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$159+ 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 11/11. Fares are subject to change and may not be available on all flights or dates of travel.
ANC — CHI
nov. 13 — nov. 201
jue. 11/13
jue. 11/20
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 octubre 14, 2025.

This KAYAK deal was found by Cheapflights users on 10/12. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 11/119:05 amANC - ORD
1 stop9h 35mAlaska Airlines
mar. 11/183:25 pmORD - ANC
1 stop10h 23mAlaska Airlines
Deal found 10/12$318
This Trip.com deal was found by Cheapflights users on 10/12. 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.
mié. 11/264:10 pmANC - ORD
1 stop19h 43mAlaska Airlines
mié. 12/310:00 amORD - ANC
1 stop29h 50mAlaska Airlines
Deal found 10/12$331
This Alaska Airlines deal was found by Cheapflights users on 10/14. 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.
sáb. 11/159:00 amANC - ORD
1 stop17h 01mAlaska Airlines
dom. 11/168:00 amORD - ANC
1 stop12h 22mAlaska Airlines
Deal found 10/14$332
This Delta deal was found by Cheapflights users on 10/14. 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.
dom. 11/96:00 amANC - ORD
1 stop8h 18mDelta
sáb. 11/226:45 amORD - ANC
1 stop15h 49mDelta
Deal found 10/14$338
This Delta deal was found by Cheapflights users on 10/14. 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.
mar. 11/119:45 pmANC - MDW
1 stop8h 16mDelta
mar. 11/187:02 pmMDW - ANC
1 stop8h 54mDelta
Deal found 10/14$338
This Delta deal was found by Cheapflights users on 10/13. 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.
mié. 12/35:55 amANC - ORD
1 stop15h 04mDelta
dom. 12/710:45 amORD - ANC
2 stops18h 08mDelta
Deal found 10/13$343
This Delta deal was found by Cheapflights users on 10/14. 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.
mar. 11/1112:30 amANC - MDW
2 stops14h 48mDelta
mié. 11/199:41 amMDW - ANC
1 stop12h 05mDelta
Deal found 10/14$343
This Delta deal was found by Cheapflights users on 10/14. 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.
lun. 12/155:55 amANC - MDW
2 stops24h 24mDelta
mié. 12/176:00 amMDW - ANC
2 stops22h 01mDelta
Deal found 10/14$353
This United Airlines deal was found by Cheapflights users on 10/12. 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.
mar. 11/259:07 pmANC - ORD
Nonstop6h 02mUnited Airlines
vie. 11/284:05 pmORD - ANC
Nonstop6h 54mUnited Airlines
Deal found 10/12$368
This Delta deal was found by Cheapflights users on 10/14. 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.
dom. 12/146:05 amANC - MDW
1 stop9h 13mDelta
jue. 12/186:00 amMDW - ANC
2 stops22h 01mDelta
Deal found 10/14$375
This Delta deal was found by Cheapflights users on 10/13. 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.
sáb. 12/135:37 pmANC - ORD
2 stops15h 03mDelta
mié. 12/179:45 amORD - ANC
2 stops18h 16mDelta
Deal found 10/13$380
This Delta deal was found by Cheapflights users on 10/14. 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.
lun. 12/155:55 amANC - MDW
2 stops24h 24mDelta
jue. 12/186:00 amMDW - ANC
2 stops22h 01mDelta
Deal found 10/14$383

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 octubre 14, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$313
(United Airlines)

One-way from

$159
(United Airlines)

