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$160+ 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 8/25. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — ANC
Aug 4 — Aug 111
Mon 8/4
Mon 8/11
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 July 30, 2025.

Round-trip from

$319
(American Airlines)

One-way from

$160
(Alaska Airlines)

Popular in

December

Cheapest in

October

Average price

$552

Good round-trip deal

$389 or less

Good one-way deal

$209 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. 1% potential increase in price ($9 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($16 potential savings vs. average RT price).
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Average for round-trip flights in July 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 July 30, 2025.

This Kiwi.com deal was found by Cheapflights users on 7/30. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/218:40 amORD - ANC
Nonstop6h 41mHawaiian Airlines
Wed 8/2711:25 pmANC - ORD
Nonstop6h 15mHawaiian Airlines
Deal found 7/30$320
This Alaska Airlines deal was found by Cheapflights users on 7/28. 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 8/272:07 pmORD - ANC
1 stop9h 33mAlaska Airlines
Sun 9/711:25 pmANC - ORD
Nonstop6h 15mAlaska Airlines
Deal found 7/28$328
This Delta deal was found by Cheapflights users on 7/29. 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 8/217:15 amORD - ANC
1 stop16h 40mDelta
Tue 8/2612:55 amANC - ORD
1 stop9h 22mDelta
Deal found 7/29$336
This United Airlines deal was found by Cheapflights users on 7/28. 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.
Mon 9/14:00 pmORD - ANC
Nonstop6h 47mUnited Airlines
Sat 9/611:59 pmANC - ORD
Nonstop6h 09mUnited Airlines
Deal found 7/28$337
This Delta deal was found by Cheapflights users on 7/29. 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 10/157:10 pmMDW - ANC
1 stop8h 41mDelta
Fri 10/176:05 amANC - MDW
1 stop8h 38mDelta
Deal found 7/29$338
This American Airlines deal was found by Cheapflights users on 7/29. 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 9/178:25 amORD - ANC
1 stop13h 42mAmerican Airlines
Sat 9/209:53 pmANC - ORD
Nonstop6h 24mAmerican Airlines
Deal found 7/29$342
This Hawaiian Airlines deal was found by Cheapflights users on 7/28. 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.
Wed 10/88:00 amORD - FAI
1 stop9h 56mHawaiian Airlines
Wed 10/1512:13 pmFAI - ORD
1 stop8h 46mHawaiian Airlines
Deal found 7/28$433
This Delta deal was found by Cheapflights users on 7/29. 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 10/117:37 amORD - FAI
1 stop20h 16mDelta
Tue 10/141:53 amFAI - ORD
1 stop18h 57mDelta
Deal found 7/29$434
This Alaska Airlines deal was found by Cheapflights users on 7/29. 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 8/276:20 amORD - FAI
1 stop19h 27mAlaska Airlines
Sat 8/302:08 amFAI - ORD
1 stop18h 51mAlaska Airlines
Deal found 7/29$469
This Delta deal was found by Cheapflights users on 7/29. 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 8/271:08 pmMDW - FAI
2 stops14h 42mDelta
Sun 8/3110:07 pmFAI - MDW
1 stop7h 43mDelta
Deal found 7/29$482
This Alaska Airlines deal was found by Cheapflights users on 7/29. 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 10/18:00 amORD - JNU
2 stops16h 29mAlaska Airlines
Sat 10/49:29 amJNU - ORD
1 stop20h 11mAlaska Airlines
Deal found 7/29$489
This Delta deal was found by Cheapflights users on 7/28. 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 9/107:15 amORD - JNU
1 stop13h 56mDelta
Sat 9/137:05 amJNU - ORD
1 stop13h 54mDelta
Deal found 7/28$501

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 July 30, 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

