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$169+ 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 11/15. Fares are subject to change and may not be available on all flights or dates of travel.
ANC — CHI
nov. 27 — dic. 41
jue. 11/27
jue. 12/4
1 adult, Economy
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Cheapflights Tip: The best prices from Anchorage to Chicago are usually found in November or September, booked 51 days in advance, depart on a Tuesday or Wednesday and return on a Wednesday

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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 octubre 28, 2025.

This United Airlines deal was found by Cheapflights users on 10/27. 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.
dom. 11/239:07 pmANC - ORD
Nonstop6h 02mUnited Airlines
vie. 11/284:05 pmORD - ANC
Nonstop6h 54mUnited Airlines
Deal found 10/27$338
This Delta deal was found by Cheapflights users on 10/28. 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.
lun. 11/1712:30 amANC - ORD
1 stop13h 48mDelta
vie. 11/287:47 amORD - ANC
1 stop11h 55mDelta
Deal found 10/28$358
This Delta deal was found by Cheapflights users on 10/27. 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.
vie. 12/129:45 pmANC - MDW
1 stop12h 25mDelta
dom. 12/2811:48 amMDW - ANC
1 stop10h 01mDelta
Deal found 10/27$358
This Cheapflightsfares deal was found by Cheapflights users on 10/26. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 12/85:05 amANC - ORD
1 stop8h 50mAlaska Airlines
jue. 12/112:05 pmORD - ANC
2 stops11h 39mAlaska Airlines
Deal found 10/26$359
This Delta deal was found by Cheapflights users on 10/28. 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.
vie. 12/56:05 amANC - MDW
1 stop9h 13mDelta
lun. 12/81:50 pmMDW - ANC
2 stops15h 03mDelta
Deal found 10/28$363
This Delta deal was found by Cheapflights users on 10/26. 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.
lun. 11/1712:30 amANC - ORD
2 stops13h 22mDelta
dom. 11/237:20 amORD - ANC
2 stops12h 22mDelta
Deal found 10/26$368
This Delta deal was found by Cheapflights users on 10/28. 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.
sáb. 11/226:05 amANC - ORD
1 stop7h 47mDelta
dom. 12/76:10 pmORD - ANC
1 stop10h 43mDelta
Deal found 10/28$378
This Alaska Airlines deal was found by Cheapflights users on 10/28. 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.
mar. 12/21:20 amANC - ORD
1 stop8h 49mAlaska Airlines
vie. 12/53:35 pmORD - ANC
1 stop12h 16mAlaska Airlines
Deal found 10/28$408
This Alaska Airlines deal was found by Cheapflights users on 10/27. 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.
sáb. 11/221:25 amANC - ORD
1 stop24h 36mAlaska Airlines
vie. 11/287:00 amORD - ANC
1 stop13h 31mAlaska Airlines
Deal found 10/27$411
This Delta deal was found by Cheapflights users on 10/26. 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.
mar. 11/186:05 amANC - MDW
1 stop9h 13mDelta
dom. 11/239:34 amMDW - ANC
2 stops16h 15mDelta
Deal found 10/26$425
This Delta deal was found by Cheapflights users on 10/26. 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.
mié. 11/199:45 pmANC - MDW
1 stop8h 16mDelta
lun. 12/11:47 pmMDW - ANC
1 stop14h 09mDelta
Deal found 10/26$470
This Delta deal was found by Cheapflights users on 10/26. 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.
dom. 11/2312:30 amANC - MDW
2 stops14h 38mDelta
mar. 12/21:14 pmMDW - ANC
2 stops15h 40mDelta
Deal found 10/26$480

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 octubre 28, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$338
(United Airlines)

One-way from

$169
(Alaska Airlines)

Popular in

March

Cheapest in

November

Average price

$398

Good round-trip deal

$442 or less

Good one-way deal

$279 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. 16% potential increase in price ($101 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($15 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in October 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 octubre 28, 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

