HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Chicago

$188+ Cheap flights from Anchorage (ANC) to Chicago (CHI)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 5/5. Fares are subject to change and may not be available on all flights or dates of travel.
ANC — CHI
Apr 9 — Apr 161
Wed 4/9
Wed 4/16
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Anchorage to Chicago with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

Cheapflights Tip: The best prices from Anchorage to Chicago are usually found in November or October, booked 90 days in advance, depart on a Thursday or Tuesday and return on a Wednesday

Cheap flight deals from Anchorage to Chicago

Discover tips and strategies to find the most affordable flight options for your journey from Anchorage (ANC) to Chicago (CHI). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated April 4, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$375
(Mytrip)

One-way from

$188
(American Airlines)

Popular in

March

Cheapest in

November

Average price

$542

Good round-trip deal

$549 or less

Good one-way deal

$263 or less
Provider with most accurate pricing for Anchorage-Chicago (CHI) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Anchorage-Chicago (CHI) flights.
Search Deals
From Anchorage to Chicago (CHI)
Search Deals
One-way flight from Anchorage to Chicago (CHI)
Search Deals
Highest demand for flights based on searches. 13% potential increase in price ($80 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($13 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in April 2025
Search Deals
Price to beat on a round-trip flight from Anchorage to Chicago (CHI).
Search Deals
Price to beat on a one-way flight from Anchorage to Chicago (CHI).
Search Deals

Find flight deals from Anchorage to Chicago

Cheapest flights from Anchorage to Chicago
Explore the most affordable flight options available from Anchorage to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on April 4, 2025.

This Mytrip deal was found by Cheapflights users on 4/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/291:20 pmANC - ORD
1 stop20h 07mSun Country Air
Sun 6/18:05 pmORD - ANC
1 stop19h 13mSun Country Air
Deal found 4/2$375
This United Airlines deal was found by Cheapflights users on 4/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/28:50 pmANC - ORD
Nonstop6h 20mUnited Airlines
Mon 5/51:05 pmORD - ANC
Nonstop6h 39mUnited Airlines
Deal found 4/3$376
This Delta deal was found by Cheapflights users on 4/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/286:05 amANC - ORD
1 stop8h 20mDelta
Thu 6/56:20 pmORD - ANC
1 stop10h 12mDelta
Deal found 4/3$396
This Delta deal was found by Cheapflights users on 4/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/11:26 amANC - MDW
2 stops12h 53mDelta
Fri 5/91:08 pmMDW - ANC
2 stops15h 24mDelta
Deal found 4/3$406
This CheapTickets.de deal was found by Cheapflights users on 4/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapTickets.de is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/2411:00 amANC - ORD
1 stop9h 59mAlaska Airlines
Thu 5/13:44 pmORD - ANC
1 stop10h 48mAlaska Airlines
Deal found 4/3$418
This American Airlines deal was found by Cheapflights users on 4/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/269:48 pmANC - ORD
Nonstop6h 16mAmerican Airlines
Mon 6/95:07 pmORD - ANC
Nonstop6h 33mAmerican Airlines
Deal found 4/3$426
This Kiwi.com deal was found by Cheapflights users on 4/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/245:00 amANC - ORD
1 stop10h 01mHawaiian Airlines
Thu 5/17:19 pmORD - ANC
1 stop16h 17mHawaiian Airlines
Deal found 4/3$459
This Mytrip deal was found by Cheapflights users on 4/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/291:20 pmANC - ORD
3 stops31h 45mMultiple Airlines
Sun 6/18:05 pmORD - ANC
1 stop19h 13mMultiple Airlines
Deal found 4/2$465

Cheapflights Fare Finder

Customize your flight search to find flights from Anchorage to Chicago that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated April 4, 2025.
Use the filters below to find and compare flights from Anchorage to Chicago that are best for you.

