ANC - CHI

$168 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 5/21. 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
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Everything you should know

Cheapest round-trip
$349
Overall average: $527
Alaska Airlines
Thu 6/18Wed 6/24
ANC - ORD • Non-stop
Cheapest non-stop
$401
Typical prices: $472-$601
Alaska Airlines
Thu 7/23Sun 7/26
ANC - ORD • Non-stop
Our travelers' advice
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
Alaska Airlines
Cheapest • from $349 (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 47% compared to booking last minute.
Insights
Insights
Insights
Insights
When to travel
October
Cheapest • 32% price drop
April
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

Thu, Jun 18 - Wed, Jun 24
Alaska Airlines Logo
11:24 pm - 8:40 am
ANC
-
ORD
6h 16mnonstop
Alaska Airlines Logo
6:53 pm - 9:47 am
ORD
-
ANC
17h 54m
1 stop
$349Alaska Airlines
Thu, Jun 11 - Sat, Jun 13
Alaska Airlines Logo
11:24 pm - 8:40 am
ANC
-
ORD
6h 16mnonstop
Alaska Airlines Logo
7:20 am - 10:09 am
ORD
-
ANC
29h 49m
1 stop
$352Alaska Airlines
Tue, Apr 14 - Sun, Apr 19
Delta Logo
6:00 am - 11:58 pm
ANC
-
ORD
14h 58m
1 stop
Delta Logo
6:25 am - 6:46 pm
ORD
-
ANC
15h 21m
1 stop
$359Delta
Wed, Mar 18 - Wed, Mar 25
Delta Logo
9:15 pm - 8:50 am
ANC
-
MDW
8h 35m
1 stop
Delta Logo
9:30 am - 6:51 pm
MDW
-
ANC
12h 21m
1 stop
$359Delta
Wed, Mar 18 - Mon, Mar 23
Delta Logo
1:34 am - 6:05 pm
ANC
-
ORD
13h 31m
2 stops
Delta Logo
7:25 am - 2:45 pm
ORD
-
ANC
10h 20m
1 stop
$364Delta
Tue, Apr 14 - Mon, Apr 20
Delta Logo
9:15 pm - 12:43 pm
ANC
-
MDW
12h 28m
2 stops
Delta Logo
9:31 am - 6:46 pm
MDW
-
ANC
12h 15m
1 stop
$364Delta
Wed, Feb 18 - Mon, Feb 23
Alaska Airlines Logo
3:50 pm - 12:01 pm
ANC
-
ORD
17h 11m
2 stops
Alaska Airlines Logo
2:07 pm - 5:35 pm
ORD
-
ANC
30h 28m
1 stop
$367Alaska Airlines
Thu, May 7 - Wed, May 13
Alaska Airlines Logo
12:22 pm - 6:40 am
ANC
-
ORD
15h 18m
1 stop
Alaska Airlines Logo
8:20 am - 12:08 pm
ORD
-
ANC
6h 48mnonstop
$368Alaska Airlines
Thu, Mar 19 - Mon, Mar 23
Delta Logo
3:40 pm - 9:10 am
ANC
-
ORD
14h 30m
2 stops
Delta Logo
3:59 pm - 12:29 am
ORD
-
ANC
11h 30m
2 stops
$369Delta
Sun, Mar 15 - Sun, Mar 22
Delta Logo
9:15 pm - 8:40 am
ANC
-
ORD
8h 25m
1 stop
Delta Logo
6:15 am - 6:51 pm
ORD
-
ANC
15h 36m
1 stop
$378Delta
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 $340 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, Wednesday 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 October, where tickets cost $318 (return) on average. On the other hand, the most expensive months are March and April, where the average cost of round-trip tickets is $671 and $592 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 $419 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 47% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 17 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$168
Best time to beat the crowds but there is an average 11% increase in price.
Most popular time to fly with an average 25% increase in price.
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 $168 for a one-way ticket and $349 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, and Hawaiian 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 $471 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 $439 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 $306 or less one-way and $518 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

United Airlines

United Airlines

Tuesday

United Airlines

United Airlines

Wednesday

United Airlines

United Airlines

Thursday

United Airlines

United Airlines

Friday

United Airlines

United Airlines

Saturday

United Airlines

United Airlines

Sunday

United Airlines

United Airlines

See more direct flights

Direct returns

Chicago to Anchorage

Monday

United Airlines

United Airlines

Tuesday

United Airlines

United Airlines

Wednesday

United Airlines

United Airlines

Thursday

United Airlines

United Airlines

Friday

United Airlines

United Airlines

Saturday

United Airlines

United Airlines

Sunday

United Airlines

United Airlines

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 11807 reviews
7.1Food
7.8Comfort
8.5Crew
7.0Entertainment
8.1Boarding
Airline reviews

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.

4.0 OkayJerry, Jan 2026
SAN - ORD
Read more Alaska Airlines reviews

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.

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.

