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$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 3/23. Fares are subject to change and may not be available on all flights or dates of travel.
ANC — CHI
Jan 26 — Feb 21
Sun 1/26
Sun 2/2
1 adult, Economy
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The best prices from Anchorage to Chicago are usually found in November or May, booked 90 days in advance, depart on a Tuesday or Friday and return on a Tuesday

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 January 21, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$389
(Alaska Airlines)

One-way from

$188
(Alaska Airlines)

Popular in

February

Cheapest in

November

Average price

$528
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)
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High demand for flights, 16% potential price rise
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Best time to find cheap flights, 2% potential price drop
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Average for round-trip flights in January 2025
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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 January 21, 2025.

This Alaska Airlines deal was found by Cheapflights users on 1/20. 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.
Thu 4/36:00 amANC - ORD
1 stop20h 40mAlaska Airlines
Mon 4/79:00 amORD - ANC
Nonstop6h 55mAlaska Airlines
Deal found 1/20$389
This Delta deal was found by Cheapflights users on 1/20. 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 2/215:55 amANC - ORD
1 stop15h 01mDelta
Sun 3/27:00 amORD - ANC
1 stop10h 58mDelta
Deal found 1/20$396
This Delta deal was found by Cheapflights users on 1/21. 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 4/2212:40 amANC - MDW
2 stops13h 23mDelta
Wed 4/301:16 pmMDW - ANC
1 stop9h 17mDelta
Deal found 1/21$401
This United Airlines deal was found by Cheapflights users on 1/20. 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.
Sun 5/411:44 pmANC - ORD
1 stop10h 31mUnited Airlines
Fri 5/91:05 pmORD - ANC
Nonstop6h 39mUnited Airlines
Deal found 1/20$407
This American Airlines deal was found by Cheapflights users on 1/20. 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.
Sat 5/31:31 amANC - ORD
1 stop12h 53mAmerican Airlines
Fri 5/94:50 pmORD - ANC
Nonstop6h 28mAmerican Airlines
Deal found 1/20$571
This Kiwi.com deal was found by Cheapflights users on 1/20. 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.
Fri 2/217:18 pmANC - ORD
1 stop16h 51mMultiple Airlines
Sun 3/24:05 pmORD - ANC
1 stop11h 24mMultiple Airlines
Deal found 1/20$578

Find flights from Anchorage to Chicago within your budget

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 January 21, 2025.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

AnchorageChicago

ANC - ORD

ANCORD

Anchorage

Thu 4/3

6:00 am-5:40 am

1 stop20h 40m

Chicago O'Hare Intl

Mon 4/7

9:00 am-12:55 pm

Nonstop6h 55m

$389

AnchorageChicago

ANC - ORD

ANCORD

Anchorage

Fri 2/21

5:55 am-11:56 pm

1 stop15h 01m

Chicago O'Hare Intl

Sun 3/2

7:00 am-2:58 pm

1 stop10h 58m

$396

AnchorageChicago

ANC - MDW

ANCMDW

Anchorage

Tue 4/22

12:40 am-5:03 pm

2 stops13h 23m

Chicago Midway

Wed 4/30

1:16 pm-7:33 pm

1 stop9h 17m

$401

AnchorageChicago

ANC - ORD

ANCORD

Anchorage

Thu 4/3

8:30 pm-5:50 am

Nonstop6h 20m

Chicago O'Hare Intl

Mon 4/7

3:40 pm-7:21 pm

Nonstop6h 41m

$456

AnchorageChicago

ANC - ORD

ANCORD

Anchorage

Fri 2/21

7:18 pm-3:09 pm

1 stop16h 51m

Chicago O'Hare Intl

Sun 3/2

4:05 pm-12:29 am

1 stop11h 24m

$578

AnchorageChicago

ANC - ORD

ANCORD

Anchorage

Sun 3/23

10:00 pm-7:40 am

Nonstop6h 40m

$188

AnchorageChicago

ANC - ORD

ANCORD

Anchorage

Sun 2/9

1:20 am-1:30 pm

1 stop9h 10m

$197

AnchorageChicago

ANC - MDW

ANCMDW

Anchorage

Sun 4/27

12:40 am-5:03 pm

2 stops13h 23m

$203

AnchorageChicago

ANC - ORD

ANCORD

Anchorage

Fri 4/11

8:30 pm-5:50 am

Nonstop6h 20m

$228

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/20

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 January.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
CheapfaremartPrice Accuracy-Trust Score*1 star

*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.

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.

Travel insights for flights from Anchorage to Chicago

Get recent, data-driven insights about flights from Anchorage to Chicago including ideal travel times, pricing trends, and more.

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 January 17, 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 $320). 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 January 21, 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 42% versus a flight in the morning.

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 January 21, 2025.
To help decide which airline to fly from Anchorage to Chicago, see what other customers have to say about Alaska Airlines and Delta. 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
9,706 reviews

Boarding

8.2

Crew

8.5

Comfort

7.9

Overall

8.0

Entertainment

7.1

Food

7.1

Reviews

1 / 10

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
9,706 reviews
Alaska Airlines
8.0
Very good
9,706 reviews

Boarding

8.2

Crew

8.5

Comfort

7.9

Overall

8.0

Entertainment

7.1

Food

7.1

Reviews

1 / 10

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
8,521 reviews
Alaska Airlines
8.0
Very good
9,706 reviews

Boarding

8.2

Crew

8.5

Comfort

7.9

Overall

8.0

Entertainment

7.1

Food

7.1

Reviews

1 / 10

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
8,984 reviews
Alaska Airlines
8.0
Very good
9,706 reviews

Boarding

8.2

Crew

8.5

Comfort

7.9

Overall

8.0

Entertainment

7.1

Food

7.1

Reviews

1 / 10

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 are 0 daily outbound flights to Chicago from 4 different airlines.

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

    Flying on Alaska Airlines is currently your cheapest option to Chicago, with prices starting at $389. Additional round-trip tickets that might be worth considering are offered by Delta and United Airlines, with the lowest prices starting at $396 and $456, respectively. These flights start at 21% 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 Alaska Airlines ($188), Delta ($197), and United Airlines ($228).

  • 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: Air Canada (82%), Korean Air (62%), United Airlines (61%).

  • What are the cheapest flights from Anchorage to Chicago?

    Looking at all options, your cheapest flight can be booked for $212. While the most popular route (Anchorage - Chicago O'Hare Intl) can be booked for $401 on average our data indicates $1,030 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 $320). 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

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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 January 21, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$195Average$460FlexibilityNo cancel feeOn-time71%
DeltaCheapest$293Average$470FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$335Average$516FlexibilityNo cancel feeOn-time69%
Alaska AirlinesCheapest$339Average$491FlexibilityNo cancel feeOn-time75%
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