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Anchorage

$201+ Cheap flights from Chicago (CHI) to Anchorage (ANC)

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 8/12. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — ANC
Jun 19 — Jun 261
Fri 6/19
Fri 6/26
1 adult, Economy
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Find cheap flights from Chicago to Anchorage with Cheapflights

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Cheapflights Tip: The best prices from Chicago to Anchorage are usually found in October or February, booked 79 days in advance, depart on a Friday or Wednesday and return on a Tuesday

Cheap flight deals from Chicago to Anchorage

Cheapest flights from Chicago to Anchorage
Explore the most affordable flight options available from Chicago to Anchorage. Find the lowest fares from popular airlines and budget airlines, with prices last updated on May 20, 2026.

This Alaska Airlines deal was found by Cheapflights users on 5/18. 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 6/2512:59 am
ORD
-
ANC
Nonstop6h 42m
Alaska Airlines
Wed 7/11:22 am
ANC
-
ORD
1 stop24h 38m
Alaska Airlines
Deal found 5/18$399
This Delta deal was found by Cheapflights users on 5/18. 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 7/205:55 pm
ORD
-
ANC
1 stop19h 26m
Delta
Wed 7/221:30 am
ANC
-
ORD
2 stops17h 18m
Delta
Deal found 5/18$400
This Delta deal was found by Cheapflights users on 5/19. 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.
Sat 8/297:25 pm
MDW
-
ANC
1 stop8h 34m
Delta
Tue 9/89:55 pm
ANC
-
MDW
2 stops11h 35m
Delta
Deal found 5/19$400
This Delta deal was found by Cheapflights users on 5/17. 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.
Sat 7/189:49 am
MDW
-
ANC
2 stops27h 32m
Delta
Thu 7/2312:44 pm
ANC
-
MDW
1 stop16h 53m
Delta
Deal found 5/17$401
This Delta deal was found by Cheapflights users on 5/19. 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.
Sat 7/256:55 pm
MDW
-
ANC
1 stop29h 05m
Delta
Mon 7/276:00 am
ANC
-
MDW
2 stops24h 08m
Delta
Deal found 5/19$402
This Delta deal was found by Cheapflights users on 5/17. 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.
Sat 7/189:49 am
MDW
-
ANC
2 stops27h 32m
Delta
Tue 7/2112:44 pm
ANC
-
MDW
1 stop26h 34m
Delta
Deal found 5/17$403
This Expedia deal was found by Cheapflights users on 5/18. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/912:59 am
ORD
-
ANC
Nonstop6h 42m
Alaska Airlines
Sun 8/2310:28 pm
ANC
-
ORD
Nonstop6h 12m
Alaska Airlines
Deal found 5/18$404
This Delta deal was found by Cheapflights users on 5/18. 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 8/272:12 pm
ORD
-
ANC
2 stops13h 47m
Delta
Tue 9/89:55 pm
ANC
-
ORD
2 stops11h 44m
Delta
Deal found 5/18$405
This Delta deal was found by Cheapflights users on 5/18. 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 7/241:49 pm
MDW
-
ANC
2 stops23h 32m
Delta
Wed 7/2910:10 pm
ANC
-
MDW
2 stops17h 15m
Delta
Deal found 5/18$405
This Delta deal was found by Cheapflights users on 5/18. 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.
Sat 6/135:55 pm
ORD
-
ANC
1 stop19h 25m
Delta
Thu 6/1810:30 pm
ANC
-
ORD
1 stop16h 59m
Delta
Deal found 5/18$406
This Delta deal was found by Cheapflights users on 5/16. 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.
Sat 6/131:49 pm
MDW
-
ANC
1 stop14h 06m
Delta
Mon 6/2212:35 pm
ANC
-
MDW
1 stop17h 02m
Delta
Deal found 5/16$406
This Delta deal was found by Cheapflights users on 5/19. 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 8/26:55 am
ORD
-
ANC
1 stop20h 03m
Delta
Wed 8/51:32 am
ANC
-
ORD
1 stop12h 11m
Delta
Deal found 5/19$407

