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$159+ 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 10/16. Fares are subject to change and may not be available on all flights or dates of travel.
ANC — CHI
Aug 23 — Aug 301
Sat 8/23
Sat 8/30
1 adult, Economy
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Cheapflights Tip: The best prices from Anchorage to Chicago are usually found in November or September, booked 90 days in advance, depart on a Tuesday or Sunday 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 August 18, 2025.

Round-trip from

$318
(Alaska Airlines)

One-way from

$159
(Hawaiian Airlines)

Popular in

March

Cheapest in

November

Average price

$424

Good round-trip deal

$484 or less

Good one-way deal

$319 or less
From Anchorage to Chicago (CHI)
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One-way flight from Anchorage to Chicago (CHI)
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Highest demand for flights based on searches. 16% potential increase in price ($100 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($16 potential savings vs. average RT price).
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Average for round-trip flights in August 2025
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Price to beat on a round-trip flight from Anchorage to Chicago (CHI).
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Price to beat on a one-way flight from Anchorage to Chicago (CHI).
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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 August 18, 2025.

This Hawaiian Airlines deal was found by Cheapflights users on 8/18. 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 Hawaiian Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/211:25 pmANC - ORD
Nonstop6h 15mHawaiian Airlines
Sat 10/118:10 amORD - ANC
Nonstop6h 58mHawaiian Airlines
Deal found 8/18$318
This American Airlines deal was found by Cheapflights users on 8/16. 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.
Fri 9/199:53 pmANC - ORD
Nonstop6h 24mAmerican Airlines
Sun 9/215:01 pmORD - ANC
Nonstop6h 47mAmerican Airlines
Deal found 8/16$319
This CheapTickets deal was found by Cheapflights users on 8/16. 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/308:41 amANC - ORD
1 stop10h 26mMultiple Airlines
Tue 10/76:00 amORD - ANC
1 stop11h 15mMultiple Airlines
Deal found 8/16$322
This Hawaiian Airlines deal was found by Cheapflights users on 8/18. 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 Hawaiian Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/211:25 pmANC - ORD
Nonstop6h 15mHawaiian Airlines
Sat 10/47:00 amORD - ANC
1 stop9h 22mHawaiian Airlines
Deal found 8/18$328
This TeaFlight deal was found by Cheapflights users on 8/16. 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 TeaFlight is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/308:41 amANC - ORD
1 stop10h 26mAlaska Airlines
Tue 10/78:20 amORD - ANC
2 stops13h 26mAlaska Airlines
Deal found 8/16$336
This American Airlines deal was found by Cheapflights users on 8/17. 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.
Thu 10/29:53 pmANC - ORD
Nonstop6h 24mAmerican Airlines
Sat 10/1110:29 amORD - ANC
1 stop11h 15mAmerican Airlines
Deal found 8/17$337
This Delta deal was found by Cheapflights users on 8/18. 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 10/211:15 amANC - ORD
1 stop9h 40mDelta
Sat 10/45:15 pmORD - ANC
1 stop11h 21mDelta
Deal found 8/18$338
This Delta deal was found by Cheapflights users on 8/17. 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.
Fri 9/2610:00 pmANC - MDW
1 stop7h 53mDelta
Sat 10/411:00 amMDW - ANC
1 stop10h 56mDelta
Deal found 8/17$338
This Trip.com deal was found by Cheapflights users on 8/17. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/1410:00 amANC - ORD
1 stop10h 59mHawaiian Airlines
Fri 10/179:10 amORD - ANC
Nonstop6h 58mHawaiian Airlines
Deal found 8/17$340
This Alaska Airlines deal was found by Cheapflights users on 8/17. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/224:40 amANC - ORD
1 stop21h 21mAlaska Airlines
Wed 10/292:05 pmORD - ANC
1 stop9h 57mAlaska Airlines
Deal found 8/17$341
This Alaska Airlines deal was found by Cheapflights users on 8/16. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/1011:11 pmANC - ORD
Nonstop6h 29mAlaska Airlines
Sat 10/112:04 pmORD - ANC
1 stop9h 44mAlaska Airlines
Deal found 8/16$342
This Delta deal was found by Cheapflights users on 8/16. 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.
Sat 9/205:45 pmANC - MDW
2 stops11h 55mDelta
Sat 9/279:20 amMDW - ANC
2 stops13h 54mDelta
Deal found 8/16$348

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 August 18, 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

