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$153+ 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 10/26. Fares are subject to change and may not be available on all flights or dates of travel.
ANC — CHI
Oct 15 — Oct 221
Wed 10/15
Wed 10/22
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 September 15, 2025.

Round-trip from

$318
(United Airlines)

One-way from

$153
(KAYAK)

Popular in

March

Cheapest in

November

Average price

$398

Good round-trip deal

$377 or less

Good one-way deal

$212 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 ($15 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 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 September 15, 2025.

This United Airlines deal was found by Cheapflights users on 9/14. 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.
Wed 10/159:04 pmANC - ORD
Nonstop6h 09mUnited Airlines
Mon 10/204:10 pmORD - ANC
Nonstop6h 47mUnited Airlines
Deal found 9/14$318
This United Airlines deal was found by Cheapflights users on 9/13. 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.
Thu 10/99:04 pmANC - ORD
Nonstop6h 09mUnited Airlines
Tue 10/142:53 pmORD - ANC
1 stop10h 49mUnited Airlines
Deal found 9/13$328
This Alaska Airlines deal was found by Cheapflights users on 9/13. 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 10/64:34 pmANC - ORD
1 stop10h 50mAlaska Airlines
Sat 10/118:20 amORD - ANC
Nonstop6h 58mAlaska Airlines
Deal found 9/13$337
This Alaska Airlines deal was found by Cheapflights users on 9/14. 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 10/2411:11 pmANC - ORD
Nonstop6h 29mAlaska Airlines
Fri 10/312:54 pmORD - ANC
2 stops23h 16mAlaska Airlines
Deal found 9/14$338
This Alaska Airlines deal was found by Cheapflights users on 9/13. 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.
Tue 11/45:35 pmANC - ORD
1 stop27h 49mAlaska Airlines
Mon 11/107:00 amORD - ANC
2 stops20h 49mAlaska Airlines
Deal found 9/13$346
This Alaska Airlines deal was found by Cheapflights users on 9/14. 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 11/171:04 amANC - ORD
1 stop17h 36mAlaska Airlines
Fri 11/286:00 amORD - ANC
1 stop16h 32mAlaska Airlines
Deal found 9/14$347
This Alaska Airlines deal was found by Cheapflights users on 9/14. 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 10/91:47 amANC - ORD
1 stop24h 14mAlaska Airlines
Sat 10/187:00 amORD - ANC
1 stop9h 22mAlaska Airlines
Deal found 9/14$350
This Delta deal was found by Cheapflights users on 9/14. 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 10/2112:30 amANC - ORD
1 stop10h 00mDelta
Wed 10/292:25 pmORD - ANC
1 stop11h 18mDelta
Deal found 9/14$356
This Delta deal was found by Cheapflights users on 9/13. 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 10/96:05 amANC - MDW
1 stop8h 38mDelta
Mon 10/137:10 pmMDW - ANC
1 stop8h 41mDelta
Deal found 9/13$356
This Delta deal was found by Cheapflights users on 9/14. 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 10/229:45 pmANC - MDW
1 stop8h 10mDelta
Wed 10/291:48 pmMDW - ANC
2 stops15h 11mDelta
Deal found 9/14$361
This Delta deal was found by Cheapflights users on 9/13. 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.
Mon 10/65:20 pmANC - MDW
2 stops12h 20mDelta
Sat 10/111:06 pmMDW - ANC
2 stops15h 53mDelta
Deal found 9/13$366
This Delta deal was found by Cheapflights users on 9/13. 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 11/146:05 amANC - MDW
1 stop9h 13mDelta
Sun 11/169:32 amMDW - ANC
2 stops16h 17mDelta
Deal found 9/13$392

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 September 15, 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

Fri 10/24

11:11 pm-8:40 am

Nonstop6h 29m

Chicago O'Hare Intl

Fri 10/31

6:00 am-2:14 pm

1 stop11h 14m

$328

AnchorageChicago

ANC - ORD

ANCORD

Anchorage

Fri 10/24

11:11 pm-8:40 am

Nonstop6h 29m

Chicago O'Hare Intl

Fri 10/31

2:54 pm-11:10 am

2 stops23h 16m

$338

AnchorageChicago

ANC - ORD

ANCORD

Anchorage

Mon 1/12

1:15 am-1:04 pm

1 stop8h 49m

Chicago O'Hare Intl

Sun 2/8

7:45 am-4:17 pm

1 stop11h 32m

$338

AnchorageChicago

ANC - ORD

ANCORD

Anchorage

Mon 1/12

1:45 am-1:04 pm

1 stop8h 19m

Chicago O'Hare Intl

Sun 2/8

7:45 am-4:17 pm

1 stop11h 32m

$338

AnchorageChicago

ANC - ORD

ANCORD

Anchorage

Thu 10/9

1:47 am-5:01 am

1 stop24h 14m

Chicago O'Hare Intl

Sat 10/18

8:20 am-12:18 pm

Nonstop6h 58m

$340

AnchorageChicago

ANC - ORD

ANCORD

Anchorage

Tue 11/18

10:00 am-12:24 am

1 stop11h 24m

Chicago O'Hare Intl

Fri 11/28

6:00 am-7:32 pm

1 stop16h 32m

$347

AnchorageChicago

ANC - ORD

ANCORD

Anchorage

Fri 11/14

11:05 am-5:01 am

2 stops14h 56m

Chicago O'Hare Intl

Sun 11/16

7:00 am-5:32 pm

1 stop13h 32m

$352

AnchorageChicago

ANC - MDW

ANCMDW

Anchorage

Wed 10/22

9:45 pm-8:55 am

1 stop8h 10m

Chicago Midway

Fri 10/24

7:10 pm-12:51 am

1 stop8h 41m

$356

AnchorageChicago

ANC - MDW

ANCMDW

Anchorage

Thu 10/9

6:05 am-5:43 pm

1 stop8h 38m

Chicago Midway

Mon 10/13

7:10 pm-12:51 am

1 stop8h 41m

$356

AnchorageChicago

ANC - MDW

ANCMDW

Anchorage

Mon 10/6

5:20 pm-8:40 am

2 stops12h 20m

Chicago Midway

Sat 10/11

1:06 pm-1:59 am

2 stops15h 53m

$366

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/14

Showing 1-10 of 42 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 September 15, 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 September 15, 2025.

The most flights from USAK to CHI are scheduled on a Thursday (9 on average). You will have fewer flight options on Monday, 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 Hawaiian Airlines, Alaska Airlines, or Delta 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 United Airlines, with whom users have recently found tickets for as low as $159. However, be on the lookout for offers from Alaska Airlines and Delta, 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: Air Canada (76%), United Airlines (76%), Qatar Airways (74%).

  • What are the cheapest flights from Alaska to Chicago?

    Looking for the cheapest flight from Alaska to Chicago? While on average our users pay $858, our data indicates the cheapest price to be $158. The most popular route (Anchorage - Chicago O'Hare Intl), is priced around $318.

  • 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 September 15, 2025.
AirlineCheapestAverageFlexibilityOn-time
Hawaiian AirlinesCheapest$187Average$461FlexibilityNo cancel feeOn-time85%
United AirlinesCheapest$328Average$494FlexibilityNo cancel feeOn-time69%
Alaska AirlinesCheapest$328Average$645FlexibilityNo cancel feeOn-time75%
DeltaCheapest$337Average$422FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$338Average$574FlexibilityNo cancel feeOn-time71%

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