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$166+ 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 5/20. Fares are subject to change and may not be available on all flights or dates of travel.
ANC — CHI
Dec 26 — Jan 21
Fri 12/26
Fri 1/2
1 adult, Economy
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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 November 26, 2025.

This Delta deal was found by Cheapflights users on 11/25. 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 12/166:05 amANC - ORD
1 stop7h 52mDelta
Tue 1/612:30 pmORD - ANC
1 stop15h 18mDelta
Deal found 11/25$358
This Delta deal was found by Cheapflights users on 11/25. 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 12/166:05 amANC - MDW
1 stop9h 13mDelta
Tue 1/61:49 pmMDW - ANC
1 stop13h 59mDelta
Deal found 11/25$358
This Delta deal was found by Cheapflights users on 11/24. 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 12/251:15 amANC - ORD
1 stop9h 05mDelta
Sun 12/285:30 amORD - ANC
1 stop16h 27mDelta
Deal found 11/24$428
This Delta deal was found by Cheapflights users on 11/24. 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 - MDW
1 stop10h 51mDelta
Sun 12/286:00 amMDW - ANC
1 stop15h 57mDelta
Deal found 11/24$460
This Delta deal was found by Cheapflights users on 11/24. 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.
Wed 12/241:44 pmANC - ORD
2 stops16h 41mDelta
Sun 12/285:30 amORD - ANC
1 stop16h 27mDelta
Deal found 11/24$465
This Delta deal was found by Cheapflights users on 11/24. 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.
Mon 12/221:44 pmANC - ORD
2 stops19h 57mDelta
Wed 12/317:25 amORD - ANC
2 stops16h 15mDelta
Deal found 11/24$468
This Delta deal was found by Cheapflights users on 11/26. 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.
Mon 12/229:15 pmANC - ORD
1 stop11h 35mDelta
Fri 12/266:35 amORD - ANC
1 stop15h 14mDelta
Deal found 11/26$482
This Delta deal was found by Cheapflights users on 11/24. 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.
Wed 12/241:44 pmANC - MDW
2 stops16h 05mDelta
Sun 12/286:00 amMDW - ANC
1 stop15h 57mDelta
Deal found 11/24$497
This Delta deal was found by Cheapflights users on 11/24. 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 12/238:15 pmANC - MDW
1 stop15h 29mDelta
Sun 12/286:00 amMDW - ANC
1 stop15h 57mDelta
Deal found 11/24$510
This Delta deal was found by Cheapflights users on 11/24. 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.
Mon 12/812:30 amANC - ORD
1 stop10h 03mDelta
Mon 12/156:10 pmORD - ANC
1 stop10h 43mDelta
Deal found 11/24$524
This Alaska Airlines deal was found by Cheapflights users on 11/26. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/311:55 amFAI - ORD
1 stop12h 17mAlaska Airlines
Fri 1/98:00 amORD - FAI
1 stop14h 30mAlaska Airlines
Deal found 11/26$567
This Alaska Airlines deal was found by Cheapflights users on 11/26. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/3110:34 pmFAI - ORD
2 stops11h 42mAlaska Airlines
Thu 1/82:06 pmORD - FAI
2 stops13h 33mAlaska Airlines
Deal found 11/26$575

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 November 26, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$358
(Delta)

One-way from

$166
(Kiwi.com)

Popular in

March

Cheapest in

October

Average price

$398

Good round-trip deal

$666 or less

Good one-way deal

$318 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. 19% potential increase in price ($118 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($18 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in November 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 November 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

Mon 1/12

1:20 am-1:22 pm

1 stop9h 02m

Chicago O'Hare Intl

Sun 2/8

6:15 am-6:56 pm

1 stop15h 41m

$358

AnchorageChicago

ANC - ORD

ANCORD

Anchorage

Thu 5/7

6:00 am-11:58 pm

1 stop14h 58m

Chicago O'Hare Intl

Wed 5/13

6:00 am-1:10 pm

1 stop10h 10m

$358

AnchorageChicago

ANC - ORD

ANCORD

Anchorage

Mon 4/13

1:30 am-5:24 pm

1 stop12h 54m

Chicago O'Hare Intl

Sat 4/18

12:15 pm-6:48 pm

1 stop9h 33m

$358

AnchorageChicago

ANC - ORD

ANCORD

Anchorage

Tue 4/14

2:35 pm-5:00 am

1 stop11h 25m

Chicago O'Hare Intl

Sat 4/18

6:50 pm-1:28 am

1 stop9h 38m

$358

AnchorageChicago

ANC - ORD

ANCORD

Anchorage

Tue 2/10

9:15 pm-8:40 am

1 stop8h 25m

Chicago O'Hare Intl

Sat 2/14

7:40 am-2:21 pm

1 stop9h 41m

$358

AnchorageChicago

ANC - MDW

ANCMDW

Anchorage

Tue 12/16

6:05 am-6:18 pm

1 stop9h 13m

Chicago Midway

Tue 1/6

1:49 pm-12:48 am

1 stop13h 59m

$358

AnchorageChicago

ANC - MDW

ANCMDW

Anchorage

Tue 2/24

9:15 pm-9:06 am

1 stop8h 51m

Chicago Midway

Sat 2/28

11:45 am-6:57 pm

1 stop10h 12m

$358

AnchorageChicago

ANC - MDW

ANCMDW

Anchorage

Tue 2/10

9:15 pm-9:08 am

1 stop8h 53m

Chicago Midway

Sat 2/14

11:45 am-6:57 pm

1 stop10h 12m

$358

AnchorageChicago

ANC - MDW

ANCMDW

Anchorage

Fri 2/27

9:15 pm-11:03 am

1 stop10h 48m

Chicago Midway

Sun 3/1

9:50 am-6:57 pm

1 stop12h 07m

$358

SitkaChicago

SIT - ORD

SITORD

Sitka

Sat 2/14

11:26 am-11:56 pm

2 stops9h 30m

Chicago O'Hare Intl

Wed 2/18

7:00 am-6:29 pm

2 stops14h 29m

$502

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/25

Showing 1-10 of 47 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 July is currently the most expensive (average of $445). 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 November 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.

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 9h 02m. 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 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: Alaska Airlines (88%), United Airlines (87%), American Airlines (85%).

  • What are the cheapest flights from Alaska to Chicago?

    Looking for the cheapest flight from Alaska to Chicago? While on average our users pay $1,098, our data indicates the cheapest price to be $195. The most popular route (Anchorage - Chicago O'Hare Intl), is priced around $356.

  • 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 July is currently the most expensive (average of $445). 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
Hammond
Porter
Benton Harbor
Merrillville

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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 November 26, 2025.
AirlineCheapestAverageFlexibilityOn-time
Hawaiian AirlinesCheapest$187Average$461FlexibilityNo cancel feeOn-time85%
DeltaCheapest$259Average$432FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$314Average$504FlexibilityNo cancel feeOn-time69%
Alaska AirlinesCheapest$318Average$638FlexibilityNo cancel feeOn-time75%
American AirlinesCheapest$338Average$513FlexibilityNo cancel feeOn-time71%

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