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$206+ 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 9/3. Fares are subject to change and may not be available on all flights or dates of travel.
ANC — CHI
Sep 2 — Sep 91
Wed 9/2
Wed 9/9
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 August 3, 2026.

This SmartFares deal was found by Cheapflights users on 7/30. 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.
Thu 8/2710:28 pm
ANC
-
ORD
Nonstop6h 12m
Alaska Airlines
Thu 9/37:20 am
ORD
-
ANC
Nonstop6h 52m
Alaska Airlines
Deal found 7/30$405
This United Airlines deal was found by Cheapflights users on 7/30. 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 9/38:00 pm
ANC
-
ORD
Nonstop6h 12m
United Airlines
Tue 9/84:05 pm
ORD
-
ANC
Nonstop6h 54m
United Airlines
Deal found 7/30$413
This American Airlines deal was found by Cheapflights users on 7/30. 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.
Wed 8/269:56 pm
ANC
-
ORD
Nonstop6h 29m
American Airlines
Mon 8/314:57 pm
ORD
-
ANC
Nonstop6h 54m
American Airlines
Deal found 7/30$417
This Trip.com deal was found by Cheapflights users on 7/31. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/3010:28 pm
ANC
-
ORD
Nonstop6h 12m
Alaska Airlines
Sat 9/57:20 am
ORD
-
ANC
Nonstop6h 52m
Alaska Airlines
Deal found 7/31$418
This Trip.com deal was found by Cheapflights users on 8/2. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/310:28 pm
ANC
-
ORD
Nonstop6h 12m
Alaska Airlines
Wed 9/96:00 am
ORD
-
ANC
1 stop9h 59m
Alaska Airlines
Deal found 8/2$420
This American Airlines deal was found by Cheapflights users on 7/29. 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.
Wed 8/269:56 pm
ANC
-
ORD
Nonstop6h 29m
American Airlines
Sun 8/304:57 pm
ORD
-
ANC
Nonstop6h 54m
American Airlines
Deal found 7/29$421
This United Airlines deal was found by Cheapflights users on 7/30. 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 9/38:19 pm
ANC
-
ORD
1 stop11h 39m
United Airlines
Mon 9/79:06 am
ORD
-
ANC
Nonstop6h 58m
United Airlines
Deal found 7/30$423
This United Airlines deal was found by Cheapflights users on 7/29. 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 8/2611:09 pm
ANC
-
ORD
1 stop9h 19m
United Airlines
Wed 9/24:05 pm
ORD
-
ANC
Nonstop6h 54m
United Airlines
Deal found 7/29$427
This United Airlines deal was found by Cheapflights users on 7/30. 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.
Mon 8/318:15 pm
ANC
-
ORD
1 stop12h 31m
United Airlines
Wed 9/24:05 pm
ORD
-
ANC
Nonstop6h 54m
United Airlines
Deal found 7/30$431
This Delta deal was found by Cheapflights users on 7/30. 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 8/3110:10 pm
ANC
-
MDW
1 stop12h 00m
Delta
Wed 9/21:51 pm
MDW
-
ANC
1 stop10h 09m
Delta
Deal found 7/30$441
This Delta deal was found by Cheapflights users on 7/31. 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 9/310:10 pm
ANC
-
MDW
1 stop7h 29m
Delta
Tue 9/89:59 am
MDW
-
ANC
1 stop14h 01m
Delta
Deal found 7/31$443
This United Airlines deal was found by Cheapflights users on 7/30. 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 8/268:27 pm
FAI
-
ORD
Nonstop5h 58m
United Airlines
Sun 8/303:35 pm
ORD
-
FAI
Nonstop6h 41m
United Airlines
Deal found 7/30$443

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 August 3, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$405
(SmartFares)

One-way from

$206
(American Airlines)

Popular in

July

Cheapest in

October

Average price

$393

Good round-trip deal

$281 or less

Good one-way deal

$294 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 ($47 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($11 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in August 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 August 3, 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 9/3

