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$179+ Cheap flights from Chicago (CHI) to Alaska

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 1/21. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — ANC
Jan 17 — Jan 241
Sat 1/17
Sat 1/24
1 adult, Economy
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Cheap flight deals from Chicago to Alaska

Cheapest flights from Chicago to Alaska
Explore the most affordable flight options available from Chicago to Alaska. Find the lowest fares from popular airlines and budget airlines, with prices last updated on December 18, 2025.

This Delta deal was found by Cheapflights users on 12/17. 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.
Wed 12/315:30 amORD - ANC
1 stop16h 27mDelta
Tue 1/66:10 amANC - ORD
1 stop8h 45mDelta
Deal found 12/17$600
This Delta deal was found by Cheapflights users on 12/17. 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.
Wed 12/316:00 amMDW - ANC
1 stop15h 57mDelta
Tue 1/69:15 pmANC - MDW
1 stop12h 54mDelta
Deal found 12/17$600
This Delta deal was found by Cheapflights users on 12/16. 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.
Fri 12/266:45 amORD - ANC
1 stop15h 12mDelta
Tue 1/65:55 amANC - ORD
1 stop14h 58mDelta
Deal found 12/16$630
This Delta deal was found by Cheapflights users on 12/16. 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.
Fri 12/266:00 amMDW - ANC
1 stop15h 57mDelta
Tue 1/69:15 pmANC - MDW
1 stop12h 54mDelta
Deal found 12/16$630
This Delta deal was found by Cheapflights users on 12/16. 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.
Thu 12/256:00 amORD - ANC
1 stop11h 45mDelta
Wed 12/318:15 pmANC - ORD
1 stop10h 21mDelta
Deal found 12/16$690
This Delta deal was found by Cheapflights users on 12/16. 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.
Thu 12/255:59 pmMDW - ANC
1 stop10h 23mDelta
Wed 12/319:15 pmANC - MDW
1 stop10h 51mDelta
Deal found 12/16$690
This Delta deal was found by Cheapflights users on 12/17. 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.
Thu 12/251:35 pmORD - ANC
2 stops14h 47mDelta
Mon 12/298:15 pmANC - ORD
1 stop15h 58mDelta
Deal found 12/17$695
This Delta deal was found by Cheapflights users on 12/17. 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.
Wed 12/246:08 pmMDW - ANC
2 stops23h 37mDelta
Sun 1/49:15 pmANC - MDW
1 stop12h 54mDelta
Deal found 12/17$695
This Delta deal was found by Cheapflights users on 12/17. 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.
Wed 12/246:08 pmMDW - ANC
2 stops23h 37mDelta
Sat 1/36:00 amANC - MDW
1 stop26h 06mDelta
Deal found 12/17$698
This Delta deal was found by Cheapflights users on 12/17. 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.
Wed 12/246:08 pmMDW - ANC
2 stops23h 37mDelta
Fri 1/23:40 pmANC - MDW
2 stops16h 26mDelta
Deal found 12/17$702
This Delta deal was found by Cheapflights users on 12/17. 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.
Wed 12/246:02 pmORD - ANC
2 stops23h 43mDelta
Sat 1/35:45 amANC - ORD
1 stop15h 14mDelta
Deal found 12/17$719
This Delta deal was found by Cheapflights users on 12/16. 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.
Thu 12/256:00 amORD - ANC
1 stop9h 41mDelta
Tue 12/309:15 pmANC - ORD
2 stops16h 06mDelta
Deal found 12/16$720

Find flight deals from Chicago to Alaska

Keep the following information in mind while searching for Chicago to Alaska flight deals. Data was last updated December 18, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$342
(flugladen.de)

One-way from

$179
(Kiwi.com)

Popular in

June

Cheapest in

October

Average price

$488

Good round-trip deal

$398 or less

Good one-way deal

$250 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 Alaska
Search Deals
One-way flight from Chicago (CHI) to Alaska
Search Deals
Highest demand for flights based on searches. 10% potential increase in price ($61 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($10 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
Search Deals
Price to beat on a round-trip flight from Chicago (CHI) to Alaska.
Search Deals
Price to beat on a one-way flight from Chicago (CHI) to Alaska.
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Chicago to Alaska 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 December 18, 2025.
Use the filters below to find and compare flights from Chicago to Alaska that are best for you.

