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$169+ 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 6/21. Fares are subject to change and may not be available on all flights or dates of travel.
ANC — CHI
Jan 25 — Feb 11
Sun 1/25
Sun 2/1
1 adult, Economy
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Cheap 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 December 26, 2025.

This Delta deal was found by Cheapflights users on 12/24. 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 12/306:00 amANC - ORD
1 stop8h 47mDelta
Mon 1/52:20 pmORD - ANC
1 stop12h 49mDelta
Deal found 12/24$690
This Delta deal was found by Cheapflights users on 12/24. 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 12/308:15 pmANC - MDW
1 stop15h 29mDelta
Mon 1/59:50 amMDW - ANC
1 stop12h 06mDelta
Deal found 12/24$736
This Delta deal was found by Cheapflights users on 12/24. 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.
Sun 12/289:15 pmANC - ORD
1 stop11h 35mDelta
Mon 1/52:20 pmORD - ANC
1 stop12h 49mDelta
Deal found 12/24$751
This Delta deal was found by Cheapflights users on 12/26. 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.
Sun 12/289:15 pmANC - ORD
2 stops12h 39mDelta
Sat 1/36:00 amORD - ANC
1 stop9h 41mDelta
Deal found 12/26$756
This Delta deal was found by Cheapflights users on 12/24. 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.
Sun 12/289:15 pmANC - MDW
1 stop10h 51mDelta
Mon 1/55:31 pmMDW - ANC
2 stops34h 17mDelta
Deal found 12/24$763
This Delta deal was found by Cheapflights users on 12/23. 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 12/298:15 pmANC - ORD
1 stop12h 12mDelta
Fri 1/26:00 amORD - ANC
1 stop9h 41mDelta
Deal found 12/23$797
This Kiwi.com deal was found by Cheapflights users on 12/26. 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.
Sat 12/279:00 amANC - ORD
1 stop11h 59mAlaska Airlines
Sat 1/37:00 amORD - ANC
2 stops20h 44mAlaska Airlines
Deal found 12/26$801
This Delta deal was found by Cheapflights users on 12/24. 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.
Sun 12/286:00 amANC - MDW
1 stop8h 19mDelta
Sun 1/45:59 pmMDW - ANC
1 stop27h 57mDelta
Deal found 12/24$801
This United Airlines deal was found by Cheapflights users on 12/24. 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.
Sun 12/281:30 amANC - ORD
1 stop8h 49mUnited Airlines
Sun 1/43:42 pmORD - ANC
1 stop11h 43mUnited Airlines
Deal found 12/24$841
This Delta deal was found by Cheapflights users on 12/24. 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 12/269:15 pmANC - ORD
1 stop11h 35mDelta
Sun 1/47:25 amORD - ANC
2 stops16h 08mDelta
Deal found 12/24$862
This Delta deal was found by Cheapflights users on 12/24. 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 12/259:15 pmANC - MDW
1 stop10h 51mDelta
Mon 12/296:00 amMDW - ANC
1 stop15h 57mDelta
Deal found 12/24$897
This Delta deal was found by Cheapflights users on 12/24. 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 12/268:15 pmANC - MDW
1 stop16h 13mDelta
Sun 1/46:00 amMDW - ANC
1 stop15h 57mDelta
Deal found 12/24$1,057

Find flight deals from Alaska to Chicago

Keep the following information in mind while searching for Alaska to Chicago flight deals. Data was last updated December 26, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$357
(Kiwi.com)

One-way from

$169
(Alaska Airlines)

Popular in

March

Cheapest in

October

Average price

$408

Good round-trip deal

$747 or less

Good one-way deal

$282 or less
Provider with most accurate pricing for Anchorage-Chicago (CHI) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Anchorage-Chicago (CHI) flights.
Search Deals
From Alaska to Chicago (CHI)
Search Deals
One-way flight from Alaska to Chicago (CHI)
Search Deals
Highest demand for flights based on searches. 23% potential increase in price ($153 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 5% potential price decrease ($29 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
Search Deals
Price to beat on a round-trip flight from Alaska to Chicago (CHI).
Search Deals
Price to beat on a one-way flight from Alaska to Chicago (CHI).
Search Deals

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 December 26, 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

