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$154+ 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 5/13. Fares are subject to change and may not be available on all flights or dates of travel.
ANC — CHI
Mar 28 — Apr 41
Sat 3/28
Sat 4/4
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 February 26, 2026.

This United Airlines deal was found by Cheapflights users on 2/25. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/18:50 pm
ANC
-
ORD
Nonstop6h 15m
United Airlines
Wed 4/82:35 pm
ORD
-
ANC
1 stop11h 10m
United Airlines
Deal found 2/25$269
This Delta deal was found by Cheapflights users on 2/25. 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 3/311:34 am
ANC
-
ORD
1 stop8h 51m
Delta
Wed 4/87:25 am
ORD
-
ANC
1 stop10h 20m
Delta
Deal found 2/25$279
This Delta deal was found by Cheapflights users on 2/24. 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 4/151:30 am
ANC
-
ORD
1 stop8h 53m
Delta
Mon 4/2012:46 pm
ORD
-
ANC
1 stop11h 00m
Delta
Deal found 2/24$309
This Delta deal was found by Cheapflights users on 2/25. 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.
Mon 4/201:30 am
ANC
-
ORD
1 stop12h 09m
Delta
Sun 4/267:15 am
ORD
-
ANC
1 stop10h 18m
Delta
Deal found 2/25$324
This Delta deal was found by Cheapflights users on 2/26. 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.
Thu 5/79:59 pm
ANC
-
MDW
1 stop7h 43m
Delta
Wed 5/139:23 am
MDW
-
ANC
1 stop14h 26m
Delta
Deal found 2/26$324
This United Airlines deal was found by Cheapflights users on 2/25. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/319:04 pm
ANC
-
ORD
Nonstop6h 16m
United Airlines
Wed 4/14:03 pm
ORD
-
ANC
Nonstop6h 45m
United Airlines
Deal found 2/25$334
This Delta deal was found by Cheapflights users on 2/25. 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 3/241:34 am
ANC
-
ORD
1 stop8h 51m
Delta
Wed 4/12:20 pm
ORD
-
ANC
1 stop13h 09m
Delta
Deal found 2/25$339
This Delta deal was found by Cheapflights users on 2/24. 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 4/166:00 am
ANC
-
ORD
2 stops12h 18m
Delta
Thu 4/236:00 pm
ORD
-
ANC
1 stop9h 25m
Delta
Deal found 2/24$344
This United Airlines deal was found by Cheapflights users on 2/24. 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.
Thu 3/269:10 pm
ANC
-
ORD
Nonstop6h 07m
United Airlines
Mon 3/304:10 pm
ORD
-
ANC
Nonstop6h 45m
United Airlines
Deal found 2/24$349
This Delta deal was found by Cheapflights users on 2/26. 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.
Sat 4/188:25 pm
ANC
-
MDW
1 stop10h 31m
Delta
Thu 4/309:29 am
MDW
-
ANC
1 stop12h 17m
Delta
Deal found 2/26$396
This Delta deal was found by Cheapflights users on 2/25. 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.
Wed 4/19:15 pm
ANC
-
MDW
1 stop13h 10m
Delta
Wed 4/89:30 am
MDW
-
ANC
1 stop12h 21m
Delta
Deal found 2/25$401
This Delta deal was found by Cheapflights users on 2/22. 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 4/81:30 am
FAI
-
ORD
2 stops13h 32m
Delta
Thu 4/1612:46 pm
ORD
-
FAI
1 stop14h 54m
Delta
Deal found 2/22$404

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 February 26, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$309
(Delta)

One-way from

$154
(Delta)

Popular in

July

Cheapest in

October

Average price

$477

Good round-trip deal

$402 or less

Good one-way deal

$249 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. 4% potential increase in price ($19 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($12 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in February 2026
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 February 26, 2026.
Use the filters below to find and compare flights from Alaska to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

AnchorageChicago

ANC - ORD

ANCORD

Anchorage

Tue 3/31

9:04 pm-6:20 am

Nonstop6h 16m

Chicago O'Hare Intl

Wed 4/1

4:03 pm-7:48 pm

Nonstop6h 45m

$334

AnchorageChicago

ANC - MDW

ANCMDW

Anchorage

Thu 5/7

9:59 pm-12:42 pm

2 stops11h 43m

Chicago Midway

Wed 5/13

9:22 am-8:49 pm

2 stops14h 27m

$334

AnchorageChicago

ANC - ORD

ANCORD

Anchorage

Mon 4/27

1:41 pm-8:38 am

2 stops15h 57m

Chicago O'Hare Intl

Sat 5/2

7:15 am-2:33 pm

1 stop10h 18m

$344

AnchorageChicago

ANC - ORD

ANCORD

Anchorage

Thu 5/7

11:30 am-11:57 pm

1 stop9h 27m

Chicago O'Hare Intl

Wed 5/13

9:10 am-8:49 pm

2 stops14h 39m

$344

AnchorageChicago

ANC - ORD

ANCORD

Anchorage

Tue 3/31

6:00 am-11:59 pm

1 stop14h 59m

Chicago O'Hare Intl

Wed 4/1

8:20 am-9:35 pm

2 stops16h 15m

$374

AnchorageChicago

ANC - ORD

ANCORD

Anchorage

Tue 5/19

11:12 am-10:59 pm

1 stop8h 47m

Chicago O'Hare Intl

Sat 5/23

9:00 am-1:59 am

2 stops19h 59m

$374

AnchorageChicago

ANC - ORD

ANCORD

Anchorage

Wed 4/8

1:34 am-6:02 pm

2 stops13h 28m

Chicago O'Hare Intl

Thu 4/16

6:25 am-6:46 pm

1 stop15h 21m

$374

AnchorageChicago

ANC - ORD

ANCORD

Anchorage

Thu 5/28

9:59 pm-4:29 pm

2 stops15h 30m

Chicago O'Hare Intl

Tue 6/2

6:20 pm-12:55 am

1 stop9h 35m

$374

AnchorageChicago

ANC - ORD

ANCORD

Anchorage

Tue 4/14

1:41 pm-8:01 am

2 stops15h 20m

Chicago O'Hare Intl

Sun 4/19

6:25 am-6:46 pm

1 stop15h 21m

$374

AnchorageChicago

ANC - ORD

ANCORD

Anchorage

Fri 4/24

3:45 pm-10:19 am

2 stops15h 34m

Chicago O'Hare Intl

Mon 4/27

6:00 pm-12:25 am

1 stop9h 25m

$374

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/24

Showing 1-10 of 60 resultsSorted by cheapest first
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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 $697). 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.

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 16m. Fly via United Airlines, 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 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, Fairbanks - Chicago O'Hare Intl or Anchorage - Chicago Midway 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 (95%), United Airlines (95%), Korean Air (90%).

  • What are the cheapest flights from Alaska to Chicago?

    Looking for the cheapest flight from Alaska to Chicago? While on average our users pay $835, our data indicates the cheapest price to be $160. The most popular route (Anchorage - Chicago O'Hare Intl), is priced around $309.

  • 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 $697). 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 February 26, 2026.
AirlineCheapestAverageFlexibilityOn-time
Hawaiian AirlinesCheapest$158Average$461FlexibilityNo cancel feeOn-time85%
DeltaCheapest$187Average$395FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$262Average$476FlexibilityNo cancel feeOn-time69%
Alaska AirlinesCheapest$318Average$489FlexibilityNo cancel feeOn-time75%
American AirlinesCheapest$338Average$513FlexibilityNo cancel feeOn-time71%

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