Thu 8/21

8:40 am-12:21 pm

Nonstop6h 41m

Anchorage

Wed 8/27

11:25 pm-8:40 am

Nonstop6h 15m

$320

ChicagoAnchorage

ORD - ANC

ORDANC

Chicago O'Hare Intl

Wed 8/27

2:07 pm-8:40 pm

1 stop9h 33m

Anchorage

Sun 9/7

11:25 pm-8:40 am

Nonstop6h 15m

$328

ChicagoAnchorage

ORD - ANC

ORDANC

Chicago O'Hare Intl

Thu 8/21

7:15 am-8:55 pm

1 stop16h 40m

Anchorage

Tue 8/26

12:55 am-1:17 pm

1 stop9h 22m

$336

ChicagoAnchorage

ORD - ANC

ORDANC

Chicago O'Hare Intl

Mon 9/1

4:00 pm-7:47 pm

Nonstop6h 47m

Anchorage

Sat 9/6

11:59 pm-9:08 am

Nonstop6h 09m

$337

ChicagoAnchorage

MDW - ANC

MDWANC

Chicago Midway

Wed 10/15

7:10 pm-12:51 am

1 stop8h 41m

Anchorage

Fri 10/17

6:05 am-5:43 pm

1 stop8h 38m

$338

ChicagoAnchorage

ORD - ANC

ORDANC

Chicago O'Hare Intl

Wed 9/17

8:25 am-7:07 pm

1 stop13h 42m

Anchorage

Sat 9/20

9:53 pm-7:17 am

Nonstop6h 24m

$342

ChicagoFairbanks

ORD - FAI

ORDFAI

Chicago O'Hare Intl

Wed 10/8

8:00 am-2:56 pm

1 stop9h 56m

Fairbanks

Wed 10/15

12:13 pm-11:59 pm

1 stop8h 46m

$433

ChicagoFairbanks

ORD - FAI

ORDFAI

Chicago O'Hare Intl

Sat 10/11

7:37 am-12:53 am

1 stop20h 16m

Fairbanks

Tue 10/14

1:53 am-11:50 pm

1 stop18h 57m

$434

ChicagoFairbanks

ORD - FAI

ORDFAI

Chicago O'Hare Intl

Wed 8/27

6:20 am-10:47 pm

1 stop19h 27m

Fairbanks

Sat 8/30

2:08 am-11:59 pm

1 stop18h 51m

$469

ChicagoFairbanks

MDW - FAI

MDWFAI

Chicago Midway

Wed 8/27

1:08 pm-12:50 am

2 stops14h 42m

Fairbanks

Sun 8/31

10:07 pm-8:50 am

1 stop7h 43m

$482

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/28

Showing 1-10 of 40 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 $645). 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 July 30, 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 July 30, 2025.

The most flights from CHI to USAK are scheduled on a Monday (12 on average). You will have fewer flight options on Sunday, which is when the least amount of flights are scheduled (6 on average).

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 July 30, 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

Overall

8.0

Crew

8.5

Food

7.1

Boarding

8.1

Comfort

7.8

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

Jonathan,Jul 2025

SEA - BOS

Fantastic Check-in with easy baggage drop. While it took a while to find out which was the gate, the boarding was a dream, the stewards were simply incredible and the flight fantastic.
Alaska Airlines
8.0
Very good
10,000 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Overall

8.0

Crew

8.5

Food

7.1

Boarding

8.1

Comfort

7.8

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

Jonathan,Jul 2025

SEA - BOS

Fantastic Check-in with easy baggage drop. While it took a while to find out which was the gate, the boarding was a dream, the stewards were simply incredible and the flight fantastic.
Delta
8.0
Very good
7,980 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Overall

8.0

Crew

8.5

Food

7.1

Boarding

8.1

Comfort

7.8

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

Jonathan,Jul 2025

SEA - BOS

Fantastic Check-in with easy baggage drop. While it took a while to find out which was the gate, the boarding was a dream, the stewards were simply incredible and the flight fantastic.
Hawaiian Airlines
7.8
Good
2,611 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Overall

8.0

Crew

8.5

Food

7.1

Boarding

8.1

Comfort

7.8

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

Jonathan,Jul 2025

SEA - BOS

Fantastic Check-in with easy baggage drop. While it took a while to find out which was the gate, the boarding was a dream, the stewards were simply incredible and the flight fantastic.
United Airlines
7.4
Good
8,896 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Overall

8.0

Crew

8.5

Food

7.1

Boarding

8.1

Comfort

7.8

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

Jonathan,Jul 2025

SEA - BOS

Fantastic Check-in with easy baggage drop. While it took a while to find out which was the gate, the boarding was a dream, the stewards were simply incredible and the flight fantastic.
American Airlines
7.2
Good
10,000 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Overall

8.0

Crew

8.5

Food

7.1

Boarding

8.1

Comfort

7.8

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

Jonathan,Jul 2025

SEA - BOS

Fantastic Check-in with easy baggage drop. While it took a while to find out which was the gate, the boarding was a dream, the stewards were simply incredible and the flight fantastic.

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.

  • 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 $160 on Alaska Airlines. Other airlines that offer cheap prices include Delta from $170 and United Airlines from $200 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 O'Hare Intl - Fairbanks or Chicago Midway - Anchorage 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: United Airlines (92%), Air Canada (88%), Lufthansa( 88%).

  • 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 $407 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 $645). 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 July 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$198Average$550FlexibilityNo cancel feeOn-timeN/A
Hawaiian AirlinesCheapest$227Average$562FlexibilityNo cancel feeOn-time85%
American AirlinesCheapest$318Average$623FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$344Average$710FlexibilityNo cancel feeOn-time69%
Alaska AirlinesCheapest$366Average$648FlexibilityNo cancel feeOn-time75%

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