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$185+ 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 10/1. Fares are subject to change and may not be available on all flights or dates of travel.
ANC — CHI
Jun 27 — Jul 41
Sat 6/27
Sat 7/4
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 May 28, 2026.

This American Airlines deal was found by Cheapflights users on 5/27. 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.
Thu 9/39:56 pm
ANC
-
ORD
Nonstop6h 29m
American Airlines
Mon 9/74:57 pm
ORD
-
ANC
Nonstop6h 54m
American Airlines
Deal found 5/27$373
This SmartFares deal was found by Cheapflights users on 5/23. 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 SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/79:24 pm
ANC
-
ORD
Nonstop6h 16m
Alaska Airlines
Mon 7/1312:59 am
ORD
-
ANC
Nonstop6h 42m
Alaska Airlines
Deal found 5/23$382
This Alaska Airlines deal was found by Cheapflights users on 5/24. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/2010:28 pm
ANC
-
ORD
Nonstop6h 12m
Alaska Airlines
Mon 8/246:00 am
ORD
-
ANC
1 stop19h 45m
Alaska Airlines
Deal found 5/24$383
This Alaska Airlines deal was found by Cheapflights users on 5/25. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/410:28 pm
ANC
-
ORD
Nonstop6h 12m
Alaska Airlines
Mon 9/77:20 am
ORD
-
ANC
Nonstop6h 52m
Alaska Airlines
Deal found 5/25$386
This Delta deal was found by Cheapflights users on 5/27. 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 9/310:37 pm
ANC
-
ORD
1 stop11h 36m
Delta
Mon 9/76:44 pm
ORD
-
ANC
1 stop9h 15m
Delta
Deal found 5/27$393
This Delta deal was found by Cheapflights users on 5/23. 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.
Thu 9/310:37 pm
ANC
-
MDW
1 stop11h 02m
Delta
Tue 9/89:30 am
MDW
-
ANC
1 stop14h 28m
Delta
Deal found 5/23$393
This American Airlines deal was found by Cheapflights users on 5/28. 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.
Fri 9/411:41 pm
ANC
-
ORD
1 stop11h 41m
American Airlines
Mon 9/74:57 pm
ORD
-
ANC
Nonstop6h 54m
American Airlines
Deal found 5/28$396
This Delta deal was found by Cheapflights users on 5/23. 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.
Thu 9/38:20 pm
ANC
-
MDW
2 stops13h 19m
Delta
Mon 9/79:24 am
MDW
-
ANC
1 stop14h 32m
Delta
Deal found 5/23$398
This United Airlines deal was found by Cheapflights users on 5/26. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/128:55 pm
ANC
-
ORD
Nonstop6h 18m
United Airlines
Mon 11/164:05 pm
ORD
-
ANC
Nonstop6h 40m
United Airlines
Deal found 5/26$399
This Delta deal was found by Cheapflights users on 5/27. 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 9/101:30 am
ANC
-
ORD
2 stops12h 18m
Delta
Sun 9/131:35 pm
ORD
-
ANC
2 stops13h 58m
Delta
Deal found 5/27$403
This Delta deal was found by Cheapflights users on 5/26. 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 11/122:20 pm
ANC
-
MDW
2 stops15h 29m
Delta
Mon 11/1612:30 pm
MDW
-
ANC
2 stops13h 06m
Delta
Deal found 5/26$403
This Alaska Airlines deal was found by Cheapflights users on 5/24. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/226:00 am
ANC
-
ORD
1 stop9h 20m
Alaska Airlines
Sat 10/249:00 am
ORD
-
ANC
1 stop9h 52m
Alaska Airlines
Deal found 5/24$406

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 May 28, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$373
(American Airlines)

One-way from

$185
(American Airlines)

Popular in

July

Cheapest in

October

Average price

$469

Good round-trip deal

$544 or less

Good one-way deal

$308 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. 9% potential increase in price ($42 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($8 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in May 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 May 28, 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

