel bag gets any smaller, there won't even be any pretzels to eat!! Crew didn't talk. $99 just for an aisle seat is ludicrous!! Probably won't fly Alaska again.

Boarding for Alaska Airlines is always chaotic with many people crowding the gates. Arriving in on Alaska in Los Angeles is always interesting since there is never a gate available. So the planes are often parked all the way out on the west side of the airport while waiting for the gate to be cleared of the departing plane. This flight was no exception.

Delayed and took off even later than the scheduled delay time

For a 69 year old with health problems I had the worse experience, no wheelchair when I entered a lady told me to sit and wait while a gentleman told me I had to walk to the Delta station, which I did. I had a carry on and a bag, and I was traveling with my service dog, which was on his carrier and the lady charged me for my carry on luggage, beside all the waiting cause of the delay, I had to walk to get my luggage cause no wheelchair showed up, I am so disappointed. I will get in touch with the company. I got home at 3:00 am, not good for my health situation.

Great experience on Delta. Staff from baggage check to flight attendants were very courteous and professional. My only issue was a personal preference for pretzels instead of the chips and cookies that were offered.

There was no problems, just a little uncomfortable with seats that do not lay back a little

Always good but we must do something about people in rows ahead of you that don't put their seats back up when they are suppose to. And It's rough to not be able to even lean over to get something out of my purse.

Flight was delayed, 30+ bags had to be gate checked. Crew were very friendly!

Everything was good until we were boarding our connection flight in Atlanta, we were told to gate check our carry-on, but when we got inside the plane, there was plenty of room in the overhead.

Did not know my son and I had different seating arrangements. He was fine, but it was disappointing.

Flight was canceled, and no effort was made to help with rebooking, no hotel vouchers, no car transportation and minimal food voucher and most places for food were closed by the time the voucher was given. Waited for 3 hours for bags. Simply the worst travel experience I have ever had

Food was surprisingly good but the WiFi was not great

Weather delay in Chicago?. No sense of urgency to make connection in Chicago for our connecting flight that wasn't delayed. Connection was missed.

Overall it was good. I missed my connection but I was put on another flight.

Overall a very poor experience - booked premium economy tickets but due to last minute flight delays , all my itinery went for a toss and had to fly economy class with no access to lounge or any compensation by united airlines to make up for the flight delays . i had expected better experience than that from united.

It was fine, definitely older planes with no charging or anything. There’s no entertainment set up on board, but it is nice that they allow you to access the in flight entertainment from your phone without having to pay for the Wi-Fi and they do offer free texting.

I liked that the flight was nonstop from ORD to CIU for $200 round trip.

While the staff was pleasant and helpful, the following observations are for your awareness. There was some delay on the tarmac on take off and landing. The paid lunch/food offerings were limited. Entertainment was only available on WiFi at a cost.

The first flight was better in terms of the aircraft.

Smooth flight. Boarding was chaotic. Could not hear the gate agent over the intercom. People were lined up in the wrong lines. Groups one and two were told to board through line one and group 3 through line 2. All very confusing. Once in the air, the flight was smooth. There was no entertainment option on this aircraft, even though it was a larger aircraft.

Overall poor for me I paid extra for seats with leg room and my regional flights exit row seats have less leg room then the others that's money that could have been saved and on my final flight home the flights air was not operating it was unbearably hot in the cabin I will be contacting United and filing a DOT complaint

There's just no way to sit fully upright and comfortably in these seats. There needs to be 2 more inches of room, and that's not something that only one person on the flight needs - the whole flight needs 2 more inches of room. If that means you sell 6 less seats, so be it. It's too close for anyone. Forcing people to pay for "premium" economy just to get "barely enough space to breathe" isn't really an answer to that.

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

Information on your arrival and departure airports

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