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$187+ 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 5/16. Fares are subject to change and may not be available on all flights or dates of travel.
ANC — CHI
Apr 6 — Apr 131
Sun 4/6
Sun 4/13
1 adult, Economy
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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 April 1, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$396
(Delta)

One-way from

$187
(American Airlines)

Popular in

March

Cheapest in

November

Average price

$542

Good round-trip deal

$549 or less

Good one-way deal

$263 or less
Provider with most accurate pricing for Anchorage-Chicago (CHI) flight deals.
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Provider most trusted by Cheapflights users for Anchorage-Chicago (CHI) flights.
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From Alaska to Chicago (CHI)
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One-way flight from Alaska to Chicago (CHI)
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Highest demand for flights based on searches. 13% potential increase in price ($80 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($13 potential savings vs. average RT price).
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Average for round-trip flights in April 2025
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Price to beat on a round-trip flight from Alaska to Chicago (CHI).
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Price to beat on a one-way flight from Alaska to Chicago (CHI).
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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 April 1, 2025.

This Delta deal was found by Cheapflights users on 3/31. 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 5/2912:55 amANC - ORD
1 stop9h 35mDelta
Sun 6/17:15 amORD - ANC
1 stop9h 10mDelta
Deal found 3/31$396
This Delta deal was found by Cheapflights users on 4/1. 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 4/281:26 amANC - MDW
2 stops12h 53mDelta
Tue 5/61:16 pmMDW - ANC
1 stop8h 50mDelta
Deal found 4/1$421
This American Airlines deal was found by Cheapflights users on 4/1. 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 5/299:48 pmANC - ORD
Nonstop6h 16mAmerican Airlines
Sat 6/72:40 pmORD - ANC
1 stop11h 03mAmerican Airlines
Deal found 4/1$437
This Alaska Airlines deal was found by Cheapflights users on 3/31. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/1710:36 pmANC - ORD
Nonstop6h 34mAlaska Airlines
Tue 5/207:59 pmORD - ANC
1 stop30h 45mAlaska Airlines
Deal found 3/31$443
This United Airlines deal was found by Cheapflights users on 4/1. 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 4/298:30 pmANC - ORD
Nonstop6h 20mUnited Airlines
Tue 5/61:05 pmORD - ANC
Nonstop6h 39mUnited Airlines
Deal found 4/1$449
This Hawaiian Airlines deal was found by Cheapflights users on 4/1. 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 Hawaiian Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/211:26 pmANC - ORD
Nonstop6h 14mHawaiian Airlines
Mon 7/712:59 amORD - ANC
Nonstop6h 38mHawaiian Airlines
Deal found 4/1$452
This Alaska Airlines deal was found by Cheapflights users on 3/30. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/58:57 pmFAI - ORD
2 stops13h 12mAlaska Airlines
Sat 9/208:59 pmORD - FAI
2 stops20h 34mAlaska Airlines
Deal found 3/30$575
This American Airlines deal was found by Cheapflights users on 3/31. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/145:00 pmFAI - ORD
1 stop11h 04mAmerican Airlines
Wed 5/212:50 pmORD - FAI
1 stop14h 30mAmerican Airlines
Deal found 3/31$586
This Delta deal was found by Cheapflights users on 3/30. 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.
Fri 9/510:05 pmFAI - ORD
1 stop7h 26mDelta
Sat 9/207:30 amORD - FAI
1 stop9h 51mDelta
Deal found 3/30$607
This United Airlines deal was found by Cheapflights users on 3/30. 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.
Fri 9/511:20 pmFAI - ORD
1 stop9h 22mUnited Airlines
Sat 9/204:15 pmORD - FAI
Nonstop6h 33mUnited Airlines
Deal found 3/30$642
This Delta deal was found by Cheapflights users on 3/31. 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.
Tue 5/131:45 amFAI - MDW
2 stops14h 00mDelta
Wed 5/211:08 pmMDW - FAI
2 stops14h 20mDelta
Deal found 3/31$983

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 April 1, 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