Cheapest round-trip
Quickest round-trip

AnchorageChicago

ANC - ORD

ANCORD

Anchorage

Thu 8/20

10:28 pm-7:40 am

Nonstop6h 12m

Chicago O'Hare Intl

Mon 8/24

7:20 am-11:12 am

Nonstop6h 52m

$373

AnchorageChicago

ANC - ORD

ANCORD

Anchorage

Thu 9/3

6:00 am-11:28 pm

1 stop14h 28m

Chicago O'Hare Intl

Mon 9/7

7:00 am-4:26 pm

1 stop12h 26m

$393

AnchorageChicago

ANC - MDW

ANCMDW

Anchorage

Thu 8/20

10:37 pm-12:39 pm

1 stop11h 02m

Chicago Midway

Mon 8/24

1:51 pm-9:24 pm

1 stop10h 33m

$393

AnchorageChicago

ANC - ORD

ANCORD

Anchorage

Fri 8/14

6:00 am-11:28 pm

1 stop14h 28m

Chicago O'Hare Intl

Mon 8/17

1:41 pm-11:24 pm

2 stops12h 43m

$398

AnchorageChicago

ANC - ORD

ANCORD

Anchorage

Fri 8/21

1:32 am-1:23 pm

1 stop8h 51m

Chicago O'Hare Intl

Sat 9/5

8:28 am-8:08 pm

2 stops14h 40m

$398

AnchorageChicago

ANC - ORD

ANCORD

Anchorage

Fri 9/4

11:01 am-11:38 pm

1 stop9h 37m

Chicago O'Hare Intl

Mon 9/7

7:45 am-4:26 pm

2 stops11h 41m

$398

AnchorageChicago

ANC - ORD

ANCORD

Anchorage

Thu 9/10

1:30 am-1:30 pm

1 stop9h 00m

Chicago O'Hare Intl

Sun 9/13

7:10 am-7:27 pm

2 stops15h 17m

$398

AnchorageChicago

ANC - MDW

ANCMDW

Anchorage

Thu 11/12

2:20 pm-8:49 am

2 stops15h 29m

Chicago Midway

Mon 11/16

12:30 pm-10:36 pm

2 stops13h 06m

$403

AnchorageChicago

ANC - ORD

ANCORD

Anchorage

Thu 6/25

1:30 am-6:58 pm

2 stops14h 28m

Chicago O'Hare Intl

Fri 7/3

5:55 pm-11:56 pm

1 stop9h 01m

$411

AnchorageChicago

ANC - MDW

ANCMDW

Anchorage

Fri 6/26

2:10 pm-8:37 am

2 stops15h 27m

Chicago Midway

Fri 7/3

9:17 am-11:20 pm

2 stops17h 03m

$444

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/26

Showing 1-10 of 58 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, August is the cheapest month in which you can book a flight from Alaska to Chicago (average of $158). Flying from Alaska to Chicago in January is currently the most expensive (average of $408). 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 May 28, 2026.

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 May 28, 2026.

The most flights from USAK to CHI are scheduled on a Monday (11 on average). You will have fewer flight options on Saturday, 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?

How far ahead should I book a flight from Alaska to Chicago?

To ensure you get the cheapest price possible for a flight from Alaska to Chicago, you should look to book at least 73 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.

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 12m. Fly via Alaska Airlines, Delta, or Southwest 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 Alaska Airlines and United 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: Qatar Airways (100%), Alaska Airlines (100%), Air Canada (88%).

  • What are the cheapest flights from Alaska to Chicago?

    Looking for the cheapest flight from Alaska to Chicago? While on average our users pay $592, our data indicates the cheapest price to be $206. The most popular route (Anchorage - Chicago O'Hare Intl), is priced around $393.

  • 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 $158). Flying from Alaska to Chicago in January is currently the most expensive (average of $408). 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
Benton Harbor
Lansing
Merrillville
Hammond
Porter

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Alternative routes for Alaska to Chicago

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Top 4 airlines flying from Alaska to Chicago

Discover the top 4 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 May 28, 2026.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$314Average$530FlexibilityNo cancel feeOn-time69%
Alaska AirlinesCheapest$318Average$482FlexibilityNo cancel feeOn-time75%
American AirlinesCheapest$331Average$418FlexibilityNo cancel feeOn-time71%
DeltaCheapest$337Average$480FlexibilityNo cancel feeOn-timeN/A

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