HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Chicago

$147+ 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 5/19. Fares are subject to change and may not be available on all flights or dates of travel.
ANC — CHI
Apr 15 — Apr 221
Wed 4/15
Wed 4/22
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Anchorage to Chicago with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

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 March 16, 2026.

This United Airlines deal was found by Cheapflights users on 3/12. 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.
Tue 4/78:50 pm
ANC
-
ORD
Nonstop6h 15m
United Airlines
Wed 4/84:03 pm
ORD
-
ANC
Nonstop6h 45m
United Airlines
Deal found 3/12$332
This Trip.com deal was found by Cheapflights users on 3/12. 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.
Sun 4/2610:26 am
ANC
-
ORD
1 stop10h 33m
Alaska Airlines
Sun 5/36:00 am
ORD
-
ANC
1 stop18h 43m
Alaska Airlines
Deal found 3/12$339
This Delta deal was found by Cheapflights users on 3/11. 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 4/76:15 am
ANC
-
ORD
1 stop15h 25m
Delta
Wed 4/86:15 am
ORD
-
ANC
1 stop15h 36m
Delta
Deal found 3/11$357
This Delta deal was found by Cheapflights users on 3/11. 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 4/249:15 pm
ANC
-
MDW
1 stop8h 51m
Delta
Mon 4/279:29 am
MDW
-
ANC
1 stop12h 17m
Delta
Deal found 3/11$357
This Trip.com deal was found by Cheapflights users on 3/13. 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.
Mon 4/2710:26 am
ANC
-
ORD
1 stop10h 33m
Alaska Airlines
Mon 5/48:48 pm
ORD
-
ANC
1 stop17h 23m
Alaska Airlines
Deal found 3/13$365
This Alaska Airlines deal was found by Cheapflights users on 3/12. 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.
Sat 5/1612:07 pm
ANC
-
ORD
1 stop32h 48m
Alaska Airlines
Tue 5/199:00 am
ORD
-
ANC
2 stops18h 46m
Alaska Airlines
Deal found 3/12$366
This United Airlines deal was found by Cheapflights users on 3/12. 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 4/98:50 pm
ANC
-
ORD
Nonstop6h 15m
United Airlines
Sun 4/124:03 pm
ORD
-
ANC
Nonstop6h 45m
United Airlines
Deal found 3/12$370
This Trip.com deal was found by Cheapflights users on 3/14. 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.
Sat 4/116:00 am
ANC
-
ORD
1 stop21h 39m
Alaska Airlines
Sat 4/186:00 am
ORD
-
ANC
1 stop20h 35m
Alaska Airlines
Deal found 3/14$373
This Alaska Airlines deal was found by Cheapflights users on 3/15. 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.
Mon 4/139:21 am
ANC
-
ORD
1 stop18h 18m
Alaska Airlines
Tue 4/147:24 pm
ORD
-
ANC
1 stop18h 14m
Alaska Airlines
Deal found 3/15$377
This Delta deal was found by Cheapflights users on 3/16. 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.
Wed 4/153:45 pm
ANC
-
MDW
2 stops14h 02m
Delta
Tue 4/219:29 am
MDW
-
ANC
1 stop12h 17m
Delta
Deal found 3/16$382
This Delta deal was found by Cheapflights users on 3/12. 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 5/76:00 am
ANC
-
MDW
1 stop8h 56m
Delta
Wed 5/131:59 pm
MDW
-
ANC
1 stop13h 32m
Delta
Deal found 3/12$383
This Delta deal was found by Cheapflights users on 3/14. 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 4/299:15 pm
ANC
-
MDW
1 stop8h 31m
Delta
Sat 5/211:18 am
MDW
-
ANC
1 stop10h 31m
Delta
Deal found 3/14$397

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 March 16, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$332
(United Airlines)

One-way from

$147
(SmartFares)

Popular in

April

Cheapest in

October

Average price

$429

Good round-trip deal

$477 or less

Good one-way deal

$258 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. 13% potential increase in price ($71 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($13 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in March 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 March 16, 2026.
Use the filters below to find and compare flights from Anchorage to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