10:28 pm-7:40 am

Nonstop6h 12m

Chicago O'Hare Intl

Mon 9/7

7:20 am-11:12 am

Nonstop6h 52m

$423

AnchorageChicago

ANC - ORD

ANCORD

Anchorage

Thu 9/3

9:20 pm-6:32 am

Nonstop6h 12m

Chicago O'Hare Intl

Mon 9/7

4:05 pm-7:59 pm

Nonstop6h 54m

$423

AnchorageChicago

ANC - ORD

ANCORD

Anchorage

Mon 8/31

8:15 pm-11:46 am

1 stop12h 31m

Chicago O'Hare Intl

Wed 9/2

4:05 pm-7:59 pm

Nonstop6h 54m

$431

AnchorageChicago

ANC - ORD

ANCORD

Anchorage

Sun 8/30

1:32 am-1:23 pm

1 stop8h 51m

Chicago O'Hare Intl

Tue 9/8

12:29 pm-9:00 pm

1 stop11h 31m

$433

AnchorageChicago

ANC - ORD

ANCORD

Anchorage

Tue 9/29

6:07 am-11:59 pm

1 stop14h 52m

Chicago O'Hare Intl

Wed 10/14

7:00 am-8:51 pm

1 stop16h 51m

$433

AnchorageChicago

ANC - ORD

ANCORD

Anchorage

Thu 9/3

11:01 am-11:29 pm

1 stop9h 28m

Chicago O'Hare Intl

Mon 9/7

6:00 am-11:39 am

1 stop8h 39m

$433

AnchorageChicago

ANC - ORD

ANCORD

Anchorage

Tue 9/1

8:15 pm-9:38 am

1 stop10h 23m

Chicago O'Hare Intl

Mon 9/7

9:06 am-1:04 pm

Nonstop6h 58m

$433

AnchorageChicago

ANC - ORD

ANCORD

Anchorage

Thu 9/3

8:15 pm-9:38 am

1 stop10h 23m

Chicago O'Hare Intl

Tue 9/8

5:51 pm-11:59 pm

1 stop9h 08m

$433

AnchorageChicago

ANC - ORD

ANCORD

Anchorage

Tue 10/20

8:59 pm-6:10 am

Nonstop6h 11m

Chicago O'Hare Intl

Tue 11/3

4:20 pm-10:56 pm

1 stop9h 36m

$433

AnchorageChicago

ANC - ORD

ANCORD

Anchorage

Wed 8/26

10:28 pm-7:40 am

Nonstop6h 12m

Chicago O'Hare Intl

Mon 8/31

7:20 am-11:12 am

Nonstop6h 52m

$441

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/2

Showing 1-10 of 59 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, February is the cheapest month in which you can book a flight from Alaska to Chicago (average of $358). Flying from Alaska to Chicago in January is currently the most expensive (average of $734). 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 August 3, 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 August 3, 2026.

The most flights from USAK to CHI are scheduled on a Monday (10 on average). You will have fewer flight options on Wednesday, which is when the least amount of flights are scheduled (8 on average).

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, United 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 Alaska Airlines, with whom users have recently found tickets for as low as $158. However, be on the lookout for offers from United 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 Nome - 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 (83%), United Airlines (82%), Alaska Airlines (71%).

  • What are the cheapest flights from Alaska to Chicago?

    Looking for the cheapest flight from Alaska to Chicago? While on average our users pay $879, our data indicates the cheapest price to be $196. The most popular route (Anchorage - Chicago O'Hare Intl), is priced around $417.

  • 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, February is the cheapest month in which you can book a flight from Alaska to Chicago (average of $358). Flying from Alaska to Chicago in January is currently the most expensive (average of $734). 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
Valparaiso
Hammond
Saint Joseph
Porter

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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 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 August 3, 2026.
AirlineCheapestAverageFlexibilityOn-time
Alaska AirlinesCheapest$204Average$526FlexibilityNo cancel feeOn-time75%
United AirlinesCheapest$314Average$544FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$318Average$419FlexibilityNo cancel feeOn-time71%
DeltaCheapest$337Average$480FlexibilityNo cancel feeOn-timeN/A

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