Fly from

Anchorage

Fly to

Chicago

Route

Depart

Return

Price

AnchorageChicago

ANC - ORD

ANCORD

Anchorage

Thu 5/29

1:20 pm-12:27 pm

1 stop20h 07m

Chicago O'Hare Intl

Sun 6/1

8:05 pm-12:18 pm

1 stop19h 13m

$375

AnchorageChicago

ANC - ORD

ANCORD

Anchorage

Fri 5/2

8:50 pm-6:10 am

Nonstop6h 20m

Chicago O'Hare Intl

Mon 5/5

1:05 pm-4:44 pm

Nonstop6h 39m

$376

AnchorageChicago

ANC - ORD

ANCORD

Anchorage

Wed 5/28

12:55 am-1:30 pm

1 stop9h 35m

Chicago O'Hare Intl

Sun 6/1

2:25 pm-11:07 pm

1 stop11h 42m

$396

AnchorageChicago

ANC - MDW

ANCMDW

Anchorage

Thu 5/1

1:26 am-5:19 pm

2 stops12h 53m

Chicago Midway

Fri 5/9

1:08 pm-1:32 am

2 stops15h 24m

$406

AnchorageChicago

ANC - ORD

ANCORD

Anchorage

Thu 4/24

11:00 am-11:59 pm

1 stop9h 59m

Chicago O'Hare Intl

Thu 5/1

3:44 pm-11:32 pm

1 stop10h 48m

$418

AnchorageChicago

ANC - ORD

ANCORD

Anchorage

Mon 5/26

9:48 pm-7:04 am

Nonstop6h 16m

Chicago O'Hare Intl

Mon 6/9

5:07 pm-8:40 pm

Nonstop6h 33m

$426

AnchorageChicago

ANC - ORD

ANCORD

Anchorage

Thu 4/24

5:00 am-6:01 pm

1 stop10h 01m

Chicago O'Hare Intl

Thu 5/1

7:19 pm-8:36 am

1 stop16h 17m

$459

AnchorageChicago

ANC - ORD

ANCORD

Anchorage

Thu 5/29

1:20 pm-12:05 am

3 stops31h 45m

Chicago O'Hare Intl

Sun 6/1

8:05 pm-12:18 pm

1 stop19h 13m

$465

AnchorageChicago

ANC - ORD

ANCORD

Anchorage

Mon 5/5

9:48 pm-7:04 am

Nonstop6h 16m

$188

AnchorageChicago

ANC - ORD

ANCORD

Anchorage

Sun 4/27

1:26 am-1:19 pm

1 stop8h 53m

$197

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/3

Showing 1-10 of 15 results
1
2

Compare providers for flights from Anchorage to Chicago

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Anchorage to Chicago in April.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Anchorage-Chicago flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Anchorage-Chicago flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Anchorage-Chicago flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Anchorage-Chicago flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Anchorage-Chicago flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

The best insider tips for Anchorage to Chicago flights

Snippets provided in this section are AI-generated based on a summarization of Cheapflights-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.
Cheapflights partnered with top experts to bring you the best recommendations for your Anchorage to Chicago trip
Airports
ANC

Security wait times at ANC are generally short, thanks to advanced technologies. Arrive 2 hours early for domestic flights to ensure smooth check-in.

Read more about ANCby Taryn White
ORD

For a quick city connection from ORD, take the 'L' train from the airport to downtown Chicago, avoiding traffic delays.

Read more about ORDby Ramsey Qubein
Our travel experts
Ramsey Qubein

Ramsey Qubein

Expert on ORD

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
Taryn White

Taryn White

Expert on ANC

Taryn White

Taryn White

Taryn White is a freelance travel writer, digital creator, and travel advisor who has visited nearly 100 countries and all 50 states. She’s familiar with many airports and enjoys beach hopping, boutique hotels, spa experiences, and exploring local culture. Her work has appeared in Travel + Leisure, Condé Nast Traveler, National Geographic, Smithsonian Magazine, AFAR, and more.

Read more

Best time to book a flight from Anchorage to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from Anchorage with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

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

How far ahead should I book a flight from Anchorage to Chicago?

Use this chart to determine the optimal time to book a round-trip flight from Anchorage to Chicago. Price data was last updated on March 28, 2025.

Booking 90 days in advance of your planned departure date is, on average, the best time to get cheap flights from Anchorage to Chicago. The general trend is that the closer you book to the departure date, the more expensive your flight will be.

What is the cheapest month to book a flight from Anchorage to Chicago?

Currently, August is the cheapest month in which you can book a flight from Anchorage to Chicago (average of $245). Flying from Anchorage to Chicago in March is currently the most expensive (average of $321). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from ANC to CHI?

Find hourly flight availability from Anchorage to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated April 4, 2025.

When flying from Anchorage to Chicago, the time of day you fly usually plays a role in the price. Save by searching for a flight at noon, which can drop the price by up to 57% versus a flight in the afternoon.

Rainfall in Chicago by month

Plan your trip to Chicago by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Chicago ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago when rainfall is around 1.7 in.