AnchorageChicago

ANC - ORD

ANCORD

Anchorage

Tue 4/7

6:15 am-12:40 am

1 stop15h 25m

Chicago O'Hare Intl

Wed 4/8

6:15 am-6:51 pm

1 stop15h 36m

$357

AnchorageChicago

ANC - ORD

ANCORD

Anchorage

Fri 4/24

7:00 am-11:59 pm

1 stop13h 59m

Chicago O'Hare Intl

Mon 4/27

8:48 pm-9:44 am

1 stop15h 56m

$357

AnchorageChicago

ANC - ORD

ANCORD

Anchorage

Mon 4/13

5:00 pm-6:39 am

1 stop10h 39m

Chicago O'Hare Intl

Tue 4/14

7:24 pm-10:38 am

1 stop18h 14m

$357

AnchorageChicago

ANC - ORD

ANCORD

Anchorage

Fri 4/24

3:45 pm-10:19 am

2 stops15h 34m

Chicago O'Hare Intl

Mon 4/27

12:46 pm-12:25 am

1 stop14h 39m

$362

AnchorageChicago

ANC - MDW

ANCMDW

Anchorage

Fri 4/24

9:15 pm-9:06 am

1 stop8h 51m

Chicago Midway

Mon 4/27

2:12 pm-12:25 am

2 stops13h 13m

$362

AnchorageChicago

ANC - MDW

ANCMDW

Anchorage

Tue 4/28

9:15 pm-4:26 pm

2 stops16h 11m

Chicago Midway

Mon 5/4

6:00 am-6:46 pm

2 stops15h 46m

$367

AnchorageChicago

ANC - ORD

ANCORD

Anchorage

Sat 5/16

11:08 pm-8:25 am

Nonstop6h 17m

Chicago O'Hare Intl

Tue 5/19

9:00 am-12:46 am

2 stops18h 46m

$377

AnchorageChicago

ANC - MDW

ANCMDW

Anchorage

Thu 5/7

6:00 am-5:56 pm

1 stop8h 56m

Chicago Midway

Wed 5/13

1:59 pm-12:31 am

1 stop13h 32m

$383
Quickest round-trip

AnchorageChicago

ANC - ORD

ANCORD

Anchorage

Tue 4/7

8:50 pm-6:05 am

Nonstop6h 15m

Chicago O'Hare Intl

Sat 4/11

4:03 pm-7:48 pm

Nonstop6h 45m

$397

AnchorageChicago

ANC - ORD

ANCORD

Anchorage

Fri 9/11

6:00 am-11:59 pm

1 stop14h 59m

Chicago O'Hare Intl

Sun 9/13

6:00 am-5:36 pm

1 stop14h 36m

$409

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/11

Showing 1-10 of 33 resultsSorted by cheapest first
1
2
3
4

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 March.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
CheapTicketsDealPrice 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 $697). 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 March 16, 2026.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Anchorage to Chicago as you normally would.

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 March 16, 2026.

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

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
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 March 16, 2026.
Get a feel of what it's like to fly with Alaska Airlines,Delta, andHawaiian 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
7.9
Good
12,054 reviews

Comfort

7.8

Crew

8.5

Food

7.1

Overall

7.9

Boarding

8.1

Entertainment

7.0

Reviews

1 / 20
10.0
Excellent

Franzi,Mar 2026

SFO - PDX

I love flying with Alaska. I think they sre the best airline.
Alaska Airlines
7.9
Good
12,054 reviews
Alaska Airlines
7.9
Good
12,054 reviews

Comfort

7.8

Crew

8.5

Food

7.1

Overall

7.9

Boarding

8.1

Entertainment

7.0

Reviews

1 / 20
10.0
Excellent

Franzi,Mar 2026

SFO - PDX

I love flying with Alaska. I think they sre the best airline.
Delta
7.9
Good
8,299 reviews
Alaska Airlines
7.9
Good
12,054 reviews

Comfort

7.8

Crew

8.5

Food

7.1

Overall

7.9

Boarding

8.1

Entertainment

7.0

Reviews

1 / 20
10.0
Excellent

Franzi,Mar 2026

SFO - PDX

I love flying with Alaska. I think they sre the best airline.
Hawaiian Airlines
7.8
Good
2,839 reviews
Alaska Airlines
7.9
Good
12,054 reviews

Comfort

7.8

Crew

8.5

Food

7.1

Overall

7.9

Boarding

8.1

Entertainment

7.0

Reviews

1 / 20
10.0
Excellent

Franzi,Mar 2026

SFO - PDX

I love flying with Alaska. I think they sre the best airline.
United Airlines
7.4
Good
9,427 reviews
Alaska Airlines
7.9
Good
12,054 reviews

Comfort

7.8

Crew

8.5

Food

7.1

Overall

7.9

Boarding

8.1

Entertainment

7.0

Reviews

1 / 20
10.0
Excellent

Franzi,Mar 2026

SFO - PDX

I love flying with Alaska. I think they sre the best airline.

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 2 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 13h 59m. 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 United Airlines and Alaska Airlines, with the lowest prices starting at $262 and $318, respectively. These flights start at 64% 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: Korean Air (71%), Air Canada (50%), Qantas Airways (50%).

  • What are the cheapest flights from Anchorage to Chicago?

    Looking at all options, your cheapest flight can be booked for $160. While the most popular route (Anchorage - Chicago O'Hare Intl) can be booked for $397 on average, our data indicates $781 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 $697). 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

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Anchorage to Chicago

See prices for flight routes from nearby airports that may be better suited for you.
Anchorage to O'Hare Intl flights
Anchorage to St. Louis flights
Fairbanks to O'Hare Intl flights
Anchorage to Evansville flights
Fairbanks to St. Louis flights
Fairbanks to Peoria flights

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 March 16, 2026.
AirlineCheapestAverageFlexibilityOn-time
Hawaiian AirlinesCheapest$158Average$461FlexibilityNo cancel feeOn-time85%
United AirlinesCheapest$262Average$474FlexibilityNo cancel feeOn-time69%
Alaska AirlinesCheapest$318Average$484FlexibilityNo cancel feeOn-time75%
DeltaCheapest$337Average$428FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$338Average$513FlexibilityNo cancel feeOn-time71%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.