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$166+ 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 6/17. Fares are subject to change and may not be available on all flights or dates of travel.
ANC — CHI
Feb 26 — Mar 51
Thu 2/26
Thu 3/5
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 January 27, 2026.

This Orbitz deal was found by Cheapflights users on 1/25. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/2211:23 pm
ANC
-
ORD
Nonstop6h 17m
Alaska Airlines
Wed 6/37:45 pm
ORD
-
ANC
1 stop17h 01m
Alaska Airlines
Deal found 1/25$349
This Alaska Airlines deal was found by Cheapflights users on 1/26. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/1111:24 pm
ANC
-
ORD
Nonstop6h 16m
Alaska Airlines
Sat 6/137:20 am
ORD
-
ANC
1 stop29h 49m
Alaska Airlines
Deal found 1/26$352
This Alaska Airlines deal was found by Cheapflights users on 1/26. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/186:00 am
ANC
-
ORD
1 stop14h 59m
Alaska Airlines
Wed 3/257:24 pm
ORD
-
ANC
1 stop20h 17m
Alaska Airlines
Deal found 1/26$359
This Delta deal was found by Cheapflights users on 1/26. 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.
Wed 3/189:15 pm
ANC
-
MDW
1 stop8h 35m
Delta
Wed 3/259:30 am
MDW
-
ANC
1 stop12h 21m
Delta
Deal found 1/26$359
This Alaska Airlines deal was found by Cheapflights users on 1/26. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/251:08 am
ANC
-
ORD
2 stops12h 25m
Alaska Airlines
Tue 3/33:54 pm
ORD
-
ANC
1 stop12h 15m
Alaska Airlines
Deal found 1/26$364
This Delta deal was found by Cheapflights users on 1/24. 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 3/199:15 pm
ANC
-
MDW
1 stop8h 35m
Delta
Mon 3/239:30 am
MDW
-
ANC
2 stops17h 59m
Delta
Deal found 1/24$364
This Alaska Airlines deal was found by Cheapflights users on 1/26. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/612:59 am
ANC
-
ORD
2 stops15h 04m
Alaska Airlines
Wed 5/139:00 am
ORD
-
ANC
2 stops16h 36m
Alaska Airlines
Deal found 1/26$369
This Delta deal was found by Cheapflights users on 1/26. 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.
Fri 2/203:21 pm
ANC
-
MDW
2 stops18h 25m
Delta
Sun 2/229:34 am
MDW
-
ANC
2 stops17h 35m
Delta
Deal found 1/26$369
This Delta deal was found by Cheapflights users on 1/25. 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 3/231:34 am
ANC
-
ORD
1 stop8h 51m
Delta
Sat 3/282:20 pm
ORD
-
ANC
1 stop10h 58m
Delta
Deal found 1/25$378
This Delta deal was found by Cheapflights users on 1/26. 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.
Thu 5/79:55 pm
ANC
-
MDW
1 stop7h 43m
Delta
Wed 5/132:00 pm
MDW
-
ANC
1 stop13h 33m
Delta
Deal found 1/26$378
This Delta deal was found by Cheapflights users on 1/24. 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 3/209:15 pm
ANC
-
ORD
1 stop11h 15m
Delta
Mon 3/231:19 pm
ORD
-
ANC
2 stops14h 10m
Delta
Deal found 1/24$383
This Delta deal was found by Cheapflights users on 1/24. 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 3/186:15 am
ANC
-
ORD
2 stops12h 19m
Delta
Mon 3/231:19 pm
ORD
-
ANC
2 stops14h 10m
Delta
Deal found 1/24$388

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 January 27, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$349
(Orbitz)

One-way from

$166
(Kiwi.com)

Popular in

March

Cheapest in

October

Average price

$524

Good round-trip deal

$518 or less

Good one-way deal

$306 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. 15% potential increase in price ($88 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($19 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 2026
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 January 27, 2026.
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 6/11

