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$142+ 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 11/18. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — ANC
Aug 26 — Sep 21
Tue 8/26
Tue 9/2
1 adult, Economy
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Cheap flight deals from Chicago to Alaska

Keep the following information in mind while searching for Chicago to Alaska flight deals. Data was last updated August 21, 2025.

Round-trip from

$318
(Delta)

One-way from

$142
(Delta)

Popular in

December

Cheapest in

April

Average price

$541

Good round-trip deal

$318 or less

Good one-way deal

$189 or less
From Chicago (CHI) to Alaska
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One-way flight from Chicago (CHI) to Alaska
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Highest demand for flights based on searches. 0% potential increase in price ($4 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($14 potential savings vs. average RT price).
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Average for round-trip flights in August 2025
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Price to beat on a round-trip flight from Chicago (CHI) to Alaska.
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Price to beat on a one-way flight from Chicago (CHI) to Alaska.
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Find 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 August 21, 2025.

This Hawaiian Airlines deal was found by Cheapflights users on 8/21. 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 Hawaiian Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/198:40 amORD - ANC
Nonstop6h 41mHawaiian Airlines
Thu 9/2511:25 pmANC - ORD
Nonstop6h 15mHawaiian Airlines
Deal found 8/21$318
This American Airlines deal was found by Cheapflights users on 8/19. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/175:01 pmORD - ANC
Nonstop6h 47mAmerican Airlines
Sat 9/209:53 pmANC - ORD
Nonstop6h 24mAmerican Airlines
Deal found 8/19$319
This Delta deal was found by Cheapflights users on 8/19. 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.
Wed 10/152:10 pmORD - ANC
2 stops11h 33mDelta
Sat 10/256:05 amANC - ORD
1 stop12h 14mDelta
Deal found 8/19$323
This Delta deal was found by Cheapflights users on 8/19. 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.
Wed 9/178:52 amORD - ANC
1 stop13h 01mDelta
Fri 9/1912:55 amANC - ORD
2 stops12h 25mDelta
Deal found 8/19$325
This Alaska Airlines deal was found by Cheapflights users on 8/21. 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.
Fri 9/196:20 amORD - ANC
1 stop11h 39mAlaska Airlines
Thu 9/2511:25 pmANC - ORD
Nonstop6h 15mAlaska Airlines
Deal found 8/21$328
This Delta deal was found by Cheapflights users on 8/18. 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 10/48:50 amORD - ANC
1 stop13h 03mDelta
Sat 10/116:00 amANC - ORD
1 stop8h 18mDelta
Deal found 8/18$331
This American Airlines deal was found by Cheapflights users on 8/21. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/2110:03 amORD - ANC
1 stop12h 05mAmerican Airlines
Sun 9/289:53 pmANC - ORD
Nonstop6h 24mAmerican Airlines
Deal found 8/21$337
This Delta deal was found by Cheapflights users on 8/21. 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 9/196:10 pmORD - ANC
1 stop10h 27mDelta
Wed 9/2412:55 amANC - ORD
1 stop9h 25mDelta
Deal found 8/21$338
This Delta deal was found by Cheapflights users on 8/21. 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 9/201:43 pmMDW - ANC
1 stop8h 10mDelta
Sat 9/276:15 amANC - MDW
1 stop8h 20mDelta
Deal found 8/21$338
This Alaska Airlines deal was found by Cheapflights users on 8/19. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/158:40 amORD - ANC
Nonstop6h 41mAlaska Airlines
Mon 9/2211:00 amANC - ORD
1 stop10h 03mAlaska Airlines
Deal found 8/19$342
This Delta deal was found by Cheapflights users on 8/21. 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 9/1112:59 pmORD - ANC
1 stop10h 20mDelta
Tue 9/166:00 amANC - ORD
2 stops12h 57mDelta
Deal found 8/21$344
This Delta deal was found by Cheapflights users on 8/21. 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 9/197:15 pmMDW - ANC
1 stop9h 21mDelta
Mon 9/225:15 pmANC - MDW
2 stops12h 38mDelta
Deal found 8/21$344

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 August 21, 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