Temperature in Chicago by month

Plan your trip to Chicago by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Chicago, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

Reviews of airlines servicing Chicago

Get insights into the airlines that provide service to Chicago. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Chicago. Reviews last updated April 4, 2025.
To help decide which airline to fly from Anchorage to Chicago, see what other customers have to say about Alaska Airlines, Delta and Hawaiian Airlines. In addition to providing an overall rating, users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Alaska Airlines
8.0
Very good
9,836 reviews

Comfort

7.9

Boarding

8.2

Food

7.1

Entertainment

7.1

Crew

8.5

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them
Alaska Airlines
8.0
Very good
9,836 reviews
Alaska Airlines
8.0
Very good
9,836 reviews

Comfort

7.9

Boarding

8.2

Food

7.1

Entertainment

7.1

Crew

8.5

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them
Delta
8.0
Very good
7,897 reviews
Alaska Airlines
8.0
Very good
9,836 reviews

Comfort

7.9

Boarding

8.2

Food

7.1

Entertainment

7.1

Crew

8.5

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them
Hawaiian Airlines
7.9
Good
2,347 reviews
Alaska Airlines
8.0
Very good
9,836 reviews

Comfort

7.9

Boarding

8.2

Food

7.1

Entertainment

7.1

Crew

8.5

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them
United Airlines
7.4
Good
8,618 reviews
Alaska Airlines
8.0
Very good
9,836 reviews

Comfort

7.9

Boarding

8.2

Food

7.1

Entertainment

7.1

Crew

8.5

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them
American Airlines
7.2
Good
10,000 reviews
Alaska Airlines
8.0
Very good
9,836 reviews

Comfort

7.9

Boarding

8.2

Food

7.1

Entertainment

7.1

Crew

8.5

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them

Related info for your journey

Find useful and relevant information for your journey from Anchorage to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly from for flights from Anchorage to Chicago?

    Located just 4.4 mi from the city center, Anchorage is the airport most travelers will use when flying to Chicago from Anchorage. Booking flights from Anchorage (ANC) to Chicago should be relatively easy as there is 1 daily outbound flight to Chicago from 4 different airlines.

  • What are the cheapest airlines flying from Anchorage to Chicago round-trip?

    Flying on Sun Country Air is currently your cheapest option to Chicago, with prices starting at $375. Additional round-trip tickets that might be worth considering are offered by United Airlines and Delta, with the lowest prices starting at $376 and $396, respectively. These flights start at 26% lower than the current average price 3 months from now.

  • What are the cheapest airlines to fly from Anchorage to Chicago one-way?

    The cheapest airlines for a one-way flight from Anchorage to Chicago are American Airlines ($188), Alaska Airlines ($197), and Delta ($203).

  • What are the most reliable airlines from Anchorage to Chicago?

    Looking for the most reliable airlines to get you to your destination on time? Our data shows these are most likely to get you from Anchorage to Chicago on time: Qatar Airways (100%), Alaska Airlines (100%), Air Canada (100%).

  • What are the cheapest flights from Anchorage to Chicago?

    Looking at all options, your cheapest flight can be booked for $199. While the most popular route (Anchorage - Chicago O'Hare Intl) can be booked for $376 on average our data indicates $1,164 when flying from Anchorage to Chicago.

  • Can I find deals for flights from Anchorage to Chicago that include hotel bookings?

    Yes. In addition to deals on Anchorage to Chicago flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Anchorage to Chicago?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Anchorage to Chicago.

  • Can I find deals for business class flights from Anchorage to Chicago?

    Yes. Cheapflights offers flight deals from Anchorage to Chicago by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Anchorage to Chicago?

    Currently, August is the cheapest month in which you can book a flight from Anchorage to Chicago (average of $245). Flying from Anchorage to Chicago in March is currently the most expensive (average of $321). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Traveling to a place near Anchorage?

Book flights to Anchorage if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Benton Harbor
Porter
Lansing
Valparaiso
Chesterton

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Top 4 airlines flying from Anchorage to Chicago

Discover the top 4 airlines that operate flights from Anchorage to Chicago. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated April 4, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$259Average$416FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$338Average$467FlexibilityNo cancel feeOn-time71%
Alaska AirlinesCheapest$339Average$487FlexibilityNo cancel feeOn-time75%
United AirlinesCheapest$345Average$486FlexibilityNo cancel feeOn-time69%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.