9:22 pm-6:40 am

Nonstop6h 18m

Chicago O'Hare Intl

Sat 6/13

7:20 am-10:09 am

1 stop29h 49m

$352

AnchorageChicago

ANC - ORD

ANCORD

Anchorage

Sun 4/12

1:30 am-1:23 pm

1 stop8h 53m

Chicago O'Hare Intl

Sun 4/19

8:50 am-6:46 pm

1 stop12h 56m

$359

AnchorageChicago

ANC - ORD

ANCORD

Anchorage

Wed 3/18

6:00 am-6:26 pm

1 stop9h 26m

Chicago O'Hare Intl

Wed 3/25

7:24 pm-9:26 am

1 stop17h 02m

$359

AnchorageChicago

ANC - ORD

ANCORD

Anchorage

Wed 3/18

1:34 am-1:25 pm

1 stop8h 51m

Chicago O'Hare Intl

Mon 3/23

7:25 am-2:45 pm

1 stop10h 20m

$359

AnchorageChicago

ANC - ORD

ANCORD

Anchorage

Tue 4/14

6:00 am-11:58 pm

1 stop14h 58m

Chicago O'Hare Intl

Sun 4/19

8:50 am-6:46 pm

1 stop12h 56m

$359

AnchorageChicago

ANC - ORD

ANCORD

Anchorage

Thu 5/7

5:25 pm-6:40 am

1 stop10h 15m

Chicago O'Hare Intl

Wed 5/13

7:45 pm-9:46 am

1 stop17h 01m

$359

AnchorageChicago

ANC - ORD

ANCORD

Anchorage

Wed 4/15

6:00 am-11:58 pm

1 stop14h 58m

Chicago O'Hare Intl

Mon 4/20

6:00 pm-12:25 am

1 stop9h 25m

$359

AnchorageChicago

ANC - ORD

ANCORD

Anchorage

Mon 4/13

9:15 pm-8:38 am

1 stop8h 23m

Chicago O'Hare Intl

Mon 4/20

12:46 pm-8:37 pm

1 stop10h 51m

$359

AnchorageChicago

ANC - ORD

ANCORD

Anchorage

Fri 3/20

9:15 pm-8:52 am

1 stop8h 37m

Chicago O'Hare Intl

Mon 3/23

7:25 am-2:45 pm

1 stop10h 20m

$359

AnchorageChicago

ANC - MDW

ANCMDW

Anchorage

Tue 3/24

9:15 pm-1:25 pm

1 stop13h 10m

Chicago Midway

Sat 3/28

9:30 am-6:51 pm

1 stop12h 21m

$359

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/26

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 January.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust 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.

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 $650). 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.

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
Our travel experts
Ramsey Qubein

Ramsey Qubein

Expert on ORD

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 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 January 27, 2026.
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
11,795 reviews

Crew

8.5

Food

7.1

Comfort

7.8

Overall

8.0

Boarding

8.1

Entertainment

7.0

Reviews

1 / 20
10.0
Excellent

Anonymous,Jan 2026

STS - LAX

Enjoyed staff assistance from ticking thru tsa , boarding and in the plane Couldn’t pick a seat except upgrading
Alaska Airlines
8.0
Very good
11,795 reviews
Alaska Airlines
8.0
Very good
11,795 reviews

Crew

8.5

Food

7.1

Comfort

7.8

Overall

8.0

Boarding

8.1

Entertainment

7.0

Reviews

1 / 20
10.0
Excellent

Anonymous,Jan 2026

STS - LAX

Enjoyed staff assistance from ticking thru tsa , boarding and in the plane Couldn’t pick a seat except upgrading
Delta
7.9
Good
8,119 reviews
Alaska Airlines
8.0
Very good
11,795 reviews

Crew

8.5

Food

7.1

Comfort

7.8

Overall

8.0

Boarding

8.1

Entertainment

7.0

Reviews

1 / 20
10.0
Excellent

Anonymous,Jan 2026

STS - LAX

Enjoyed staff assistance from ticking thru tsa , boarding and in the plane Couldn’t pick a seat except upgrading
Hawaiian Airlines
7.8
Good
2,829 reviews
Alaska Airlines
8.0
Very good
11,795 reviews

Crew

8.5

Food

7.1

Comfort

7.8

Overall

8.0

Boarding

8.1

Entertainment

7.0

Reviews

1 / 20
10.0
Excellent

Anonymous,Jan 2026

STS - LAX

Enjoyed staff assistance from ticking thru tsa , boarding and in the plane Couldn’t pick a seat except upgrading
United Airlines
7.4
Good
9,205 reviews
Alaska Airlines
8.0
Very good
11,795 reviews

Crew

8.5

Food

7.1

Comfort

7.8

Overall

8.0

Boarding

8.1

Entertainment

7.0

Reviews

1 / 20
10.0
Excellent

Anonymous,Jan 2026

STS - LAX

Enjoyed staff assistance from ticking thru tsa , boarding and in the plane Couldn’t pick a seat except upgrading

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 6h 18m. 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 $220 and $254, respectively. These flights start at 66% 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 Alaska Airlines ($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: Qantas Airways (100%), Korean Air (84%), Air Canada (74%).

  • What are the cheapest flights from Anchorage to Chicago?

    Looking at all options, your cheapest flight can be booked for $169. While the most popular route (Anchorage - Chicago O'Hare Intl) can be booked for $351 on average, our data indicates $725 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 $650). 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 January 27, 2026.
AirlineCheapestAverageFlexibilityOn-time
Hawaiian AirlinesCheapest$158Average$461FlexibilityNo cancel feeOn-time85%
DeltaCheapest$220Average$395FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$254Average$488FlexibilityNo cancel feeOn-time69%
Alaska AirlinesCheapest$318Average$492FlexibilityNo cancel feeOn-time75%
American AirlinesCheapest$338Average$513FlexibilityNo cancel feeOn-time71%

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