Find flight deals from Chicago to Anchorage

Discover tips and strategies to find the most affordable flight options for your journey from Chicago (CHI) to Anchorage (ANC). 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 May 20, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$399
(Alaska Airlines)

One-way from

$201
(United Airlines)

Popular in

June

Cheapest in

October

Average price

$474

Good round-trip deal

$474 or less

Good one-way deal

$245 or less
Provider with most accurate pricing for Chicago (CHI)-Anchorage flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago (CHI)-Anchorage flights.
Search Deals
From Chicago (CHI) to Anchorage
Search Deals
One-way flight from Chicago (CHI) to Anchorage
Search Deals
Highest demand for flights based on searches. 15% potential increase in price ($83 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($12 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in May 2026
Search Deals
Price to beat on a round-trip flight from Chicago (CHI) to Anchorage.
Search Deals
Price to beat on a one-way flight from Chicago (CHI) to Anchorage.
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Chicago to Anchorage 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 May 20, 2026.
Use the filters below to find and compare flights from Chicago to Anchorage that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoAnchorage

MDW - ANC

MDWANC

Chicago Midway

Tue 8/11

1:52 pm-11:24 pm

2 stops12h 32m

Anchorage

Mon 8/17

1:32 am-6:33 pm

2 stops14h 01m

$405

ChicagoAnchorage

ORD - ANC

ORDANC

Chicago O'Hare Intl

Tue 9/1

7:20 am-11:12 am

Nonstop6h 52m

Anchorage

Tue 9/1

1:29 am-11:59 pm

1 stop19h 30m

$423

ChicagoAnchorage

ORD - ANC

ORDANC

Chicago O'Hare Intl

Fri 6/5

5:00 am-11:10 am

1 stop9h 10m

Anchorage

Fri 6/12

11:59 pm-9:19 am

Nonstop6h 20m

$427

ChicagoAnchorage

ORD - ANC

ORDANC

Chicago O'Hare Intl

Wed 6/24

6:55 am-4:15 pm

1 stop12h 20m

Anchorage

Wed 7/1

8:15 am-11:39 pm

1 stop12h 24m

$428
Quickest round-trip

ChicagoAnchorage

ORD - ANC

ORDANC

Chicago O'Hare Intl

Wed 6/24

12:59 am-4:41 am

Nonstop6h 42m

Anchorage

Tue 7/7

11:15 pm-8:29 am

Nonstop6h 14m

$431

ChicagoAnchorage

ORD - ANC

ORDANC

Chicago O'Hare Intl

Fri 8/21

2:18 pm-2:17 pm

1 stop26h 59m

Anchorage

Sun 8/30

10:28 pm-7:40 am

Nonstop6h 12m

$434

ChicagoAnchorage

ORD - ANC

ORDANC

Chicago O'Hare Intl

Sat 6/27

6:35 am-6:45 pm

1 stop15h 10m

Anchorage

Fri 7/3

6:00 am-11:39 pm

1 stop14h 39m

$468

ChicagoAnchorage

ORD - ANC

ORDANC

Chicago O'Hare Intl

Fri 7/31

6:55 am-8:08 pm

1 stop16h 13m

Anchorage

Wed 8/5

10:37 pm-4:24 pm

1 stop14h 47m

$473

ChicagoAnchorage

ORD - ANC

ORDANC

Chicago O'Hare Intl

Tue 6/23

12:59 am-4:41 am

Nonstop6h 42m

Anchorage

Wed 7/1

5:00 am-5:00 am

1 stop21h 00m

$479

ChicagoAnchorage

ORD - ANC

ORDANC

Chicago O'Hare Intl

Sat 8/15

2:27 pm-12:59 am

2 stops13h 32m

Anchorage

Sat 8/22

10:08 pm-4:24 pm

2 stops15h 16m

$493

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/16

Showing 1-10 of 40 resultsSorted by cheapest first
1
2
3
4

Compare providers for flights from Chicago to Anchorage

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 Chicago to Anchorage in May.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
PricelinePrice Accuracy1 starTrust 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 Chicago-Anchorage flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Chicago-Anchorage flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Chicago-Anchorage flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Chicago-Anchorage 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 Chicago-Anchorage 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 Chicago to Anchorage

