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$168+ 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 6/10. Fares are subject to change and may not be available on all flights or dates of travel.
ANC — CHI
Jan 11 — Jan 181
Sun 1/11
Sun 1/18
1 adult, Economy
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Cheap 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 December 12, 2025.

This Alaska Airlines deal was found by Cheapflights users on 12/10. 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 12/1210:20 amANC - ORD
1 stop10h 39mAlaska Airlines
Sat 12/139:40 amORD - ANC
2 stops17h 04mAlaska Airlines
Deal found 12/10$716
This United Airlines deal was found by Cheapflights users on 12/10. 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.
Thu 12/259:00 pmANC - ORD
Nonstop6h 24mUnited Airlines
Mon 12/293:58 pmORD - ANC
Nonstop6h 47mUnited Airlines
Deal found 12/10$770
This United Airlines deal was found by Cheapflights users on 12/11. 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.
Mon 12/229:00 pmANC - ORD
Nonstop6h 24mUnited Airlines
Mon 12/293:58 pmORD - ANC
Nonstop6h 47mUnited Airlines
Deal found 12/11$793
This United Airlines deal was found by Cheapflights users on 12/11. 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.
Wed 12/249:00 pmANC - ORD
Nonstop6h 24mUnited Airlines
Sun 12/285:50 pmORD - ANC
1 stop9h 35mUnited Airlines
Deal found 12/11$796
This Delta deal was found by Cheapflights users on 12/9. 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.
Sun 12/1412:30 amANC - ORD
1 stop13h 45mDelta
Fri 12/198:50 amORD - ANC
1 stop13h 14mDelta
Deal found 12/9$812
This Delta deal was found by Cheapflights users on 12/9. 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.
Mon 12/156:05 amANC - MDW
1 stop9h 13mDelta
Fri 12/199:59 amMDW - ANC
1 stop12h 05mDelta
Deal found 12/9$812
This United Airlines deal was found by Cheapflights users on 12/9. 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.
Mon 12/1511:59 pmANC - ORD
1 stop10h 16mUnited Airlines
Fri 12/193:58 pmORD - ANC
Nonstop6h 47mUnited Airlines
Deal found 12/9$831
This Delta deal was found by Cheapflights users on 12/11. 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 12/126:05 amANC - MDW
1 stop9h 13mDelta
Sun 12/286:00 amMDW - ANC
1 stop15h 57mDelta
Deal found 12/11$887
This Delta deal was found by Cheapflights users on 12/11. 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.
Tue 12/238:15 pmANC - MDW
1 stop15h 29mDelta
Sun 12/286:00 amMDW - ANC
1 stop15h 57mDelta
Deal found 12/11$936
This Delta deal was found by Cheapflights users on 12/11. 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 12/241:44 pmANC - MDW
2 stops16h 05mDelta
Sun 12/286:00 amMDW - ANC
1 stop15h 57mDelta
Deal found 12/11$941
This Delta deal was found by Cheapflights users on 12/11. 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 12/263:40 pmANC - MDW
2 stops14h 09mDelta
Sun 12/286:00 amMDW - ANC
1 stop15h 57mDelta
Deal found 12/11$965

Find 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 December 12, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$355
(Kiwi.com)

One-way from

$168
(Kiwi.com)

Popular in

March

Cheapest in

October

Average price

$408

Good round-trip deal

$670 or less

Good one-way deal

$313 or less
Provider with most accurate pricing for Anchorage-Chicago (CHI) flight deals.
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Provider most trusted by Cheapflights users for Anchorage-Chicago (CHI) flights.
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From Anchorage to Chicago (CHI)
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One-way flight from Anchorage to Chicago (CHI)
Search Deals
Highest demand for flights based on searches. 23% potential increase in price ($158 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 5% potential price decrease ($28 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 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

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 December 12, 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

