ANC - CHI

$179 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 9/1. 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
Hawaiian Airlines Logo
11:25 pm - 8:40 amANC-ORD
6h 15mnonstop
Hawaiian Airlines Logo
8:20 am - 12:08 pmORD-ANC
6h 48mnonstop
$358Hawaiian Airlines
Find Deal
Thu, Oct 2 - Sat, Oct 11
Hawaiian Airlines Logo
11:25 pm - 8:40 amANC-ORD
6h 15mnonstop
Hawaiian Airlines Logo
7:00 am - 1:22 pmORD-ANC
9h 22m1 stop
$368Hawaiian Airlines
Find Deal
Sat, Oct 11 - Sat, Oct 18
Alaska Airlines Logo
11:31 pm - 8:45 amANC-ORD
6h 14mnonstop
Alaska Airlines Logo
8:20 am - 12:08 pmORD-ANC
6h 48mnonstop
$377Alaska Airlines
Find Deal
Thu, Oct 2 - Sat, Oct 11
Alaska Airlines Logo
11:25 pm - 8:40 amANC-ORD
6h 15mnonstop
Alaska Airlines Logo
10:00 am - 11:44 pmORD-ANC
16h 44m2 stops
$378Alaska Airlines
Find Deal
Fri, Oct 10 - Sat, Oct 18
Delta Logo
12:40 am - 4:47 pmANC-ORD
13h 07m2 stops
Delta Logo
6:13 pm - 1:45 amORD-ANC
10h 32m1 stop
$383Delta
Find Deal
Fri, Oct 10 - Sat, Oct 18
Delta Logo
12:40 am - 4:34 pmANC-ORD
12h 54m2 stops
Delta Logo
1:35 pm - 11:15 pmORD-ANC
12h 40m2 stops
$388Delta
Find Deal
Thu, Aug 14 - Fri, Aug 22
American Airlines Logo
9:54 pm - 7:14 amANC-ORD
6h 20mnonstop
American Airlines Logo
5:09 pm - 8:49 pmORD-ANC
6h 40mnonstop
$396American Airlines
Find Deal
Thu, Aug 14 - Fri, Aug 22
American Airlines Logo
9:54 pm - 7:14 amANC-ORD
6h 20mnonstop
American Airlines Logo
1:24 pm - 11:05 pmORD-ANC
12h 41m1 stop
$406American Airlines
Find Deal
Sun, Nov 2 - Tue, Nov 4
United Airlines Logo
9:07 pm - 6:09 amANC-ORD
6h 02mnonstop
United Airlines Logo
4:05 pm - 7:59 pmORD-ANC
6h 54mnonstop
$476United Airlines
Find Deal
Sun, Nov 2 - Tue, Nov 4
United Airlines Logo
9:07 pm - 6:09 amANC-ORD
6h 02mnonstop
United Airlines Logo
2:40 pm - 10:56 pmORD-ANC
11h 16m1 stop
$486United 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
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.

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.

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 Alaska Airlines and American 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
Useful Info

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 $416 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 $416.

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 Mondays 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 $385 (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 $639 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 $197 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. For the absolute cheapest price, our data suggests you should book 17 weeks before departure.

Good to know

Low seasonMarch
High seasonNovember
Cheapest flight$179
Best time to beat the crowds but there is an average 25% increase in price.
Most popular time to fly and prices are also 26% 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 $179 for a one-way ticket and $358 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, American Airlines, Hawaiian 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 $516 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 $535 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 $293 or less one-way and $619 or less round-trip.

Prefer to fly 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
See more direct flights

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

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’

4.0 OkayLorri, Jun 2025ANC - SEA
Read more Alaska Airlines reviews

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.

The would have rated higher, but I asked for a cup of coffee twice and never got one. Later found the crew sitting in the back having a meal and visiting. Just saying.

Broke the wheels of my luggage. Should be more gentle with other peoples belongings. Very upset about needing a new suitcase before Christmas.

I was able to upgrade easily on the way home to first class. No problems with luggage. Efficient time management getting us to our destination on time

The airline was great. What was annoying as hell were the inaccurate emails from KAYAK telling me the boarding gate changed and the date of my flight was 1 day later then the actual flight 😡

We're an hour late to leave airport due to not enough crew to load baggage onto the aircraft. Missed my connecting flight. The customer service was helpful, but the second plane was also late to depart and was very hot inside. Not a great experience, but the crew did the best they could.

I had wonderful flight. Only negative was the entertainment. Because there was not any entertainment on the plane.

Good flight times. The app didn’t show all available seats when checking in. I thought I had to pay for an exit row to have a seat but there were actually 42 seats left. Then I had to get a refund and getting ahold of a customer care representative who was able to do that was very very difficult.

Great service. Flight was delayed while we sat on the runway for a couple of hours. Weather related. Staff made is very bearable. The steward servicing the first class cabin was exceptional. Thank you! 💗

5 hours of delay that could've been much shorter if Delta had taken the 1 hour delay they imposed on the flight before boarding to run any of the plane checks required for flight to find the hydraulic issue that required nearly 3 hours to fix. $24 of meal credit buys a sandwich and a soft drink. Poor communication within the terminal about what gate we'd be re-boarding from and when we'd be re-boarding.

