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$149+ Cheap flights from Alaska to Chicago (CHI)

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 11/15. Fares are subject to change and may not be available on all flights or dates of travel.
ANC — CHI
ago. 25 — sep. 11
lun. 8/25
lun. 9/1
1 adult, Economy
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Cheap flight deals from Alaska to Chicago

Keep the following information in mind while searching for Alaska to Chicago flight deals. Data was last updated agosto 20, 2025.

Round-trip from

$311
(Delta)

One-way from

$149
(Delta)

Popular in

March

Cheapest in

November

Average price

$424

Good round-trip deal

$484 or less

Good one-way deal

$319 or less
From Alaska to Chicago (CHI)
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One-way flight from Alaska to Chicago (CHI)
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Highest demand for flights based on searches. 16% potential increase in price ($100 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($16 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 Alaska to Chicago (CHI).
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Price to beat on a one-way flight from Alaska to Chicago (CHI).
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Find flight deals from Alaska to Chicago

Cheapest flights from Alaska to Chicago
Explore the most affordable flight options available from Alaska to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on agosto 20, 2025.

This Hawaiian Airlines 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 Hawaiian Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 10/1011:11 pmANC - ORD
Nonstop6h 29mHawaiian Airlines
sáb. 10/188:10 amORD - ANC
Nonstop6h 58mHawaiian Airlines
Deal found 8/18$318
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.
mié. 11/56:05 amANC - MDW
1 stop8h 38mDelta
sáb. 11/83:00 pmMDW - ANC
1 stop12h 51mDelta
Deal found 8/19$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.
jue. 9/259:53 pmANC - ORD
Nonstop6h 24mAmerican Airlines
lun. 9/295:01 pmORD - ANC
Nonstop6h 47mAmerican 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.
mar. 11/412:30 amANC - ORD
2 stops11h 25mDelta
sáb. 11/86:08 amORD - ANC
1 stop15h 23mDelta
Deal found 8/19$323
This American Airlines deal was found by Cheapflights users on 8/20. 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.
jue. 9/259:53 pmANC - ORD
Nonstop6h 24mAmerican Airlines
mar. 9/305:01 pmORD - ANC
Nonstop6h 47mAmerican Airlines
Deal found 8/20$324
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.
vie. 9/269:53 pmANC - ORD
Nonstop6h 24mAmerican Airlines
sáb. 10/45:01 pmORD - ANC
Nonstop6h 47mAmerican Airlines
Deal found 8/19$326
This Hawaiian Airlines 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 Hawaiian Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 10/211:25 pmANC - ORD
Nonstop6h 15mHawaiian Airlines
sáb. 10/47:00 amORD - ANC
1 stop9h 22mHawaiian Airlines
Deal found 8/18$328
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.
jue. 9/2512:55 amANC - ORD
1 stop9h 25mDelta
sáb. 10/48:50 amORD - ANC
1 stop13h 03mDelta
Deal found 8/19$331
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.
vie. 9/2610:00 pmANC - MDW
1 stop7h 53mDelta
sáb. 10/49:20 amMDW - ANC
1 stop12h 33mDelta
Deal found 8/19$331
This Alaska Airlines 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 10/1011:11 pmANC - ORD
Nonstop6h 29mAlaska Airlines
sáb. 10/187:00 amORD - ANC
2 stops14h 46mAlaska Airlines
Deal found 8/18$338
This Delta deal was found by Cheapflights users on 8/17. 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.
lun. 10/66:05 amANC - MDW
1 stop8h 38mDelta
sáb. 10/117:10 pmMDW - ANC
1 stop8h 41mDelta
Deal found 8/17$338
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.
vie. 10/1011:15 amANC - ORD
1 stop9h 35mDelta
sáb. 10/111:25 pmORD - ANC
2 stops12h 18mDelta
Deal found 8/19$343

Cheapflights Fare Finder

 
Customize your flight search to find flights from Alaska to Chicago 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 agosto 20, 2025.
Use the filters below to find and compare flights from Alaska to Chicago that are best for you.

