ANC - CHI

$183 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 6/7. 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, 0 bags

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
Travelers love KAYAK
41,299,237 searches in the past 7 days on KAYAK

Save 24% 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.

Everything you should know

Cheapest round-trip
$360
Typical prices: $618-$461
Alaska Airlines
Mon 5/18Sun 5/24
ANC - ORD • Non-stop
Cheapest non-stop
$367
Typical prices: $592-$472
American Airlines
Thu 6/4Mon 6/8
ANC - ORD • Non-stop
Advice from real travelers
AI-powered summary based on content written by travel experts. AI can make mistakes.
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
Cheapest • from $360 (round-trip)
Best reviews • 7.9 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Nonstop flights
You can fly direct with Alaska Airlines, American Airlines and United Airlines. Average duration is 6h 19m
Direct flights
Direct flights
+1
+1
Direct flights
Direct flights
+1
Top routes
Cheapest
Most popular
Insights
Insights
Insights
Insights
When to book
in advance
Our data shows that travelers who book at least 4 weeks in advance save around 29% compared to booking last minute.
Insights
Insights
Insights
Insights
When to travel
Cheapest • 31% price drop
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
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!
Flight Deals
Booking Insights
Expert advice
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

Mon, May 18 - Sun, May 24
Alaska Airlines Logo
11:08 pm - 8:25 am
ANC
-
ORD
6h 17mnonstop
Alaska Airlines Logo
6:00 am - 12:04 pm
ORD
-
ANC
9h 04m
1 stop
$360Alaska Airlines
Mon, May 18 - Sun, May 24
Alaska Airlines Logo
7:40 am - 11:59 pm
ANC
-
ORD
13h 19m
1 stop
Alaska Airlines Logo
6:00 am - 12:04 pm
ORD
-
ANC
9h 04m
1 stop
$363Alaska Airlines
Thu, Jun 4 - Mon, Jun 8
American Airlines Logo
9:50 pm - 7:23 am
ANC
-
ORD
6h 33mnonstop
American Airlines Logo
5:02 pm - 8:41 pm
ORD
-
ANC
6h 39mnonstop
$367American Airlines
Fri, Jun 5 - Mon, Jun 8
American Airlines Logo
7:00 am - 8:11 pm
ANC
-
ORD
10h 11m
1 stop
American Airlines Logo
5:02 pm - 8:41 pm
ORD
-
ANC
6h 39mnonstop
$377American Airlines
Thu, May 21 - Thu, May 28
Alaska Airlines Logo
11:08 pm - 8:25 am
ANC
-
ORD
6h 17mnonstop
Alaska Airlines Logo
9:00 am - 9:36 pm
ORD
-
ANC
15h 36m
2 stops
$381Alaska Airlines
Wed, May 27 - Wed, Jun 10
Alaska Airlines Logo
11:08 pm - 8:25 am
ANC
-
ORD
6h 17mnonstop
Alaska Airlines Logo
8:05 pm - 8:40 am
ORD
-
ANC
15h 35m
1 stop
$383Alaska Airlines
Tue, May 26 - Mon, Jun 8
Delta Logo
1:55 am - 1:45 pm
ANC
-
ORD
8h 50m
1 stop
Delta Logo
7:01 am - 9:16 pm
ORD
-
ANC
17h 15m
1 stop
$387Delta
Mon, May 18 - Sun, May 24
Delta Logo
6:00 am - 5:56 pm
ANC
-
MDW
8h 56m
1 stop
Delta Logo
6:23 am - 6:38 pm
MDW
-
ANC
15h 15m
1 stop
$387Delta
Sat, Aug 29 - Tue, Sep 1
Alaska Airlines Logo
3:45 pm - 1:22 pm
ANC
-
ORD
18h 37m
1 stop
Alaska Airlines Logo
8:00 am - 11:44 am
ORD
-
ANC
6h 44mnonstop
$389Alaska Airlines
Thu, May 21 - Thu, May 28
Southwest Logo
10:25 pm - 2:40 pm
ANC
-
MDW
13h 15m
2 stops
Southwest Logo
12:10 pm - 10:45 pm
MDW
-
ANC
13h 35m
1 stop
$392Southwest
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.

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

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

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 $397 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 Sunday, as it's usually the priciest day. When flying back from Chicago, Friday is the cheapest day to fly and Saturday 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 August, where tickets cost $158 (return) on average. On the other hand, the most expensive months are January and February, where the average cost of round-trip tickets is $408 and $357 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.

No, with an average price for the route of $498, prices are generally cheapest when you fly direct.

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 29% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 13 weeks before departure.

Expert advice

Expert advice for your flight from Anchorage to Chicago

 
AI-powered summary based on content written by travel experts. AI can make mistakes.
KAYAK teamed up with top travel experts to share the best tips for your journey.
Our travel experts
Harriet Baskas

Harriet Baskas

Expert on American Airlines and Alaska Airlines

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.

Stefanie Waldek

Stefanie Waldek

Expert on United Airlines and ORD

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.

Ramsey Qubein

Ramsey Qubein

Expert on ANC

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.

Good to know

Low seasonJanuary
Cheapest flight$183
Best time to beat the crowds but there is an average 7% increase in price.
Most popular time to fly and prices are also 9% 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 $183 for a one-way ticket and $360 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?

    Hawaiian Airlines, Alaska Airlines, 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?

    SkyTeam, oneworld, and Star Alliance are the airline alliances operating flights between Anchorage and Chicago, with SkyTeam 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 $402 and an overall rating of 7.9, Alaska Airlines is the most popular choice. Delta is also a great choice for the route, with an average price of $396 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 $304 or less one-way and $574 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.
7.9
Alaska AirlinesOverall score based on 12314 reviews
7.1Food
8.1Boarding
7.8Comfort
7.0Entertainment
8.5Crew
Airline reviews

I'm not sure if you are going to ask me about the check in process. I could not get my boarding pass, so I had to stop at the American desk before security. I also had a difficult time downloading the app with the confirmation code for the two flights.

