ANC - CHI

$125 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 10/16. 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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Flight 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

Sat, Nov 1 - Fri, Nov 7
Delta Logo
6:00 am - 5:18 pmANC-ORD
8h 18m1 stop
Delta Logo
7:37 am - 4:22 pmORD-ANC
11h 45m1 stop
$270Delta
Find Deal
Sat, Nov 1 - Fri, Nov 7
Delta Logo
8:15 pm - 10:45 amANC-MDW
11h 30m1 stop
Delta Logo
7:10 pm - 12:51 amMDW-ANC
8h 41m1 stop
$270Delta
Find Deal
Fri, Oct 31 - Fri, Nov 7
Delta Logo
12:30 am - 4:11 pmANC-ORD
12h 41m2 stops
Delta Logo
6:00 pm - 1:59 amORD-ANC
10h 59m1 stop
$275Delta
Find Deal
Fri, Oct 31 - Fri, Nov 7
Delta Logo
12:30 am - 5:55 pmANC-MDW
14h 25m2 stops
Delta Logo
7:10 pm - 12:51 amMDW-ANC
8h 41m1 stop
$275Delta
Find Deal
Fri, Oct 10 - Sat, Oct 18
United Airlines Logo
11:49 pm - 1:12 pmANC-ORD
10h 23m1 stop
United Airlines Logo
4:10 pm - 7:57 pmORD-ANC
6h 47mnonstop
$313United Airlines
Find Deal
Wed, Oct 15 - Mon, Oct 20
United Airlines Logo
9:04 pm - 6:13 amANC-ORD
6h 09mnonstop
United Airlines Logo
4:10 pm - 7:57 pmORD-ANC
6h 47mnonstop
$318United Airlines
Find Deal
Sat, Oct 11 - Fri, Oct 17
Alaska Airlines Logo
11:11 pm - 8:40 amANC-ORD
6h 29mnonstop
Alaska Airlines Logo
7:00 am - 8:48 pmORD-ANC
16h 48m1 stop
$328Alaska Airlines
Find Deal
Thu, Oct 9 - Sat, Oct 18
Alaska Airlines Logo
1:47 am - 5:01 amANC-ORD
24h 14m1 stop
Alaska Airlines Logo
8:20 am - 12:18 pmORD-ANC
6h 58mnonstop
$331Alaska Airlines
Find Deal
Sat, Oct 11 - Fri, Oct 17
Hawaiian Airlines Logo
4:34 pm - 6:24 amANC-ORD
10h 50m1 stop
Hawaiian Airlines Logo
6:00 am - 2:15 pmORD-ANC
11h 15m1 stop
$335Hawaiian Airlines
Find Deal
Mon, Jan 12 - Sun, Feb 8
Hawaiian Airlines Logo
1:15 am - 1:04 pmANC-ORD
8h 49m1 stop
Hawaiian Airlines Logo
7:45 am - 4:17 pmORD-ANC
11h 32m1 stop
$338Hawaiian Airlines
Find Deal

Everything you should know

Our travelers' advice
AI-generated summary based on content written by travel experts
Alaska's Premium Class offers extra legroom and drinks.
Expect busy security lines for late evening flights at ANC.
Expert advice
Expert advice
Expert advice
Expert advice
Top airlines
Delta
Cheapest • from $270 (round-trip)
Alaska Airlines
Best reviews • 8.0 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Top routes
ANC-ORD
Cheapest
ANC-ORD
Most popular
Insights
Insights
Insights
Insights
When to book
4 weeks
in advance
Our data shows that travelers who book at least 4 weeks in advance save around 44% compared to booking last minute.
Insights
Insights
Insights
Insights
When to travel
November
Cheapest • 24% price drop
November
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
Cheapest round-trip
$270
Overall average: $425
Delta
Sat 11/1Fri 11/7
ANC - ORD • 1 stop
Cheapest non-stop
$318
Typical prices: $345-452
United Airlines
Wed 10/15Mon 10/20
ANC - ORD • Non-stop
Start a new search
KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to Chicago!
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?

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

The cheapest return flight from Anchorage to Chicago costs $295 on the route between Anchorage (ANC) and Chicago O'Hare Intl Airport (ORD). It is also the most popular route.

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 Sunday 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 $684 and $644 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 $330 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 44% 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$125
Best time to beat the crowds but there is an average 32% increase in price.
Most popular time to fly and prices are also 24% 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 $125 for a one-way ticket and $270 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, Delta, and American Airlines 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 8 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 $523 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 $544 and an overall rating of 7.9.