Popular in

March

Cheapest in

October

Average price

$318

Good round-trip deal

$396 or less

Good one-way deal

$293 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. 17% potential increase in price ($108 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($16 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in October 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 octubre 14, 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

mar. 4/7

12:00 pm-5:00 am

1 stop14h 00m

Chicago O'Hare Intl

mié. 4/8

7:00 am-8:25 pm

1 stop16h 25m

$332

AnchorageChicago

ANC - ORD

ANCORD

Anchorage

mié. 11/12

6:00 am-5:18 pm

1 stop8h 18m

Chicago O'Hare Intl

sáb. 11/22

6:45 am-7:34 pm

1 stop15h 49m

$338

AnchorageChicago

ANC - ORD

ANCORD

Anchorage

lun. 11/10

4:30 pm-6:22 am

1 stop10h 52m

Chicago O'Hare Intl

dom. 11/16

7:00 am-1:32 pm

1 stop9h 32m

$338

AnchorageChicago

ANC - ORD

ANCORD

Anchorage

mar. 11/11

9:45 pm-8:30 am

1 stop7h 45m

Chicago O'Hare Intl

mar. 11/18

6:13 pm-1:57 am

1 stop10h 44m

$338

AnchorageChicago

ANC - ORD

ANCORD

Anchorage

lun. 11/10

10:00 am-9:40 pm

1 stop8h 40m

Chicago O'Hare Intl

jue. 11/20

3:25 pm-9:48 pm

1 stop9h 23m

$338

AnchorageChicago

ANC - ORD

ANCORD

Anchorage

mar. 11/4

12:30 am-1:30 pm

1 stop10h 00m

Chicago O'Hare Intl

vie. 12/12

6:10 pm-1:53 am

1 stop10h 43m

$338

AnchorageChicago

ANC - ORD

ANCORD

Anchorage

dom. 11/9

9:05 am-9:40 pm

1 stop9h 35m

Chicago O'Hare Intl

jue. 11/20

10:00 am-5:01 pm

1 stop10h 01m

$338

AnchorageChicago

ANC - ORD

ANCORD

Anchorage

mié. 12/3

5:55 am-11:59 pm

1 stop15h 04m

Chicago O'Hare Intl

dom. 12/7

6:10 pm-1:53 am

1 stop10h 43m

$338

AnchorageChicago

ANC - ORD

ANCORD

Anchorage

jue. 11/13

8:00 am-9:40 pm

1 stop10h 40m

Chicago O'Hare Intl

dom. 11/16

7:00 am-1:32 pm

1 stop9h 32m

$338

AnchorageChicago

ANC - ORD

ANCORD

Anchorage

lun. 2/9

1:20 am-1:25 pm

1 stop9h 05m

Chicago O'Hare Intl

vie. 2/13

9:30 am-7:10 pm

1 stop12h 40m

$338

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/12

Showing 1-10 of 41 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 $452). 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 octubre 14, 2025.

It’s optimal to fly from Alaska to Chicago in the afternoon. By choosing this option you can save up to 23% on the cost of your flight, compared to a flight in the morning.

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 octubre 14, 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 16m. Fly via Alaska Airlines or Delta to get the fastest option. Alaska and Chicago are separated by a distance of 2852 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 United Airlines, with whom users have recently found tickets for as low as $159. However, be on the lookout for offers from Alaska 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 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 (88%), Air Canada (84%), American Airlines (76%).

  • What are the cheapest flights from Alaska to Chicago?

    Looking for the cheapest flight from Alaska to Chicago? While on average our users pay $1,110, our data indicates the cheapest price to be $158. The most popular route (Anchorage - Chicago O'Hare Intl), is priced around $318.

  • 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 $452). 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
Merrillville
Lansing
Hammond
Porter
Benton Harbor
Chesterton

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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 octubre 14, 2025.
AirlineCheapestAverageFlexibilityOn-time
Hawaiian AirlinesCheapest$187Average$461FlexibilityNo cancel feeOn-time85%
United AirlinesCheapest$254Average$484FlexibilityNo cancel feeOn-time69%
DeltaCheapest$259Average$427FlexibilityNo cancel feeOn-timeN/A
Alaska AirlinesCheapest$318Average$641FlexibilityNo cancel feeOn-time75%
American AirlinesCheapest$338Average$513FlexibilityNo cancel feeOn-time71%

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