Timing, quality of service, promptness and courtesy of the staff

It was last minute due to weather - considering - it was amazing! Good smiles, friendly staff and they were making sure we knew what was going on when and where.

delta last minute gave me a boarding pass for a different flight with no confirmation that they were changing it

The service from the flight attendants were of supreme quality. They greeted and treated everyone with a wide smile. This is totally absent nowadays. Kudos to them!!!!

Excellent flight and got us around tough weather. Only issue was seat TV did not work and crew tried to reboot.

Very large passenger too space from my own seat. Arm board couldn’t be lowered because of his size. It wads very uncomfortable trip, as the flight was full couldn’t move anywhere having back pain because of the position in which I was the entire flight.

was sitting in the jet bridge for 10 minutes in -20 degree weather waiting for my bag

Outdated equipment in disrepair, wifi inoperable. Broken seats, taped air vents, generally poor condition, the 717 showed its age and lack of upkeep.

My flight out of Baton Rouge to Atlanta was delayed by a half hour. This got us into Atlanta airport 30 minutes late. I ran through the airport to get to my connecting flight. As I approached the boarding gate, I saw the boarding door was still open and a passenger was being checked in. But when I got to the gate, the boarding agent told me they had already given away my seat and there were no empty seats on that flight. So I had to take a later flight. That has never happened to me before. Very frustrating.

Connection through Atlanta was difficult. Mechanical issue on plane caused a two hour delay. New gate was a mile away.

Yall need to integrate your system with Alaska more efficiently. They booted me off the first flight because of a discrepancy on your end.

The crew at Hawaiian Airlines was fantastic. Kind and hard working. The pilots were great with giving us all the updates to make sure we were informed.

Very good. Nice plane and we sat in economy plus - bigger seats, more room. They served a meal and snacks, and the meal was an apple stuffed pancake that was very good! The snack for us was a hummus sandwich - also very good. The flight attendants were helpful and nice. They have plenty of movies and shows to watch. My only negative -- they changed our flights around and did not adjust the layovers, so we ended up with a very long and unnecessary layover in Honolulu.

I liked the Starlink WiFi but didn't like how they said they were the only airline to offer a free meal and it turns out to be just a standalone sandwich and then charge for snacks to go with it. Rather have the free snacks like Southwest, but have the option to purchase a decent meal for a 5+ hour flight.

Flight scheduled to take off at 5.55pm but it did not take off until 7pm due to some food delivery delay.

Unfortunately, I was put into the middle seat in the first row of premium seating. Sounds nice right? No! that is the worst seat in the plane. I wish I was in economy rather than be in that seat! There is no seat back pocket, no tray table, no charger. Nothing! so unless you're row mates are willing to let you share their basic amenities any flyer should have, you are stuck. It was the worst experience ever! And the flight attendant forgot to take my drink order. I felt like the forgotten flyer.

Delayed and cancelled flights were hard and very stressful, both ways!

The crew was quite good, they came by often with drinks or to collect trash. But what wasn't nice was the flight was over weigh and several people had to be rebooked. I was questioned whether I should have a seat when I was getting to it. The in-flight entertainment kept buffering and interrupting. And the route took the airplane through high winds which caused us a longer flight

Wasn’t on the flight due to Alaska cancellation…also after all the rerouting, I was going to be on a later flight that left SFO at 7:47pm, which meant an almost 6 hour layover. That same Hawaiian flight was delayed for another 2hours.

I had to cancel the flight because with a 3 hour delay for 'unexpected maintenance' in getting to LAX, I couldn't connect to an overseas flight that I had booked on Scandinavian Air.

Seated dude next to me even though lots of empty rows. But main thing was we sat on the tarmac after landing for 30 minutes because of, in the words of the dude who sat next to me, “operational incompetence”. We got changing directions about where to pick up gate checked bags. Pilot and flight attendant were awesome though.

It was a pretty standard flight... until the almost hour and a half spent on the taxi way. I get that the weather has been poor but the delay had nothing to do with the weather and more to do with a plane with several issues tying up the gate. I get that that happens from time to time but this has been EVERY flight I've been on for the past 5 years and I fly 3 to 5 times a year. This isn't just United... it's American, it's Delta. It's an issue with the entire industry. I work for UPS and packages on a cargo plane get better service than people do these days. Anymore I HATE flying.

Perfect flight. Smooth flight. Arrived 20 minutes early at destination. Excellent service.

The flights were on time which was great give. It was holiday travel season and there’d been some weather issues. The only complaint and this is every time with United is the terrible seat design. The head rest is not built for comfort and having my neck bent forward for a cross country trip reminded me while I try not to take United flights as a rule.

Everything was absolutely wonderful from check in to baggage claim. Staff was very professional and sweet. Will definitely recommend United to family and friends.

They did the one thing that really matters - got to Chicago early.

The flight was on time. I generally don’t drink or eat on short flights and the seats were good and the flight attendants were friendly. That’s all I expect

It was nice to have gotten up upgraded to first class with a meal on a three hour flight

Very bad! They kept delaying my flight and wouldn’t do anything about it

Door to door, the crew and staff were amazing. It was a stressful travel day with delays, but they were focused on customers and doing what they could to get us to our destinations.

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

Information on your arrival and departure airports