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$155+ 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 10/11. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — ANC
Oct 11 — Oct 181
Sat 10/11
Sat 10/18
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 September 11, 2025.

Round-trip from

$318
(United Airlines)

One-way from

$155
(KAYAK)

Popular in

December

Cheapest in

April

Average price

$456

Good round-trip deal

$318 or less

Good one-way deal

$250 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 ($5 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 September 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 September 11, 2025.

This Alaska Airlines deal was found by Cheapflights users on 9/10. 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 10/48:20 amORD - ANC
Nonstop6h 58mAlaska Airlines
Sat 10/1111:11 pmANC - ORD
Nonstop6h 29mAlaska Airlines
Deal found 9/10$318
This American Airlines deal was found by Cheapflights users on 9/10. 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 10/15:01 pmORD - ANC
Nonstop6h 47mAmerican Airlines
Sat 10/49:53 pmANC - ORD
Nonstop6h 24mAmerican Airlines
Deal found 9/10$319
This Trip.com deal was found by Cheapflights users on 9/10. 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.
Fri 10/179:20 amORD - ANC
Nonstop6h 58mHawaiian Airlines
Sun 10/194:00 pmANC - ORD
1 stop10h 01mHawaiian Airlines
Deal found 9/10$320
This lastminute.com deal was found by Cheapflights users on 9/10. 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 lastminute.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/152:05 pmORD - ANC
2 stops11h 43mAlaska Airlines
Tue 12/98:05 amANC - ORD
2 stops12h 45mAlaska Airlines
Deal found 9/10$321
This Trip.com deal was found by Cheapflights users on 9/10. 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.
Thu 11/206:00 amORD - ANC
1 stop9h 46mMultiple Airlines
Sun 11/2312:08 pmANC - ORD
1 stop13h 53mMultiple Airlines
Deal found 9/10$324
This Hawaiian Airlines deal was found by Cheapflights users on 9/10. 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.
Sat 10/47:00 amORD - ANC
1 stop9h 22mHawaiian Airlines
Sat 10/1111:11 pmANC - ORD
Nonstop6h 29mHawaiian Airlines
Deal found 9/10$328
This Trip.com deal was found by Cheapflights users on 9/10. 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.
Wed 11/59:20 amORD - ANC
2 stops16h 28mMultiple Airlines
Wed 11/129:05 amANC - ORD
1 stop9h 35mMultiple Airlines
Deal found 9/10$329
This Alaska Airlines deal was found by Cheapflights users on 9/10. 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 10/313:25 pmORD - ANC
1 stop10h 23mAlaska Airlines
Sat 11/15:05 amANC - ORD
1 stop13h 35mAlaska Airlines
Deal found 9/10$332
This Delta deal was found by Cheapflights users on 9/9. 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 11/117:02 pmMDW - ANC
1 stop8h 54mDelta
Wed 11/126:05 amANC - MDW
1 stop9h 13mDelta
Deal found 9/9$332
This Alaska Airlines deal was found by Cheapflights users on 9/10. 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 10/38:40 amORD - ANC
Nonstop6h 41mAlaska Airlines
Mon 10/69:00 amANC - ORD
1 stop18h 24mAlaska Airlines
Deal found 9/10$337
This Alaska Airlines deal was found by Cheapflights users on 9/10. 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 12/118:00 amORD - ANC
1 stop19h 48mAlaska Airlines
Thu 1/19:05 amANC - ORD
1 stop16h 57mAlaska Airlines
Deal found 9/10$338
This Delta deal was found by Cheapflights users on 9/9. 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 11/87:10 pmMDW - ANC
1 stop8h 41mDelta
Wed 11/126:05 amANC - MDW
1 stop9h 13mDelta
Deal found 9/9$338

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 September 11, 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