  • 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 $210 or less one-way and $405 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

American Airlines, United Airlines

American Airlines, United Airlines

Tuesday

American Airlines, United Airlines

American Airlines, United Airlines

Wednesday

American Airlines, United Airlines

American Airlines, United Airlines

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

American Airlines, United Airlines

American Airlines, United Airlines

Tuesday

American Airlines, United Airlines

American Airlines, United Airlines

Wednesday

American Airlines, United Airlines

American Airlines, United Airlines

Thursday

American Airlines, United Airlines

American Airlines, United Airlines

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 4 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
8.5Crew
7.1Entertainment
7.8Comfort
7.1Food
8.1Boarding
Airline reviews

Why was I charged for a glass of wine on one flight and not on another? Why no movie or TVs? It was a long flight.

10.0 ExcellentLeslie, Aug 2025SEA - ORD
Read more Alaska Airlines reviews

Why was I charged for a glass of wine on one flight and not on another? Why no movie or TVs? It was a long flight.

We received a check-in reminder the day before the flight, and it listed the flight at a later time. Correct flight number, same seats, etc. for 3 hours later. I called the airline to confirm and they had no record of the email. The info was wrong, and we would have missed our flight if we'd assumed it was correct. I want to know where/how we received this incorrect info.

My experience would’ve been great because we were on a new plane, but they said as we boarded that the plane would be too new to have WiFi, which to me is unreasonable - newer planes should def have WiFi! It was a 5 hour flight from Anchorage to San Fran and because there was no WiFi, I had to take an unexpected half day off work, which was super annoying because I had a lot to do and we only found out a few minutes before takeoff.

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.

I was very pleased with this trip from Anchorage to Seattle and Seattle to Billings. Wheelchair assistance was rendered and gratefully accepted. Unlike my outbound flights to Seattle I did not have long, painful walks on a bad knee to get to airport gates. My thanks to the Alaska staff.

Horrible. Boarded late, sat on the tarmac for over an hour, missed my connecting flight and had to spend a day in the Seattle airport. I won’t be flying Hawaiian again.

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.

The flight was very smooth. The crew was very friendly.

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!!

Perfect flight both ways. On time, courteous staff, plane comfortable and cool. Best domestic flights I’ve had in awhile.

Really low quality food especially for an international flight. The crew also was surprisingly unpleasant except couple of ladies. I know we were not in first class but that’s no reason to treat customers as less.

Flight delayed for two and half hours and then canceled altogether due to mechanical issues. No mechanic onsite to fix so had to send one from LAX.

Crew was good. The reservation got mixed up and they didn't have my TSA number. I am also a Silver Medallion and wasn't able to use Sky Priority.

Delta made it easy, comfortable and timely. The crew was fantastic.

This route with Delta always has delays or is cancelled. Aircrafts seem smaller and older. I fly Delta quite a bit - haven’t had issues with the international flights. But this route has always been the troublesome one

Three seats in first class were broken and while they were able to still acommodate us it was looking very touch and go and they had others they could not acommodate

Mechanic delay in addition to a 2 hour change in takeoff time was frustrating.

Delayed due to thunderstorms and no in-flight service due to rough weather — both of which are out of Delta’s control. Flight was good overall.

The flight attendants in SLC were rude. I arrived 40 minutes early to gate. Ticket said I needed check in for seat assignments and tried check in and attendants said they weren’t doing it. And proceeded to never call me to give me a ticket so when time to board I received the very last seat. Please relay to employees to do their job better..,

First class ticket. They ran out of food and I sat hungry watching the others eat

They we able to seat my companion and I next to each other. Plane’s temperature was very cool. Willl be more prepared on return trip.

All was good and they were able to seat my travel companion next to me. Thank you.

Like the ample leg room. May as well not bother with snacks if it's only a two ounce bag of pretzels. Didn't use the entertainment option. Was there one?

What an amazing flight. I haven’t experienced this level of service in a flight in years. This will be the only way to fly to Hawaii for me in the future.

Kayak sold me a ticket after check in time. Could not check in. Could not get on flight.

Love you guys are so friendly and kind and wonderful

Agents talk too fast over intercom. I know it’s memorized and we’ve all heard it before. Just slow down a little. Stop charging for checked bags. I was pleased to get my bags promptly at each end of my flight.

Everything was great except having to check in at Alaska. That was a surprise and took extra time and effort. Should have been explained somewhere maybe on the HA electronic ticket.

It was clean and the crew was great. I wish the chairs could recline just a little more and you would provide small pillows for people with bad backs. My back is fused and a little support would be great.

There was no food available for this red eye... one little waffle cookie for a 6+ hour flight... thank God I was able to sleep some

Flight attendant in first class gave poor service (like he didn't want to be there) and food was awful. We sat waiting for gate upon arrival over 45 mins.

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.

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

Information on your arrival and departure airports

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