Fly from

Alaska

Fly to

Chicago

Route

Depart

Return

Price

AnchorageChicago

ANC - ORD

ANCORD

Anchorage

mar. 1/13

9:55 pm-2:56 pm

1 stop14h 01m

Chicago O'Hare Intl

dom. 2/8

7:30 am-2:42 pm

1 stop10h 12m

$311

AnchorageChicago

ANC - ORD

ANCORD

Anchorage

vie. 10/10

11:11 pm-8:40 am

Nonstop6h 29m

Chicago O'Hare Intl

sáb. 10/18

8:10 am-12:08 pm

Nonstop6h 58m

$318

AnchorageChicago

ANC - ORD

ANCORD

Anchorage

jue. 10/2

11:25 pm-8:40 am

Nonstop6h 15m

Chicago O'Hare Intl

sáb. 10/4

8:10 am-12:08 pm

Nonstop6h 58m

$318

AnchorageChicago

ANC - ORD

ANCORD

Anchorage

mié. 11/5

11:15 am-11:50 pm

1 stop9h 35m

Chicago O'Hare Intl

sáb. 11/8

6:08 am-6:31 pm

1 stop15h 23m

$318

AnchorageChicago

ANC - ORD

ANCORD

Anchorage

vie. 10/10

11:11 pm-8:40 am

Nonstop6h 29m

Chicago O'Hare Intl

sáb. 10/18

8:10 am-12:08 pm

Nonstop6h 58m

$318

AnchorageChicago

ANC - ORD

ANCORD

Anchorage

jue. 10/2

11:25 pm-8:40 am

Nonstop6h 15m

Chicago O'Hare Intl

sáb. 10/11

8:10 am-12:08 pm

Nonstop6h 58m

$318

AnchorageChicago

ANC - ORD

ANCORD

Anchorage

vie. 10/10

11:15 am-11:50 pm

1 stop9h 35m

Chicago O'Hare Intl

sáb. 10/11

8:57 am-6:31 pm

1 stop12h 34m

$318

AnchorageChicago

ANC - MDW

ANCMDW

Anchorage

mié. 11/5

6:05 am-5:43 pm

1 stop8h 38m

Chicago Midway

sáb. 11/8

3:00 pm-12:51 am

1 stop12h 51m

$318

AnchorageChicago

ANC - MDW

ANCMDW

Anchorage

vie. 9/26

10:00 pm-8:53 am

1 stop7h 53m

Chicago Midway

sáb. 10/4

9:20 am-6:53 pm

1 stop12h 33m

$331

AnchorageChicago

ANC - MDW

ANCMDW

Anchorage

lun. 10/6

6:05 am-5:43 pm

1 stop8h 38m

Chicago Midway

sáb. 10/11

7:10 pm-12:51 am

1 stop8h 41m

$338

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/19

Showing 1-10 of 50 results
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Best time to book a flight from Alaska to Chicago

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

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

Currently, August is the cheapest month in which you can book a flight from Alaska to Chicago (average of $245). Flying from Alaska to Chicago in March is currently the most expensive (average of $321). 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 AK to CHI?

Find hourly flight availability from Alaska to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated agosto 20, 2025.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Alaska to Chicago as you normally would.

Weekly flight availability from Alaska to Chicago

Explore weekly flight availability from Alaska to Chicago. 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 agosto 20, 2025.

The most flights from USAK to CHI are scheduled on a Monday (9 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (6 on average).

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

Related info for your journey

Find useful and relevant information for your journey from Alaska to Chicago. 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 Alaska to Chicago?

    There are many flights that can get you from Alaska to Chicago in 6h 29m. Fly via Delta or Alaska Airlines to get the fastest option. Alaska and Chicago are separated by a distance of 2837 mi. This flight may include one or multiple stops.

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

    The cheapest airline one-way is Delta, with whom users have recently found tickets for as low as $149. However, be on the lookout for offers from United Airlines and American Airlines, as they are both options that can get you from Alaska to Chicago for a low price.

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

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

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

    Looking for the most reliable airlines to get you to your destination on time? Our data shows these are most likely to get you from Alaska to Chicago on time: United Airlines (79%), Air Canada (79%), Atlas Air (78%).

  • What are the cheapest flights from Alaska to Chicago?

    Looking for the cheapest flight from Alaska to Chicago? While on average our users pay $880, our data indicates the cheapest price to be $198. The most popular route (Anchorage - Chicago O'Hare Intl), is priced around $311.

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

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

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

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

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

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

    Currently, August is the cheapest month in which you can book a flight from Alaska to Chicago (average of $245). Flying from Alaska to Chicago in March is currently the most expensive (average of $321). 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 Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
Lansing
Hammond
Benton Harbor
Porter
Chesterton

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Alternative routes for Alaska to Chicago

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

Discover the top 5 airlines that operate flights from Alaska to Chicago. 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 agosto 20, 2025.
AirlineCheapestAverageFlexibilityOn-time
Hawaiian AirlinesCheapest$187Average$461FlexibilityNo cancel feeOn-time85%
DeltaCheapest$337Average$423FlexibilityNo cancel feeOn-timeN/A
Alaska AirlinesCheapest$337Average$673FlexibilityNo cancel feeOn-time75%
American AirlinesCheapest$338Average$574FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$345Average$499FlexibilityNo cancel feeOn-time69%

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