ANC - CHI

$186 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 7/13. 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
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Everything you should know

Cheapest round-trip
$373
Typical prices: $502-$358
Alaska Airlines
Thu 9/3Mon 9/7
ANC - ORD • Non-stop
Cheapest one-way
$186
Typical prices: $271-$385
American Airlines
Mon 7/13
ANC - ORD • Non-stop
Advice from real travelers
AI-powered summary based on content written by travel experts. AI can make mistakes.
Alaska Premium Class adds legroom and drinks; United Economy Plus adds legroom.
American Main Cabin Extra includes early boarding and drinks; Alaska has a bag guarantee.
Expert advice
Expert advice
Expert advice
Expert advice
Top airlines
Cheapest • from $373 (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
Top layover airports
Cheapest • Avg $391 (round-trip)
Shortest trip • 8h 24m (one-way)
Insights
Insights
Insights
Insights
When to book
in advance
Our data shows that travelers who book at least 5 weeks in advance save around 47% compared to booking last minute.
Insights
Insights
Insights
Insights
When to travel
Cheapest • 35% price drop
Most popular
Good to know
Good to know
+1
+1
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+1
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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

Thu, Sep 3 - Mon, Sep 7
Alaska Airlines Logo
10:28 pm - 7:40 am
ANC
-
ORD
6h 12mnonstop
Alaska Airlines Logo
7:20 am - 11:12 am
ORD
-
ANC
6h 52mnonstop
$373Alaska Airlines
Sun, Jul 5 - Sun, Jul 12
Alaska Airlines Logo
9:24 pm - 6:40 am
ANC
-
ORD
6h 16mnonstop
Alaska Airlines Logo
12:59 am - 4:41 am
ORD
-
ANC
6h 42mnonstop
$376Alaska Airlines
Thu, Aug 27 - Tue, Sep 1
Alaska Airlines Logo
10:28 pm - 7:40 am
ANC
-
ORD
6h 12mnonstop
Alaska Airlines Logo
2:22 pm - 8:51 pm
ORD
-
ANC
9h 29m
1 stop
$383Alaska Airlines
Thu, Aug 27 - Sun, Aug 30
Alaska Airlines Logo
10:28 pm - 7:40 am
ANC
-
ORD
6h 12mnonstop
Alaska Airlines Logo
7:20 am - 11:12 am
ORD
-
ANC
6h 52mnonstop
$386Alaska Airlines
Thu, Aug 27 - Tue, Sep 1
Delta Logo
10:30 pm - 4:17 pm
ANC
-
ORD
14h 47m
1 stop
Delta Logo
12:29 pm - 9:00 pm
ORD
-
ANC
11h 31m
1 stop
$393Delta
Thu, Sep 24 - Sun, Sep 27
Delta Logo
6:00 am - 6:11 pm
ANC
-
MDW
9h 11m
1 stop
Delta Logo
7:13 pm - 12:45 am
MDW
-
ANC
8h 32m
1 stop
$393Delta
Fri, Sep 25 - Mon, Sep 28
American Airlines Logo
9:54 pm - 7:25 am
ANC
-
ORD
6h 31mnonstop
American Airlines Logo
7:09 am - 7:13 pm
ORD
-
ANC
15h 04m
1 stop
$396American Airlines
Thu, Sep 3 - Mon, Sep 7
Delta Logo
6:00 am - 8:30 pm
ANC
-
ORD
11h 30m
2 stops
Delta Logo
6:00 am - 11:39 am
ORD
-
ANC
8h 39m
1 stop
$398Delta
Fri, Sep 25 - Mon, Sep 28
Delta Logo
10:10 pm - 12:34 pm
ANC
-
MDW
11h 24m
2 stops
Delta Logo
7:13 pm - 12:45 am
MDW
-
ANC
8h 32m
1 stop
$398Delta
Sun, Sep 6 - Sat, Sep 12
American Airlines Logo
9:56 pm - 7:25 am
ANC
-
ORD
6h 29mnonstop
American Airlines Logo
4:53 pm - 8:49 pm
ORD
-
ANC
6h 56mnonstop
$399American Airlines
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 September.

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 $419 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 $492, 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 5 weeks before departure, which saves you about 47% 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 Alaska Airlines and American 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$186
Best time to beat the crowds but there is an average 9% 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 5 days, the lowest price for a flight from Anchorage to Chicago was $186 for a one-way ticket and $373 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, Delta, Hawaiian 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, Star Alliance, and oneworld 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 $397 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 $301 or less one-way and $610 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 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.
7.9
Alaska AirlinesOverall score based on 12517 reviews
8.5Crew
7.0Entertainment
8.1Boarding
7.8Comfort
7.1Food
Airline reviews

The flight kept getting delayed due to a maintenance issue. That happens, but there is no excuse for changing the gate FIVE TIMES, including one time nearly all the way across SeaTac. After we were delayed for 3+ hours, they did send us (via email) a $12 meal voucher...except you can't find a $12 meal anywhere in that airport, unless you consider a bag of M&M's and a bottle of water a meal. The plane had one problem after another but finally took off 4.5 hours late. This caused us to miss our hotel shuttle at ORD (they didn't run past midnight and it was 3 am) so we had to wait 25 minutes and pay for an Uber. I did get a $50 flight voucher from Alaska...big deal. Barely covers my Uber ride that I shouldn't have needed.