lun. 1/12

1:20 am-1:22 pm

1 stop9h 02m

Chicago O'Hare Intl

dom. 2/8

6:12 am-6:58 pm

1 stop15h 46m

$358

AnchorageChicago

ANC - ORD

ANCORD

Anchorage

mié. 3/25

8:00 am-11:58 pm

1 stop12h 58m

Chicago O'Hare Intl

dom. 3/29

7:00 am-12:17 am

1 stop20h 17m

$358

AnchorageChicago

ANC - ORD

ANCORD

Anchorage

lun. 11/17

12:30 am-1:34 pm

1 stop10h 04m

Chicago O'Hare Intl

dom. 11/23

6:13 pm-1:57 am

1 stop10h 44m

$358

AnchorageChicago

ANC - ORD

ANCORD

Anchorage

lun. 11/17

12:30 am-5:18 pm

1 stop13h 48m

Chicago O'Hare Intl

vie. 11/28

7:47 am-4:42 pm

1 stop11h 55m

$358

AnchorageChicago

ANC - ORD

ANCORD

Anchorage

dom. 12/14

12:30 am-1:33 pm

1 stop10h 03m

Chicago O'Hare Intl

vie. 12/19

8:50 am-7:04 pm

1 stop13h 14m

$358

AnchorageChicago

ANC - ORD

ANCORD

Anchorage

vie. 12/5

5:55 am-11:59 pm

1 stop15h 04m

Chicago O'Hare Intl

lun. 12/8

5:42 pm-12:57 am

1 stop10h 15m

$358

AnchorageChicago

ANC - MDW

ANCMDW

Anchorage

lun. 12/8

9:45 pm-1:10 pm

1 stop12h 25m

Chicago Midway

jue. 12/11

9:59 am-7:04 pm

1 stop12h 05m

$358

AnchorageChicago

ANC - MDW

ANCMDW

Anchorage

vie. 12/12

6:05 am-6:18 pm

1 stop9h 13m

Chicago Midway

dom. 12/28

11:48 am-6:49 pm

1 stop10h 01m

$358

AnchorageChicago

ANC - MDW

ANCMDW

Anchorage

sáb. 12/6

6:05 am-6:18 pm

1 stop9h 13m

Chicago Midway

lun. 12/15

7:02 pm-12:57 am

1 stop8h 55m

$358

AnchorageChicago

ANC - MDW

ANCMDW

Anchorage

vie. 12/5

6:05 am-6:18 pm

1 stop9h 13m

Chicago Midway

lun. 12/8

7:02 pm-12:57 am

1 stop8h 55m

$358

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/25

Showing 1-10 of 26 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 October.
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

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 October 24, 2025.

Booking 51 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, 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 July is currently the most expensive (average of $452). 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 octubre 28, 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 49% 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

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

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 octubre 28, 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
11,199 reviews

Crew

8.5

Boarding

8.1

Food

7.1

Comfort

7.8

Entertainment

7.0

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Anonymous,Sep 2025

BOS - HNL

The flight was awesome but a little long. I would prefer a flight with a layover. The amount of space available was minimal and a little uncomfortable for that long of a flight.
Alaska Airlines
8.0
Very good
11,199 reviews
Alaska Airlines
8.0
Very good
11,199 reviews

Crew

8.5

Boarding

8.1

Food

7.1

Comfort

7.8

Entertainment

7.0

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Anonymous,Sep 2025

BOS - HNL

The flight was awesome but a little long. I would prefer a flight with a layover. The amount of space available was minimal and a little uncomfortable for that long of a flight.
Delta
7.9
Good
7,995 reviews
Alaska Airlines
8.0
Very good
11,199 reviews

Crew

8.5

Boarding

8.1

Food

7.1

Comfort

7.8

Entertainment

7.0

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Anonymous,Sep 2025

BOS - HNL

The flight was awesome but a little long. I would prefer a flight with a layover. The amount of space available was minimal and a little uncomfortable for that long of a flight.
Hawaiian Airlines
7.8
Good
2,794 reviews
Alaska Airlines
8.0
Very good
11,199 reviews

Crew

8.5

Boarding

8.1

Food

7.1

Comfort

7.8

Entertainment

7.0

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Anonymous,Sep 2025

BOS - HNL

The flight was awesome but a little long. I would prefer a flight with a layover. The amount of space available was minimal and a little uncomfortable for that long of a flight.
United Airlines
7.4
Good
8,996 reviews
Alaska Airlines
8.0
Very good
11,199 reviews

Crew

8.5

Boarding

8.1

Food

7.1

Comfort

7.8

Entertainment

7.0

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Anonymous,Sep 2025

BOS - HNL

The flight was awesome but a little long. I would prefer a flight with a layover. The amount of space available was minimal and a little uncomfortable for that long of a flight.

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 5 different airlines.

  • How long is the flight from Anchorage to Chicago?

    Departing from Anchorage to Chicago will take you 6h 02m. 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 United Airlines and Delta, with the lowest prices starting at $254 and $259, 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 United Airlines ($169), Alaska Airlines ($178), 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%), Air Canada (86%), Qatar Airways (86%).

  • What are the cheapest flights from Anchorage to Chicago?

    Looking at all options, your cheapest flight can be booked for $158. While the most popular route (Anchorage - Chicago O'Hare Intl) can be booked for $338 on average, our data indicates $1,111 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 July is currently the most expensive (average of $452). 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
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 octubre 28, 2025.
AirlineCheapestAverageFlexibilityOn-time
Hawaiian AirlinesCheapest$187Average$461FlexibilityNo cancel feeOn-time85%
United AirlinesCheapest$254Average$482FlexibilityNo cancel feeOn-time69%
DeltaCheapest$259Average$430FlexibilityNo cancel feeOn-timeN/A
Alaska AirlinesCheapest$318Average$501FlexibilityNo cancel feeOn-time75%
American AirlinesCheapest$338Average$513FlexibilityNo cancel feeOn-time71%

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