Fly from

Chicago

Fly to

Alaska

Route

Depart

Return

Price

ChicagoAnchorage

ORD - ANC

ORDANC

Chicago O'Hare Intl

Mon 3/9

1:00 pm-1:09 am

1 stop15h 09m

Anchorage

Fri 3/20

5:00 pm-5:00 am

1 stop9h 00m

$358

ChicagoAnchorage

ORD - ANC

ORDANC

Chicago O'Hare Intl

Sun 3/8

6:00 am-6:51 pm

1 stop15h 51m

Anchorage

Sat 3/21

9:15 pm-11:35 am

1 stop11h 20m

$358

ChicagoAnchorage

ORD - ANC

ORDANC

Chicago O'Hare Intl

Sat 2/14

7:00 am-11:04 pm

1 stop19h 04m

Anchorage

Mon 2/16

2:26 am-11:56 pm

1 stop18h 30m

$358

ChicagoAnchorage

ORD - ANC

ORDANC

Chicago O'Hare Intl

Wed 3/11

2:20 pm-12:38 am

1 stop13h 18m

Anchorage

Sat 3/21

9:15 pm-11:35 am

1 stop11h 20m

$358

ChicagoAnchorage

ORD - ANC

ORDANC

Chicago O'Hare Intl

Sun 2/22

6:15 am-6:57 pm

1 stop15h 42m

Anchorage

Thu 2/26

9:15 pm-8:40 am

1 stop8h 25m

$358

ChicagoAnchorage

ORD - ANC

ORDANC

Chicago O'Hare Intl

Fri 2/20

2:07 pm-12:30 am

1 stop13h 23m

Anchorage

Mon 2/23

1:25 am-4:33 pm

1 stop12h 08m

$358

ChicagoAnchorage

ORD - ANC

ORDANC

Chicago O'Hare Intl

Fri 2/13

3:54 pm-1:11 am

1 stop12h 17m

Anchorage

Sun 2/15

12:29 am-12:01 pm

1 stop8h 32m

$358

ChicagoAnchorage

ORD - ANC

ORDANC

Chicago O'Hare Intl

Wed 3/11

2:20 pm-12:38 am

1 stop13h 18m

Anchorage

Tue 3/17

1:34 am-1:25 pm

1 stop8h 51m

$358

ChicagoAnchorage

ORD - ANC

ORDANC

Chicago O'Hare Intl

Mon 2/2

8:00 am-10:52 pm

1 stop17h 52m

Anchorage

Fri 2/6

8:00 am-11:50 pm

1 stop12h 50m

$358

ChicagoAnchorage

MDW - ANC

MDWANC

Chicago Midway

Mon 2/2

9:53 am-6:56 pm

1 stop12h 03m

Anchorage

Sat 2/7

9:15 pm-11:05 am

1 stop10h 50m

$358

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/15

Showing 1-10 of 56 results
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Best time to book a flight from Chicago to Alaska

Have a flexible travel schedule? Discover the best time to fly to Alaska 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 Alaska

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

Currently, May is the cheapest month in which you can book a flight from Chicago to Alaska (average of $198). Flying from Chicago to Alaska in July is currently the most expensive (average of $450). 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 AK?

Find hourly flight availability from Chicago to Alaska. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated December 18, 2025.

Unlike in the afternoon, when flights are generally more expensive, you can save up to 19% on flights from Chicago to Alaska by exploring options for tickets at noon.

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

Use this chart to determine the cheapest time to fly round-trip from Chicago to Alaska. Price data was last updated on December 16, 2024.

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

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

Reviews of airlines servicing Alaska

Get insights into the airlines that provide service to Alaska. 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 Alaska. Reviews last updated December 18, 2025.
See what other customers who have flown with Alaska Airlines, Delta, and Hawaiian Airlines from Chicago to Alaska have to say. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Alaska Airlines
8.0
Very good
11,477 reviews

Crew

8.5

Boarding

8.1

Food

7.1

Overall

8.0

Entertainment

7.0

Comfort

7.8

Reviews

1 / 20
2.0
Mediocre

Art,Dec 2025

SAN - OGG

It was a five hour flight and my seat did not recline. I have had three back surgeries and I’m solid bone for my L3 vertebrae all the way to my tailbone. My body has never hurt so much. There was no TV on this flight and only a small can of soda was free.
Alaska Airlines
8.0
Very good
11,477 reviews
Alaska Airlines
8.0
Very good
11,477 reviews