2.0 MediocreAnonymous, Jun 2026
SEA - ORD
Read more Alaska Airlines reviews

The flight kept getting delayed due to a maintenance issue. That happens, but there is no excuse for changing the gate FIVE TIMES, including one time nearly all the way across SeaTac. After we were delayed for 3+ hours, they did send us (via email) a $12 meal voucher...except you can't find a $12 meal anywhere in that airport, unless you consider a bag of M&M's and a bottle of water a meal. The plane had one problem after another but finally took off 4.5 hours late. This caused us to miss our hotel shuttle at ORD (they didn't run past midnight and it was 3 am) so we had to wait 25 minutes and pay for an Uber. I did get a $50 flight voucher from Alaska...big deal. Barely covers my Uber ride that I shouldn't have needed.

It was good. Too long for older people. Service and support was great! Friendly crew!

Ok, but nothing special. Long flight with no blanket/pillow set.

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.

Be on time? When not on time a circling for over an hour offer more than 1 bag of chips to the passengers? It was a 7 hour flight by the time we got done.

Five hour delays every hour, I wish it were all at once

Flight delayed four separate times. I’m now one hour hours late to landing.

worst flight ever from Delta, it got delayed and kept on delaying..

Should never have had to go to Detroit from Orlando back to Tennessee!

Got rerouted from a straight flight from Orlando to Atlanta to Knoxville to a flight from Orlando to Detroit to Knoxville! Seriously!! Flight delay out of Detroit! Long day for what should have been a pretty easy travel day!

Two delays on two separate planes with parts they could not easily find and replace.

Checkin was good, fllight ws good. Onlly complaint is lack of foot on 6 hour flight from Seattle to Boston. Snacks were flimsy - chips and cookies. could have offered something more substantial for such a long flight. I know you can buy food in airport but for the price you pay for a ticket, they should step up for the passengers.

Only beverages were offered to first class and I thought the flight attendant could have also served the Delta Comfort as well instead of sitting down and staring at her phone and walking past all of us to the back of the plane to charge her phone more. There was a complete lack of turbulence and was safe enough for flights attendant to walk around in the front of the plane, collect trash and serve a few people water and turn off the seat belt light. Also didn’t enforce people putting their seats into the upright position and allowed two passengers to remain reclined during landing. They seemed out to lunch completely. Usually my experience on Delta is much better.

Long story short, it was one of the better flight experiences I've had in some time when compared with other airlines.

Over 5 hour delay with minimal updates or ability to standby for alternative flights. During boarding and 1 hr+ wait for takeoff, seats were drenched w water from air conditioning condensation and always leftover crumbs on carpet and seats

Boarded early, left early, arrived 40 mins early! A win win for me!

These airplanes should be illegal. The seats are two tight, it is a safety issue. Wheelchair support was ridiculously slow. We almost missed our flight.

This flight is a quick way to get to Chicago, but a bit expensive.

O’hsre taxi and deboarding took 40 minutes. Needed 20 minutes extra time between connecting flights to avoid running through terminal.

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.

The flight attendants were extremely sourly and borderline rude. I did not feel appreciated as an AA customer once.

The flight from LA to Chicago was smooth and service was very good overall.

The Mario was so helpful and provided amazing customer service however l have being waiting for a callback for almost a week now and have not heard anything further after l informed them l wanted to change my date of traveling because of my hospital appointment even send them proof and l was unable to use manag your booking on their website is a bit frustrating and l would appreciate an update on My request as soon as possible. And have called them times without numbers no response

Awful, tons of delays, I got into Chicago multiple hours late meaning I hit the very traffic I tried so desperately to avoid. Just empty apologies from American Airlines text alerts. Trash behavior from a trash airline.

They lost my baggage and I am still struggling to the information and update

Requested early boarding to disinfect seat, tray table, etc. before general boarding. Instructed to board after wheelchair passengers. Waited on jet bridge behind 12 wheelchair passengers. Stopped immediately after entering plane to wait for gate agent in rear of plane cleaning a seat that was wet, got to my row and found both seats adjacent to mine already occupied, with the lack of room making it impossible for me to clean my own space and defeating the purpose of my boarding early. Cleaned the armrests and tray table as best I could.

The wifi experience is awful. I had to try again and again, taking over 30 minutes, to connect to the wifi. I had to watch the same two ads over and over until I was finally successful. Once connected, it was anything but "high speed" and disconnected at least three times during the flight.

It was good, the staff was great, and the food, was as usual, tea and biscuit. Bathroom was clean, and the plane was clean as well.

Very good I can’t complain one bit. Thank you American Airlines for making my flight enjoyable and safe!

The staff and service on American Airlines were truly outstanding. I had requested wheelchair assistance for my mother due to her knee issues, and the team went above and beyond every step of the way—from boarding in Boston to our arrival in Chicago. Their care, professionalism, and attentiveness made the entire experience smooth and stress-free. I’m very grateful for the support they provided.

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

Information on your arrival and departure airports