Tue 10/7

4:10 pm-7:57 pm

Nonstop6h 47m

Anchorage

Tue 10/14

9:04 pm-6:13 am

Nonstop6h 09m

$318

ChicagoAnchorage

ORD - ANC

ORDANC

Chicago O'Hare Intl

Sat 10/4

4:10 pm-7:57 pm

Nonstop6h 47m

Anchorage

Sat 10/11

9:04 pm-6:13 am

Nonstop6h 09m

$318

ChicagoAnchorage

ORD - ANC

ORDANC

Chicago O'Hare Intl

Thu 10/2

4:10 pm-7:57 pm

Nonstop6h 47m

Anchorage

Wed 10/8

9:04 pm-6:13 am

Nonstop6h 09m

$318

ChicagoAnchorage

ORD - ANC

ORDANC

Chicago O'Hare Intl

Sat 10/4

6:00 am-12:18 pm

1 stop9h 18m

Anchorage

Sat 10/11

11:11 pm-8:40 am

Nonstop6h 29m

$328

ChicagoAnchorage

ORD - ANC

ORDANC

Chicago O'Hare Intl

Wed 10/22

6:00 am-9:45 pm

1 stop18h 45m

Anchorage

Sat 10/25

11:11 pm-8:40 am

Nonstop6h 29m

$328

ChicagoAnchorage

ORD - ANC

ORDANC

Chicago O'Hare Intl

Fri 10/3

8:40 am-12:21 pm

Nonstop6h 41m

Anchorage

Mon 10/6

9:00 am-6:24 am

1 stop18h 24m

$337

ChicagoAnchorage

ORD - ANC

ORDANC

Chicago O'Hare Intl

Thu 10/9

6:05 pm-1:59 am

1 stop10h 54m

Anchorage

Thu 10/16

11:15 am-11:50 pm

1 stop9h 35m

$338

ChicagoAnchorage

ORD - ANC

ORDANC

Chicago O'Hare Intl

Wed 10/15

2:25 pm-1:59 am

1 stop14h 34m

Anchorage

Fri 10/24

12:30 am-5:18 pm

1 stop13h 48m

$338

ChicagoAnchorage

ORD - ANC

ORDANC

Chicago O'Hare Intl

Wed 10/8

7:37 am-4:22 pm

1 stop11h 45m

Anchorage

Tue 10/14

12:30 am-1:30 pm

1 stop10h 00m

$338

ChicagoAnchorage

MDW - ANC

MDWANC

Chicago Midway

Sat 10/4

11:00 am-6:56 pm

1 stop10h 56m

Anchorage

Sat 10/11

6:05 am-5:43 pm

1 stop8h 38m

$338

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/10

Showing 1-10 of 59 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 $642). 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 September 11, 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 September 11, 2025.

The most flights from CHI to USAK are scheduled on a Monday (7 on average). You will have fewer flight options on Monday, 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 September 11, 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

Crew

8.5

Boarding

8.1

Comfort

7.8

Overall

8.0

Food

7.1

Reviews

1 / 20
6.0
Good

Hannah,Aug 2025

SFO - SAN

Ticket said TSA pre check, but then the TSA agent said that Alaska Airlines has not actually entered the pre check information for the ticket, so I had to use regular security. During boarding, I have a disability and need to board early. The Alaska Airlines employee announced disability boarding, but then immediately announced 2 other groups to board, so I still had to fight the crowds. On the plane, the stewardess was brusk and rude. Seats were very uncomfortable, especially on lower back.
Alaska Airlines
8.0
Very good
10,000 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Entertainment

7.0

Crew

8.5

Boarding

8.1

Comfort

7.8

Overall

8.0

Food

7.1

Reviews

1 / 20
6.0
Good

Hannah,Aug 2025

SFO - SAN

Ticket said TSA pre check, but then the TSA agent said that Alaska Airlines has not actually entered the pre check information for the ticket, so I had to use regular security. During boarding, I have a disability and need to board early. The Alaska Airlines employee announced disability boarding, but then immediately announced 2 other groups to board, so I still had to fight the crowds. On the plane, the stewardess was brusk and rude. Seats were very uncomfortable, especially on lower back.
Delta
8.0
Very good
7,960 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Entertainment

7.0

Crew

8.5

Boarding

8.1

Comfort

7.8

Overall

8.0

Food

7.1

Reviews

1 / 20
6.0
Good

Hannah,Aug 2025

SFO - SAN

Ticket said TSA pre check, but then the TSA agent said that Alaska Airlines has not actually entered the pre check information for the ticket, so I had to use regular security. During boarding, I have a disability and need to board early. The Alaska Airlines employee announced disability boarding, but then immediately announced 2 other groups to board, so I still had to fight the crowds. On the plane, the stewardess was brusk and rude. Seats were very uncomfortable, especially on lower back.
Hawaiian Airlines
7.8
Good
2,723 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Entertainment

7.0

Crew

8.5

Boarding

8.1

Comfort

7.8

Overall

8.0

Food

7.1

Reviews

1 / 20
6.0
Good

Hannah,Aug 2025

SFO - SAN

Ticket said TSA pre check, but then the TSA agent said that Alaska Airlines has not actually entered the pre check information for the ticket, so I had to use regular security. During boarding, I have a disability and need to board early. The Alaska Airlines employee announced disability boarding, but then immediately announced 2 other groups to board, so I still had to fight the crowds. On the plane, the stewardess was brusk and rude. Seats were very uncomfortable, especially on lower back.
United Airlines
7.4
Good
8,937 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Entertainment

7.0

Crew

8.5

Boarding

8.1

Comfort

7.8

Overall

8.0

Food

7.1

Reviews

1 / 20
6.0
Good

Hannah,Aug 2025

SFO - SAN

Ticket said TSA pre check, but then the TSA agent said that Alaska Airlines has not actually entered the pre check information for the ticket, so I had to use regular security. During boarding, I have a disability and need to board early. The Alaska Airlines employee announced disability boarding, but then immediately announced 2 other groups to board, so I still had to fight the crowds. On the plane, the stewardess was brusk and rude. Seats were very uncomfortable, especially on lower back.
American Airlines
7.2
Good
10,000 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Entertainment

7.0

Crew

8.5

Boarding

8.1

Comfort

7.8

Overall

8.0

Food

7.1

Reviews

1 / 20
6.0
Good

Hannah,Aug 2025

SFO - SAN

Ticket said TSA pre check, but then the TSA agent said that Alaska Airlines has not actually entered the pre check information for the ticket, so I had to use regular security. During boarding, I have a disability and need to board early. The Alaska Airlines employee announced disability boarding, but then immediately announced 2 other groups to board, so I still had to fight the crowds. On the plane, the stewardess was brusk and rude. Seats were very uncomfortable, especially on lower back.

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 47m. 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 $160 on Alaska Airlines. Other airlines that offer cheap prices include Hawaiian Airlines from $160 and United 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 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: Atlas Air (100%), Alaska Airlines (80%), Hawaiian Airlines( 78%).

  • 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 $318 on average, our data indicates $676 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 $642). 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 September 11, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$198Average$549FlexibilityNo cancel feeOn-timeN/A
Hawaiian AirlinesCheapest$237Average$526FlexibilityNo cancel feeOn-time85%
American AirlinesCheapest$318Average$600FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$336Average$704FlexibilityNo cancel feeOn-time69%
Alaska AirlinesCheapest$365Average$686FlexibilityNo cancel feeOn-time75%

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