Crew

8.5

Boarding

8.1

Food

7.1

Overall

8.0

Entertainment

7.0

Comfort

7.8

Reviews

1 / 20
2.0
Mediocre

Art,Dec 2025

SAN - OGG

It was a five hour flight and my seat did not recline. I have had three back surgeries and I’m solid bone for my L3 vertebrae all the way to my tailbone. My body has never hurt so much. There was no TV on this flight and only a small can of soda was free.
Delta
7.9
Good
8,005 reviews
Alaska Airlines
8.0
Very good
11,477 reviews

Crew

8.5

Boarding

8.1

Food

7.1

Overall

8.0

Entertainment

7.0

Comfort

7.8

Reviews

1 / 20
2.0
Mediocre

Art,Dec 2025

SAN - OGG

It was a five hour flight and my seat did not recline. I have had three back surgeries and I’m solid bone for my L3 vertebrae all the way to my tailbone. My body has never hurt so much. There was no TV on this flight and only a small can of soda was free.
Hawaiian Airlines
7.8
Good
2,820 reviews
Alaska Airlines
8.0
Very good
11,477 reviews

Crew

8.5

Boarding

8.1

Food

7.1

Overall

8.0

Entertainment

7.0

Comfort

7.8

Reviews

1 / 20
2.0
Mediocre

Art,Dec 2025

SAN - OGG

It was a five hour flight and my seat did not recline. I have had three back surgeries and I’m solid bone for my L3 vertebrae all the way to my tailbone. My body has never hurt so much. There was no TV on this flight and only a small can of soda was free.
United Airlines
7.4
Good
9,091 reviews
Alaska Airlines
8.0
Very good
11,477 reviews

Crew

8.5

Boarding

8.1

Food

7.1

Overall

8.0

Entertainment

7.0

Comfort

7.8

Reviews

1 / 20
2.0
Mediocre

Art,Dec 2025

SAN - OGG

It was a five hour flight and my seat did not recline. I have had three back surgeries and I’m solid bone for my L3 vertebrae all the way to my tailbone. My body has never hurt so much. There was no TV on this flight and only a small can of soda was free.
American Airlines
7.2
Good
11,054 reviews
Alaska Airlines
8.0
Very good
11,477 reviews

Crew

8.5

Boarding

8.1

Food

7.1

Overall

8.0

Entertainment

7.0

Comfort

7.8

Reviews

1 / 20
2.0
Mediocre

Art,Dec 2025

SAN - OGG

It was a five hour flight and my seat did not recline. I have had three back surgeries and I’m solid bone for my L3 vertebrae all the way to my tailbone. My body has never hurt so much. There was no TV on this flight and only a small can of soda was free.

Related info for your journey

Find useful and relevant information for your journey from Chicago to Alaska. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • How long is the flight from Chicago to Alaska?

    For as low as $358, Alaska Airlines can have you in Alaska from Chicago in 15h 09m. Airlines will cover a distance of 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 to fly from Chicago to Alaska one-way?

    One-way options have recently been found by users for as low as $98 on Spirit Airlines. Other airlines that offer cheap prices include American Airlines from $164 and United Airlines from $195 one-way.

  • What are the most popular routes from Chicago to Alaska?

    When deciding which route to take from Chicago to Alaska consider Chicago O'Hare Intl - Anchorage, Chicago Midway - Anchorage or Chicago O'Hare Intl - Fairbanks as they are the most popular.

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

    Before booking your flight to Alaska from Chicago, check out the most reliable airlines to get you to your destination on time: Air Canada (76%), United Airlines (76%), Lufthansa( 76%).

  • What are the cheapest flights from Chicago to Alaska?

    Looking at all options, your cheapest flight can be booked for $210. While the most popular route (Chicago O'Hare Intl - Anchorage) can be booked for $349 on average, our data indicates $519 when flying from Chicago to Alaska.

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

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

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

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

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

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

    Currently, May is the cheapest month in which you can book a flight from Chicago to Alaska (average of $198). Flying from Chicago to Alaska in July is currently the most expensive (average of $450). 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.

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Alternative routes for Chicago to Alaska

See prices for flight routes from nearby airports that may be better suited for you.
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Top 5 airlines flying from Chicago to Alaska

Discover the top 5 airlines that operate flights from Chicago to Alaska. 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 December 18, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$209Average$516FlexibilityNo cancel feeOn-timeN/A
Hawaiian AirlinesCheapest$227Average$526FlexibilityNo cancel feeOn-time85%
American AirlinesCheapest$318Average$617FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$318Average$724FlexibilityNo cancel feeOn-time69%
Alaska AirlinesCheapest$356Average$657FlexibilityNo cancel feeOn-time75%

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