Fri 9/26

11:25 pm-8:40 am

Nonstop6h 15m

Chicago O'Hare Intl

Sat 10/4

8:10 am-12:08 pm

Nonstop6h 58m

$318

AnchorageChicago

ANC - ORD

ANCORD

Anchorage

Thu 9/18

11:59 pm-9:08 am

Nonstop6h 09m

Chicago O'Hare Intl

Sun 9/21

4:00 pm-7:47 pm

Nonstop6h 47m

$318

AnchorageChicago

ANC - ORD

ANCORD

Anchorage

Thu 10/2

11:25 pm-8:40 am

Nonstop6h 15m

Chicago O'Hare Intl

Sat 10/4

8:10 am-12:08 pm

Nonstop6h 58m

$318

AnchorageChicago

ANC - ORD

ANCORD

Anchorage

Fri 10/10

11:11 pm-8:40 am

Nonstop6h 29m

Chicago O'Hare Intl

Sat 10/18

8:10 am-12:08 pm

Nonstop6h 58m

$318

AnchorageChicago

ANC - ORD

ANCORD

Anchorage

Fri 10/10

11:11 pm-8:40 am

Nonstop6h 29m

Chicago O'Hare Intl

Sat 10/18

8:10 am-12:08 pm

Nonstop6h 58m

$318

AnchorageChicago

ANC - ORD

ANCORD

Anchorage

Thu 10/2

11:25 pm-8:40 am

Nonstop6h 15m

Chicago O'Hare Intl

Sat 10/11

8:10 am-12:08 pm

Nonstop6h 58m

$318

AnchorageChicago

ANC - ORD

ANCORD

Anchorage

Thu 10/2

11:25 pm-8:40 am

Nonstop6h 15m

Chicago O'Hare Intl

Sat 10/11

8:10 am-12:08 pm

Nonstop6h 58m

$318

AnchorageChicago

ANC - ORD

ANCORD

Anchorage

Fri 9/19

9:53 pm-7:17 am

Nonstop6h 24m

Chicago O'Hare Intl

Sun 9/21

5:01 pm-8:48 pm

Nonstop6h 47m

$319

AnchorageChicago

ANC - MDW

ANCMDW

Anchorage

Mon 10/6

6:05 am-5:43 pm

1 stop8h 38m

Chicago Midway

Sat 10/11

7:10 pm-12:51 am

1 stop8h 41m

$338

AnchorageChicago

ANC - MDW

ANCMDW

Anchorage

Fri 9/26

10:00 pm-8:53 am

1 stop7h 53m

Chicago Midway

Sat 10/4

1:43 pm-6:53 pm

1 stop8h 10m

$338

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/16

Showing 1-10 of 24 results
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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. Arrive 2 hours early for domestic flights to ensure smooth check-in and screening.

Read more about ANCby Taryn White
ORD

For a quick city transfer, take the 'L' train from ORD to downtown Chicago, avoiding potential 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 August 8, 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 August 18, 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 in the morning, which can drop the price by up to 56% versus a flight at noon.

Weekly flight availability from Anchorage to Chicago

Explore weekly flight availability from Anchorage to Chicago. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated August 18, 2025.

The most flights from ANC to CHI are scheduled on a Monday (12 on average). You will have fewer flight options on Wednesday, which is when the least amount of flights are scheduled (2 on average).

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 August 18, 2025.
Get a feel of what it's like to fly with Alaska Airlines, Delta, and United Airlines from Anchorage to Chicago by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Alaska Airlines
8.0
Very good
10,000 reviews

Comfort

7.8

Entertainment

7.0

Overall

8.0

Boarding

8.1

Crew

8.5

Food

7.1

Reviews

1 / 20
10.0
Excellent

Anonymous,Aug 2025

MFR - SEA

Great smooth flight. Was hour and half late though. Don't know why
Alaska Airlines
8.0
Very good
10,000 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Comfort

7.8

Entertainment

7.0

Overall

8.0

Boarding

8.1

Crew

8.5

Food

7.1

Reviews

1 / 20
10.0
Excellent

Anonymous,Aug 2025

MFR - SEA

Great smooth flight. Was hour and half late though. Don't know why
Delta
8.0
Very good
7,981 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Comfort

7.8

Entertainment

7.0

Overall

8.0

Boarding

8.1

Crew

8.5

Food

7.1

Reviews

1 / 20
10.0
Excellent

Anonymous,Aug 2025

MFR - SEA

Great smooth flight. Was hour and half late though. Don't know why
United Airlines
7.4
Good
8,925 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Comfort

7.8

Entertainment

7.0

Overall

8.0

Boarding

8.1

Crew

8.5

Food

7.1

Reviews

1 / 20
10.0
Excellent

Anonymous,Aug 2025

MFR - SEA

Great smooth flight. Was hour and half late though. Don't know why

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 are 8 daily outbound flights to Chicago from 5 different airlines.

  • How long is the flight from Anchorage to Chicago?

    Departing from Anchorage to Chicago will take you 6h 09m. There are 2837 mi between Anchorage and Chicago. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

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

    Flying on Hawaiian Airlines is currently your cheapest option to Chicago, with prices starting at $187. Additional round-trip tickets that might be worth considering are offered by Alaska Airlines and Delta, with the lowest prices starting at $337 and $337, respectively. These flights start at 63% 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 ($159), Alaska Airlines ($159), and Delta ($168).

  • 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: United Airlines (79%), Air Canada (79%), Atlas Air (78%).

  • What are the cheapest flights from Anchorage to Chicago?

    Looking at all options, your cheapest flight can be booked for $198. While the most popular route (Anchorage - Chicago O'Hare Intl) can be booked for $310 on average our data indicates $880 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 Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
Lansing
Hammond
Benton Harbor
Porter
Chesterton

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Top 5 airlines flying from Anchorage to Chicago

Discover the top 5 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 August 18, 2025.
AirlineCheapestAverageFlexibilityOn-time
Hawaiian AirlinesCheapest$187Average$461FlexibilityNo cancel feeOn-time85%
DeltaCheapest$337Average$423FlexibilityNo cancel feeOn-timeN/A
Alaska AirlinesCheapest$337Average$502FlexibilityNo cancel feeOn-time75%
American AirlinesCheapest$338Average$574FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$345Average$499FlexibilityNo cancel feeOn-time69%

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