Have a flexible travel schedule? Discover the best time to fly to Anchorage from Chicago 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 Chicago to Anchorage

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

Currently, September is the cheapest month in which you can book a flight from Chicago to Anchorage (average of $68). Flying from Chicago to Anchorage in February is currently the most expensive (average of $352). 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 CHI to ANC?

Find hourly flight availability from Chicago to Anchorage. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated May 20, 2026.

Unlike at noon, when flights are generally more expensive, you can save up to 41% on flights from Chicago to Anchorage by exploring options for tickets in the afternoon.

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

How far ahead should I book a flight from Chicago to Anchorage?

Booking 86 days in advance of your planned departure date is, on average, the best time to get cheap flights from Chicago to Anchorage. The general trend is that the closer you book to the departure date, the more expensive your flight will be.

What is the cheapest day to fly from Chicago to Anchorage?

Use this chart to determine the cheapest time to fly round-trip from Chicago to Anchorage. Price data was last updated on May 16, 2026.

Travelers seeking maximum savings on their Chicago to Anchorage flight should consider departing on Friday at noon when fares are most often at their lowest. Tuesday at noon flights should be avoided if possible as fares are typically the most expensive at this time.

The best insider tips for Chicago to Anchorage 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 Chicago to Anchorage 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 Anchorage

Get insights into the airlines that provide service to Anchorage. 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 Anchorage. Reviews last updated May 20, 2026.
Peruse reviews from past customers who have flown with Alaska Airlines,Delta, andHawaiian Airlines from Chicago to Anchorage to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Alaska Airlines
7.9
Good
12,385 reviews

Boarding

8.1

Food

7.0

Comfort

7.8

Overall

7.9

Crew

8.5

Entertainment

7.0

Reviews

1 / 20
8.0
Excellent

Eugene,Mar 2026

MFR - SEA

Alaska Airlines is is always good. There where few choices of what to drink, and no food. No blankets, no pillows, and you h ats ok. I just had open heart surgery And i could have used something. But the flight and the crew where exelent. So all is well
Alaska Airlines
7.9
Good
12,385 reviews
Alaska Airlines
7.9
Good
12,385 reviews

Boarding

8.1

Food

7.0

Comfort

7.8

Overall

7.9

Crew

8.5

Entertainment

7.0

Reviews

1 / 20
8.0
Excellent

Eugene,Mar 2026

MFR - SEA

Alaska Airlines is is always good. There where few choices of what to drink, and no food. No blankets, no pillows, and you h ats ok. I just had open heart surgery And i could have used something. But the flight and the crew where exelent. So all is well
Delta
7.9
Good
8,452 reviews
Alaska Airlines
7.9
Good
12,385 reviews

Boarding

8.1

Food

7.0

Comfort

7.8

Overall

7.9

Crew

8.5

Entertainment

7.0

Reviews

1 / 20
8.0
Excellent

Eugene,Mar 2026

MFR - SEA

Alaska Airlines is is always good. There where few choices of what to drink, and no food. No blankets, no pillows, and you h ats ok. I just had open heart surgery And i could have used something. But the flight and the crew where exelent. So all is well
Hawaiian Airlines
7.8
Good
2,836 reviews
Alaska Airlines
7.9
Good
12,385 reviews

Boarding

8.1

Food

7.0

Comfort

7.8

Overall

7.9

Crew

8.5

Entertainment

7.0

Reviews

1 / 20
8.0
Excellent

Eugene,Mar 2026

MFR - SEA

Alaska Airlines is is always good. There where few choices of what to drink, and no food. No blankets, no pillows, and you h ats ok. I just had open heart surgery And i could have used something. But the flight and the crew where exelent. So all is well
United Airlines
7.4
Good
9,738 reviews
Alaska Airlines
7.9
Good
12,385 reviews