Wed 2/4

2:10 am-2:38 pm

1 stop9h 28m

Chicago O'Hare Intl

Fri 2/13

2:07 pm-12:30 am

1 stop13h 23m

$357

AnchorageChicago

ANC - ORD

ANCORD

Anchorage

Thu 2/5

5:05 am-5:10 pm

1 stop9h 05m

Chicago O'Hare Intl

Sat 2/14

5:29 pm-10:19 am

1 stop19h 50m

$357

AnchorageChicago

ANC - ORD

ANCORD

Anchorage

Wed 2/4

12:20 pm-11:50 pm

1 stop8h 30m

Chicago O'Hare Intl

Sun 2/15

5:29 pm-12:03 am

1 stop9h 34m

$357

AnchorageChicago

ANC - ORD

ANCORD

Anchorage

Tue 2/24

9:15 pm-8:40 am

1 stop8h 25m

Chicago O'Hare Intl

Sun 3/1

8:50 am-6:57 pm

1 stop13h 07m

$358

AnchorageChicago

ANC - MDW

ANCMDW

Anchorage

Thu 2/5

9:13 pm-9:08 am

1 stop8h 55m

Chicago Midway

Sun 2/15

11:45 am-6:57 pm

1 stop10h 12m

$358

AnchorageChicago

ANC - MDW

ANCMDW

Anchorage

Sat 2/7

9:15 pm-11:05 am

1 stop10h 50m

Chicago Midway

Wed 2/18

9:50 am-6:57 pm

1 stop12h 07m

$358

AnchorageChicago

ANC - ORD

ANCORD

Anchorage

Sun 2/8

12:49 am-1:10 pm

1 stop9h 21m

Chicago O'Hare Intl

Mon 2/23

5:29 pm-12:03 am

1 stop9h 34m

$358

AnchorageChicago

ANC - MDW

ANCMDW

Anchorage

Wed 2/4

9:15 pm-9:08 am

1 stop8h 53m

Chicago Midway

Tue 2/17

9:50 am-6:57 pm

1 stop12h 07m

$358

AnchorageChicago

ANC - ORD

ANCORD

Anchorage

Fri 4/24

7:00 am-7:52 pm

1 stop9h 52m

Chicago O'Hare Intl

Sun 4/26

6:00 am-2:02 pm

1 stop11h 02m

$358

AnchorageChicago

ANC - MDW

ANCMDW

Anchorage

Wed 2/4

9:15 pm-6:36 pm

1 stop18h 21m

Chicago Midway

Wed 2/18

9:50 am-6:57 pm

1 stop12h 07m

$358

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/24

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, May is the cheapest month in which you can book a flight from Alaska to Chicago (average of $187). Flying from Alaska to Chicago in January is currently the most expensive (average of $463). 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 December 26, 2025.

It’s optimal to fly from Alaska to Chicago in the afternoon. By choosing this option you can save up to 20% on the cost of your flight, compared to a flight in the evening.

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 December 26, 2025.

The most flights from USAK to CHI are scheduled on a Monday (2 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (2 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 8h 25m. Fly via 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 Hawaiian Airlines, with whom users have recently found tickets for as low as $156. However, be on the lookout for offers from United Airlines and Alaska 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 (84%), Alaska Airlines (80%), Korean Air (79%).

  • What are the cheapest flights from Alaska to Chicago?

    Looking for the cheapest flight from Alaska to Chicago? While on average our users pay $694, our data indicates the cheapest price to be $199. The most popular route (Anchorage - Chicago O'Hare Intl), is priced around $357.

  • 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, May is the cheapest month in which you can book a flight from Alaska to Chicago (average of $187). Flying from Alaska to Chicago in January is currently the most expensive (average of $463). 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
Lansing
Merrillville
Hammond
Porter
Benton Harbor

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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 December 26, 2025.
AirlineCheapestAverageFlexibilityOn-time
Hawaiian AirlinesCheapest$187Average$461FlexibilityNo cancel feeOn-time85%
DeltaCheapest$259Average$408FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$314Average$496FlexibilityNo cancel feeOn-time69%
Alaska AirlinesCheapest$318Average$637FlexibilityNo cancel feeOn-time75%
American AirlinesCheapest$338Average$513FlexibilityNo cancel feeOn-time71%

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