Amazing flight! I have never noticed the uniforms of the attendants before in twenty years of flying except today when one female had the most amazing dress on. It was beautifully designed and showed she was in charge. I never dreamed I would google who designed Delta uniforms . The ultimate compliment is when another woman admires your outfit. . I hope your designer puts it on the market

It would be nice if was given wires ear buds. Overall was a good experience was able to sleep on the plane

My flight was 6 pm 6/6. Every hour they delayed it again - air condition issues then no pilot then the crew had worked too many hours and cancelled the flight at 11 pm. Sent customers to NJ a 45 minutes uber ride to a hotel. Had to be back by 5 am for a 7 am flight and again no pilot etc with another three hours of delays.

The entertainment and wifi mostly didn't work on this flight.

Terrible entertainment system - kept freezing and audio kept cutting out. Snacks were mediocre at best for a 5 hour flight.

The check in and bag drop off for Sky Priority members is slow. The Clear security was also slow - a TSA issue.

I am still upset that my bag was lost on a recent trip to Rome ; we were inconvenienced and out €150 Euros ; delta has refused to reimburse us

I am very bothered by the events today. I can't believe the flight attendants allowed someone to take my seat and made me move. It was embarrassing. I was in the right. The lady just didn't want move. I can't believe delta would allow this to stand and disrespect my rights as a passenger. The lady complained about her leg and that she couldn't move. Firstly somehow she was able to make it to row 24. Not sure how much her leg could have hurt. Secondly, I'm in plenty of pain myself. I just finished chemotherapy a several weeks ago. My body is constantly sore. Yet deltas flight attendants didn't appropriately protect my rights. In the end they found me a seat on the plane but I want to understand how delta can operate this way. They in essence allowed a bully to get their way.

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.

The crew were very nice. The Chocolate is good and v there’s no entertainment. Thanks

The crew were very nice. I would have appreciated a pillow for comfort. I had a special meal that was sloppy, but the salad was great. Thanks

The plane was in Moline all night. Consequently, we assumed an on time departure at 8:15am. Unfortunately, and as is the normal case with United in Moline, we departed 2.5 hours late. When the crew came, it was discovered that there was very little heat in the plane. Seems this should have been checked hours before the crew arrived. Then when we boarded and the plane was to be de-iced, the United de-icing truck was not working! We awaited the American Airlines truck. All of this caused us to miss our connection in Chicago. My suggestion is never take United Airlines flight from Moline. We have been disappointed 80% of the time and have vowed to not take United again from Moline.

Most miserable flight ever. We waited almost 2 hours on the runway because the flight was oversold. American offered $1200 credit. Then there was some nonsense about weight distribution. Ridiculous. No food for 8 plus hours on the flight. I will be writing a letter.

The flight was 2 hour delayed, otherwise everything was excellent. The delay was due to the hourly limit requirement so given that as a reason, I'm happy with the flight!

Not sure the logic of the boarding in Groups. I was loaded first on the aisle. Then the guy in the middle. Then the guy by the window. Constantly holding up the other people boarding behind them with us blocking the aisle and this happened in most of the other rows

To start, I’d like to say that every American Airline personnel I interacted with on the ground, especially flight crew, was very friendly and did their best to help me out. Despite this, however, my experience with the airline was an entire mess. The 7:19 PM flight was heavily delayed due to weather, and pushed to 10:30 AM the next morning. Because of this, I had to spend the night inside of the airport. At some point later in the night, I got an email saying that the flight had been canceled. I called the support number, and the representative on the other line told me that the flight was still on and that I didn’t need to rebook. The next morning, no one came to the gate to open the door for the crew until almost 11 AM. By this time the flight crew had been waiting for over an hour, and they had called management to get someone to open the door for them multiple times. Around 11:30, the gate screen had changed to a different flight. I ended up buying a last minute ticket with Southwest airline just to get to Chicago, because the next flight with American wasn’t until 7:19 pm that day. Now, earlier that morning my suitcase had been sent ahead of me to ORD. I went to baggage claim to ask them if I could have my suitcase forwarded to where I was staying. The representative at SDF baggage claim said they could and put the claim in for me. As I was going back through TSA, I got an email that the airline had found my suitcase, but the next step was to send it BACK to SDF. I called the airline support number again, and I made it clear that my suitcase needed to stay in Chicago and to not come back to SDF. The representative told me that they would hold my suitcase at ORD and that it wasn’t going to be forwarded anywhere. Once I got there, I found that they had loaded my suitcase onto a plane to send it back to SDF. Thankfully, I had gotten to the baggage claim counter in time for them to put in a request to bring my suitcase back up. My refund with the airline is processing already, but because of this entire experience and miscommunication at every turn of the way, I will not book with American Airlines in the future.

The plane was late and then sat on the runway for almost 45 minutes before taking off.

Crew professional. Easy bag drop off. On time. Good entertainment.

Everything was great. Boarding, early departure, early arrival, and deplaning were smooth. Smooth flight.

Per usual, flight status, staff courtesy and professionalism were excellent

The only thing is if Wi-Fi is available after you land and taxi to the gate. It takes forever to get to the gate, and having the Wi-Fi continue would be great to bide the time at least 5 minutes before you arrive at the entrance. That is my only comment; otherwise, everything was good.

Had to wait on pilot and crew to depart and had to wait to arrive at the gate because they only had 2 crews working. Delays, delays....Planes just keep getting smaller and tighter and they nickle and dime for everything. When will an airline actually wake up and make flying more enjoyable?

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

Information on your arrival and departure airports

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