Fri 9/19

9:20 am-1:09 pm

Nonstop6h 49m

Anchorage

Sun 9/21

8:49 pm-5:58 am

Nonstop6h 09m

$318

ChicagoAnchorage

ORD - ANC

ORDANC

Chicago O'Hare Intl

Fri 10/3

8:40 am-12:21 pm

Nonstop6h 41m

Anchorage

Sat 10/11

11:11 pm-8:40 am

Nonstop6h 29m

$318

ChicagoAnchorage

ORD - ANC

ORDANC

Chicago O'Hare Intl

Sat 10/4

8:10 am-12:08 pm

Nonstop6h 58m

Anchorage

Sat 10/11

11:11 pm-8:40 am

Nonstop6h 29m

$318

ChicagoAnchorage

ORD - ANC

ORDANC

Chicago O'Hare Intl

Wed 9/17

8:52 am-6:53 pm

1 stop13h 01m

Anchorage

Sat 9/20

6:00 am-11:59 pm

1 stop14h 59m

$318

ChicagoAnchorage

ORD - ANC

ORDANC

Chicago O'Hare Intl

Tue 9/16

4:00 pm-7:47 pm

Nonstop6h 47m

Anchorage

Tue 9/23

8:49 pm-5:58 am

Nonstop6h 09m

$318

ChicagoAnchorage

ORD - ANC

ORDANC

Chicago O'Hare Intl

Mon 9/15

8:40 am-12:21 pm

Nonstop6h 41m

Anchorage

Fri 9/19

11:25 pm-8:40 am

Nonstop6h 15m

$318

ChicagoAnchorage

ORD - ANC

ORDANC

Chicago O'Hare Intl

Wed 10/22

6:08 am-6:31 pm

1 stop15h 23m

Anchorage

Fri 10/24

12:30 am-3:00 pm

2 stops11h 30m

$318

ChicagoAnchorage

ORD - ANC

ORDANC

Chicago O'Hare Intl

Wed 9/17

8:52 am-6:53 pm

1 stop13h 01m

Anchorage

Sun 9/21

12:55 am-6:30 pm

2 stops14h 35m

$318

ChicagoAnchorage

MDW - ANC

MDWANC

Chicago Midway

Sat 10/4

7:15 pm-1:36 am

1 stop9h 21m

Anchorage

Sat 10/11

6:05 am-5:43 pm

1 stop8h 38m

$338

ChicagoAnchorage

MDW - ANC

MDWANC

Chicago Midway

Wed 10/15

7:10 pm-12:51 am

1 stop8h 41m

Anchorage

Sat 10/25

8:15 pm-11:53 am

1 stop12h 38m

$338

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/19

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, January is the cheapest month in which you can book a flight from Chicago to Alaska (average of $456). Flying from Chicago to Alaska in July is currently the most expensive (average of $643). 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 August 21, 2025.

When flying from Chicago to Alaska, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

Weekly flight availability from Chicago to Alaska

Explore weekly flight availability from Chicago to Alaska. 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 August 21, 2025.

The most flights from CHI to USAK are scheduled on a Wednesday (12 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (7 on average).

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 August 21, 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
10,000 reviews

Entertainment

7.0

Comfort

7.8

Food

7.1

Boarding

8.1

Crew

8.5

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Anonymous,Aug 2025

PDX - SJC

They had no snacks and had to pay for the Wifi.
Alaska Airlines
8.0
Very good
10,000 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Entertainment

7.0

Comfort

7.8

Food

7.1

Boarding

8.1

Crew

8.5

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Anonymous,Aug 2025

PDX - SJC

They had no snacks and had to pay for the Wifi.
Delta
8.0
Very good
7,981 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Entertainment

7.0

Comfort

7.8

Food

7.1

Boarding

8.1

Crew

8.5

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Anonymous,Aug 2025

PDX - SJC

They had no snacks and had to pay for the Wifi.
Hawaiian Airlines
7.8
Good
2,672 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Entertainment

7.0

Comfort

7.8

Food

7.1

Boarding

8.1

Crew

8.5

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Anonymous,Aug 2025

PDX - SJC

They had no snacks and had to pay for the Wifi.
United Airlines
7.4
Good
8,930 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Entertainment

7.0

Comfort

7.8

Food

7.1

Boarding

8.1

Crew

8.5

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Anonymous,Aug 2025

PDX - SJC

They had no snacks and had to pay for the Wifi.
American Airlines
7.2
Good
10,000 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Entertainment

7.0

Comfort

7.8

Food

7.1

Boarding

8.1

Crew

8.5

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Anonymous,Aug 2025

PDX - SJC

They had no snacks and had to pay for the Wifi.

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 $318, United Airlines can have you in Alaska from Chicago in 6h 41m. Airlines will cover a distance of 2837 mi. Most flights are nonstop.

  • 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 $142 on Delta. Other airlines that offer cheap prices include Alaska Airlines from $160 and Hawaiian Airlines from $160 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: Atlas Air (100%), United Airlines (80%), Alaska Airlines( 80%).

  • What are the cheapest flights from Chicago to Alaska?

    Looking at all options, your cheapest flight can be booked for $160. While the most popular route (Chicago O'Hare Intl - Anchorage) can be booked for $311 on average our data indicates $451 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, January is the cheapest month in which you can book a flight from Chicago to Alaska (average of $456). Flying from Chicago to Alaska in July is currently the most expensive (average of $643). 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

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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 August 21, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$198Average$552FlexibilityNo cancel feeOn-timeN/A
Hawaiian AirlinesCheapest$237Average$526FlexibilityNo cancel feeOn-time85%
American AirlinesCheapest$318Average$620FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$342Average$704FlexibilityNo cancel feeOn-time69%
Alaska AirlinesCheapest$362Average$647FlexibilityNo cancel feeOn-time75%

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