6.0 GoodAnonymous, Feb 2026
BNA - ORD
Read more Alaska Airlines reviews

I'm not sure if you are going to ask me about the check in process. I could not get my boarding pass, so I had to stop at the American desk before security. I also had a difficult time downloading the app with the confirmation code for the two flights.

The tray wasn’t cleaned, it had crumbs from the last flight Other than that it was very comfortable by

Kayak wouldn’t refund me for a flight I was trying to cancel through Kayak. Alaska airlines said I had to cancel through Kayak. I called the customer service line and they couldn’t refund the flight that I booked through Kayak either. You stole my money. You will be hearing from my lawyer.

Worst first/business class I have ever flown after 75 years on planes. Barely acceptable seats, terrible food, uninterested attendants, unavailable WiFi. I’ll never fly this airline again.

Service was great! 👍 Seats were small and absolutely not enough leg and feet room!!!

Dropping off of the checked bags took way longer than it should have. The agent for the pre-tagged and ready to drop off line was gone and didn't come back for about 15 minutes. The other bag check lines were barely moving. Agents were standing around and not much was getting done. Everything else about the flight was great.

Check in online didn't accept my confirmation number so i could only check in with assistance at the airport and ended up with s creepy middle seat.

It was the most expensive Alaska Airlines ticket I’ve ever purchased. I had a middle seat with no legroom or space compared to any other middle seat I’ve hadThere was a silver box under the seat that took up 70% of my legroom on the most narrow 737 max the crew flat out would not help they would not help with bags they would not help with garbage there was no coffee,It was definitely not one of my better experiences on Alaska.

Flight was delayed several times then eventually cancelled which caused issues with our hotel, car rental and tickets to planned event. We also spent unplanned expense with Lyft to and from the airport which was frustrating. Customer care was not present during whole time at the airport.

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.

The agent at check in and at the gate were less than thrilled to be at work. I'm not a fan of Kayak's placement on the plane. I got put in the middle seat and none of my preferences were used.

In ATL they have two sets of departure screens. Follow what is on your airline's departure board - the ATL Airport Authority departure board had completely incorrect details about the gate assignment for my flight, which would have made me miss boarding.

Flight was delayed it was hot while sitting on the plane, one engine was working on the plane until they had to do some jimmy rigging down the runway in order for the other engine to charge up. It was ridiculous

The flight was very good and the staff was very friendly and helpful!

The only thing I would say is we tried to get on a standby earlier flight, but with our fair we couldn’t. That seems senseless to leave with open seats..

Very easy to use and convenient, you can perform any action within the same portal

In a world of delays, Delta was on time both ways! Boarding was fast and efficient. Staff was friendly. AND wifi worked.

WiFi didn’t work. Flight delayed 3 hours Crew members were illiterate Seat lean back did not work.

Flight was delayed, we could have been notified earlier and in a consistent manner. App was not refreshing for another passenger to get the latest flight status. We could have stayed and waited at the hotel instead of waiting at the airport had we known the flight was going to delayed for more than 5 hours. The toilet is too tight, and needs to be cleaned more frequently (every hour). The entertainment screen froze, the touch screen not responding to touch. We were upgraded to comfort, it is more comfortable than regular economy seats.

This wasn't my experience with Delta. It was just the Pegasus flight. Seats were very hard. Staff was kinda rough. Not very nice. Charged me for snacks. For a 4 hour flight I would've expected more.

Standard flight with a drinks and a snack- overall very quick flight. The flight attendants were very strict, bordered on rude.

Delayed - weather wasn't bad at either end. Also sat on tarmac in ORD.

boarded early to only find out that flight would sit at gate for 45 min to an hour. Landed in chicago and sat on runway for over an hour before got to gate. Total delay was extensive for a 45 min flight door to door.

The flight was significantly delayed. The inbound flight from EWR was delayed departing because of mechanical problems. My original departure from CLT was 5:28 pm but due to the delay of the inbound flight, after arrival, deplaning, cleaning, boarding, we did not push back from the gate until 9:00 pm. Once in the air, the flight was smooth and what was originally supposed to be an arrival in ORD at 7:30 pm local time turned out to be 9:35 pm.

The flight I was supposed to be on was supposed to take off at 1:50 from State College. It was delayed over and over and over again until somehow I had to rebook on a flight that was supposed to have left State College at 8 am that morning but didn't end up taking off until almost 6 pm. Not only was this completely unacceptable, the "token from United" was a 15 dollar meal voucher that has to be used by today. I would personally like some miles added to my account for this inconvenience. I was in transit for 8 hours from the time I arrive at State College Aiport to when I got home. I was supposed to be home at 3 pm and I returned at 8 pm. Unacceptable. I have not been on an on Time united flight in nearly 5 years.

newer aircraft, ability to connect my headset via blue tooth for entertainment.

Very comfortable flight, snacks and drinks were good, good communication from crew. Could have used a little more information on timing of boarding for group 5

Great flight. Got to watch a movie. Smooth flight and early arrival at ORD.

It was better than excellent. The staff in Mason City were great. The young woman that pushed my wheelchair did more than could be expected of her. She came from India 17 years ago. I don't remember her name.

After arriving in Chicago, we were taxiing for 1.5 hours with infrequent and untruthful updates about the amount of time it would take to arrive at the gate. Minimally, the team could have provided timing expectations that were more truthful, especially one their original expectations were not met.

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

Information on your arrival and departure airports