Boarding

8.1

Food

7.0

Comfort

7.8

Overall

7.9

Crew

8.5

Entertainment

7.0

Reviews

1 / 20
8.0
Excellent

Eugene,Mar 2026

MFR - SEA

Alaska Airlines is is always good. There where few choices of what to drink, and no food. No blankets, no pillows, and you h ats ok. I just had open heart surgery And i could have used something. But the flight and the crew where exelent. So all is well
American Airlines
7.1
Good
11,643 reviews
Alaska Airlines
7.9
Good
12,385 reviews

Boarding

8.1

Food

7.0

Comfort

7.8

Overall

7.9

Crew

8.5

Entertainment

7.0

Reviews

1 / 20
8.0
Excellent

Eugene,Mar 2026

MFR - SEA

Alaska Airlines is is always good. There where few choices of what to drink, and no food. No blankets, no pillows, and you h ats ok. I just had open heart surgery And i could have used something. But the flight and the crew where exelent. So all is well

Related info for your journey

Find useful and relevant information for your journey from Chicago to Anchorage. 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 into for flights to Anchorage from Chicago?

    For a flight from Chicago to Anchorage, you will be flying into Anchorage. Anchorage (ANC) is just 4.4 mi from the center of the city. Anchorage is the only Anchorage airport and it handles 3 inbound flights from Chicago per day. 5 airlines have flights to Anchorage from Chicago on a regular basis.

  • How long is the flight from Chicago to Anchorage?

    A quick flight from Chicago to Anchorage can take about 6h 52m. Delta provides one of the quickest options available for as low as $423. The distance between Chicago and Anchorage is about 2837 mi. 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 Chicago to Anchorage round-trip?

    Flying on Hawaiian Airlines is currently your cheapest option to Anchorage, with prices starting at $199. Additional round-trip tickets that might be worth considering are offered by Delta and United Airlines, with the lowest prices starting at $209 and $318, respectively. Hawaiian Airlines is 57% cheaper than the average price of flights available within the next 90 days to this destination.

  • What are the cheapest airlines to fly from Chicago to Anchorage one-way?

    $160 is the cheapest one-way deal found within the past few days, from Alaska Airlines. You may also be able to find cheap deals on American Airlines and Delta, with prices starting from $163 and $169, respectively.

  • What are the most reliable airlines from Chicago to Anchorage?

    Before booking your flight to Anchorage from Chicago, check out the most reliable airlines to get you to your destination on time: Qatar Airways (100%), Alaska Airlines (100%), United Airlines( 62%).

  • What are the cheapest flights from Chicago to Anchorage?

    Looking for the cheapest flight from Chicago to Anchorage? While on average our users pay $438, our data indicates the cheapest price to be $200. The most popular route (Chicago O'Hare Intl - Anchorage), is priced around $373.

  • Can I find deals for flights from Chicago to Anchorage that include hotel bookings?

    Yes. In addition to deals on Chicago to Anchorage flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Chicago to Anchorage?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Chicago to Anchorage.

  • Can I find deals for business class flights from Chicago to Anchorage?

    Yes. Cheapflights offers flight deals from Chicago to Anchorage 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 Chicago to Anchorage?

    Currently, September is the cheapest month in which you can book a flight from Chicago to Anchorage (average of $68). Flying from Chicago to Anchorage in February is currently the most expensive (average of $352). 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
Seward
Girdwood

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Top 5 airlines flying from Chicago to Anchorage

Discover the top 5 airlines that operate flights from Chicago to Anchorage. 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 May 20, 2026.
AirlineCheapestAverageFlexibilityOn-time
Hawaiian AirlinesCheapest$199Average$512FlexibilityNo cancel feeOn-time85%
DeltaCheapest$209Average$429FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$318Average$531FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$318Average$556FlexibilityNo cancel feeOn-time71%
Alaska AirlinesCheapest$338Average$518FlexibilityNo cancel feeOn-time75%

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