Mon 2/2

10:05 am-11:50 pm

1 stop10h 45m

Chicago O'Hare Intl

Thu 2/5

2:06 pm-8:58 pm

1 stop9h 52m

$355

AnchorageChicago

ANC - ORD

ANCORD

Anchorage

Sun 1/25

12:49 am-1:10 pm

1 stop9h 21m

Chicago O'Hare Intl

Sat 1/31

3:35 pm-10:52 pm

1 stop10h 17m

$357

AnchorageChicago

ANC - ORD

ANCORD

Anchorage

Sat 1/10

6:10 am-5:54 pm

1 stop8h 44m

Chicago O'Hare Intl

Sat 1/17

12:30 pm-6:56 pm

1 stop9h 26m

$358

AnchorageChicago

ANC - ORD

ANCORD

Anchorage

Fri 1/9

5:55 am-11:53 pm

1 stop14h 58m

Chicago O'Hare Intl

Tue 1/13

6:15 am-6:56 pm

1 stop15h 41m

$358

AnchorageChicago

ANC - ORD

ANCORD

Anchorage

Tue 1/13

6:10 am-9:43 pm

1 stop12h 33m

Chicago O'Hare Intl

Sun 2/8

6:15 am-6:56 pm

1 stop15h 41m

$358

AnchorageChicago

ANC - ORD

ANCORD

Anchorage

Sat 2/21

5:15 am-11:56 pm

1 stop15h 41m

Chicago O'Hare Intl

Wed 2/25

7:00 am-11:04 pm

1 stop19h 04m

$358

AnchorageChicago

ANC - ORD

ANCORD

Anchorage

Thu 5/7

11:00 am-11:58 pm

1 stop9h 58m

Chicago O'Hare Intl

Wed 5/13

7:51 pm-2:31 am

1 stop9h 40m

$358

AnchorageChicago

ANC - ORD

ANCORD

Anchorage

Wed 1/14

9:15 pm-8:40 am

1 stop8h 25m

Chicago O'Hare Intl

Sat 1/17

8:00 am-7:01 pm

1 stop14h 01m

$358

AnchorageChicago

ANC - ORD

ANCORD

Anchorage

Fri 1/9

9:15 pm-8:40 am

1 stop8h 25m

Chicago O'Hare Intl

Fri 1/16

6:15 am-6:56 pm

1 stop15h 41m

$358

AnchorageChicago

ANC - ORD

ANCORD

Anchorage

Mon 1/19

1:20 am-1:22 pm

1 stop9h 02m

Chicago O'Hare Intl

Tue 1/27

6:15 am-6:56 pm

1 stop15h 41m

$358

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/11

Showing 1-10 of 31 results
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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 December.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star
eDreamsPrice 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 eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Anchorage-Chicago flight deals on Cheapflights vs. eDreams >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 eDreams the most. eDreams 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.

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

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

Currently, May is the cheapest month in which you can book a flight from Anchorage to Chicago (average of $187). Flying from Anchorage to Chicago in January is currently the most expensive (average of $463). 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 December 12, 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 afternoon, which can drop the price by up to 48% versus a flight in the morning.

How much does it cost to fly round-trip from Anchorage to Chicago?

The best insider tips for Anchorage to Chicago flights

AI-powered summary based on content written by travel experts. AI can make mistakes.
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

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 December 12, 2025.
Get a feel of what it's like to fly with Alaska Airlines, Delta, and Hawaiian 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
11,431 reviews

Entertainment

7.0

Crew

8.5

Boarding

8.1

Overall

8.0

Food

7.1

Comfort

7.8

Reviews

1 / 20
2.0
Mediocre

Art,Dec 2025

SAN - OGG

It was a five hour flight and my seat did not recline. I have had three back surgeries and I’m solid bone for my L3 vertebrae all the way to my tailbone. My body has never hurt so much. There was no TV on this flight and only a small can of soda was free.
Alaska Airlines
8.0
Very good
11,431 reviews
Alaska Airlines
8.0
Very good
11,431 reviews

Entertainment

7.0

Crew

8.5

Boarding

8.1

Overall

8.0

Food

7.1

Comfort

7.8

Reviews

1 / 20
2.0
Mediocre

Art,Dec 2025

SAN - OGG

It was a five hour flight and my seat did not recline. I have had three back surgeries and I’m solid bone for my L3 vertebrae all the way to my tailbone. My body has never hurt so much. There was no TV on this flight and only a small can of soda was free.
Delta
7.9
Good
8,009 reviews
Alaska Airlines
8.0
Very good
11,431 reviews

Entertainment

7.0

Crew

8.5

Boarding

8.1

Overall

8.0

Food

7.1

Comfort

7.8

Reviews

1 / 20
2.0
Mediocre

Art,Dec 2025

SAN - OGG

It was a five hour flight and my seat did not recline. I have had three back surgeries and I’m solid bone for my L3 vertebrae all the way to my tailbone. My body has never hurt so much. There was no TV on this flight and only a small can of soda was free.
Hawaiian Airlines
7.8
Good
2,818 reviews
Alaska Airlines
8.0
Very good
11,431 reviews

Entertainment

7.0

Crew

8.5

Boarding

8.1

Overall

8.0

Food

7.1

Comfort

7.8

Reviews

1 / 20
2.0
Mediocre

Art,Dec 2025

SAN - OGG

It was a five hour flight and my seat did not recline. I have had three back surgeries and I’m solid bone for my L3 vertebrae all the way to my tailbone. My body has never hurt so much. There was no TV on this flight and only a small can of soda was free.
United Airlines
7.4
Good
9,095 reviews
Alaska Airlines
8.0
Very good
11,431 reviews

Entertainment

7.0

Crew

8.5

Boarding

8.1

Overall

8.0

Food

7.1

Comfort

7.8

Reviews

1 / 20
2.0
Mediocre

Art,Dec 2025

SAN - OGG

It was a five hour flight and my seat did not recline. I have had three back surgeries and I’m solid bone for my L3 vertebrae all the way to my tailbone. My body has never hurt so much. There was no TV on this flight and only a small can of soda was free.

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 0 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 8h 44m. 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 $158. Additional round-trip tickets that might be worth considering are offered by Delta and United Airlines, with the lowest prices starting at $187 and $254, respectively. These flights start at 69% 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 Hawaiian Airlines ($156), United Airlines ($158), and Delta ($178).

  • 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 (86%), Korean Air (83%), Alaska Airlines (76%).

  • What are the cheapest flights from Anchorage to Chicago?

    Looking at all options, your cheapest flight can be booked for $203. While the most popular route (Anchorage - Chicago O'Hare Intl) can be booked for $357 on average, our data indicates $1,106 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, May is the cheapest month in which you can book a flight from Anchorage to Chicago (average of $187). Flying from Anchorage to Chicago in January is currently the most expensive (average of $463). 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
Lansing
Merrillville
Hammond
Porter
Benton Harbor

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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 December 12, 2025.
AirlineCheapestAverageFlexibilityOn-time
Hawaiian AirlinesCheapest$187Average$461FlexibilityNo cancel feeOn-time85%
DeltaCheapest$259Average$408FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$314Average$484FlexibilityNo cancel feeOn-time69%
Alaska AirlinesCheapest$318Average$501FlexibilityNo cancel feeOn-time75%
American AirlinesCheapest$338Average$513FlexibilityNo cancel feeOn-time71%

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