Thu 5/29

6:05 am-5:25 pm

1 stop8h 20m

Chicago O'Hare Intl

Thu 6/5

2:25 pm-11:25 pm

1 stop12h 00m

$396

AnchorageChicago

ANC - MDW

ANCMDW

Anchorage

Mon 4/28

1:26 am-5:19 pm

2 stops12h 53m

Chicago Midway

Tue 5/6

1:16 pm-7:06 pm

1 stop8h 50m

$421

AnchorageChicago

ANC - ORD

ANCORD

Anchorage

Thu 5/29

9:48 pm-7:04 am

Nonstop6h 16m

Chicago O'Hare Intl

Sat 6/7

2:40 pm-10:43 pm

1 stop11h 03m

$437

AnchorageChicago

ANC - ORD

ANCORD

Anchorage

Sat 5/17

10:36 pm-8:10 am

Nonstop6h 34m

Chicago O'Hare Intl

Tue 5/20

7:59 pm-11:44 pm

1 stop30h 45m

$443

AnchorageChicago

ANC - ORD

ANCORD

Anchorage

Tue 4/29

8:30 pm-5:50 am

Nonstop6h 20m

Chicago O'Hare Intl

Tue 5/6

1:05 pm-4:44 pm

Nonstop6h 39m

$449

AnchorageChicago

ANC - ORD

ANCORD

Anchorage

Thu 6/26

9:08 pm-6:24 am

Nonstop6h 16m

Chicago O'Hare Intl

Sun 6/29

12:59 am-4:37 am

Nonstop6h 38m

$541

FairbanksChicago

FAI - ORD

FAIORD

Fairbanks

Fri 9/5

8:57 pm-1:09 pm

2 stops13h 12m

Chicago O'Hare Intl

Sat 9/20

8:59 pm-2:33 pm

2 stops20h 34m

$575

FairbanksChicago

FAI - ORD

FAIORD

Fairbanks

Wed 5/14

5:00 pm-7:04 am

1 stop11h 04m

Chicago O'Hare Intl

Wed 5/21

2:50 pm-2:20 am

1 stop14h 30m

$586

FairbanksChicago

FAI - ORD

FAIORD

Fairbanks

Fri 9/5

10:05 pm-8:31 am

1 stop7h 26m

Chicago O'Hare Intl

Sat 9/20

7:30 am-2:21 pm

1 stop9h 51m

$607

FairbanksChicago

FAI - ORD

FAIORD

Fairbanks

Fri 9/5

11:20 pm-11:42 am

1 stop9h 22m

Chicago O'Hare Intl

Sat 9/20

4:15 pm-7:48 pm

Nonstop6h 33m

$642

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/31

Showing 1-10 of 24 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, August is the cheapest month in which you can book a flight from Alaska to Chicago (average of $245). Flying from Alaska to Chicago in March is currently the most expensive (average of $323). 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 April 1, 2025.

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 April 1, 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).

Rainfall in Chicago by month

Plan your trip to Chicago by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Chicago ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago when rainfall is around 1.7 in.

Temperature in Chicago by month

Plan your trip to Chicago by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Chicago, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

Reviews of airlines servicing Chicago

Get insights into the airlines that provide service to Chicago. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Chicago. Reviews last updated April 1, 2025.
See what other customers who have flown with Alaska Airlines, Delta and Hawaiian Airlines from Alaska to Chicago have to say. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Alaska Airlines
8.0
Very good
9,820 reviews

Overall

8.0

Comfort

7.9

Food

7.1

Entertainment

7.1

Crew

8.5

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them
Alaska Airlines
8.0
Very good
9,820 reviews
Alaska Airlines
8.0
Very good
9,820 reviews

Overall

8.0

Comfort

7.9

Food

7.1

Entertainment

7.1

Crew

8.5

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them
Delta
8.0
Very good
7,898 reviews
Alaska Airlines
8.0
Very good
9,820 reviews

Overall

8.0

Comfort

7.9

Food

7.1

Entertainment

7.1

Crew

8.5

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them
Hawaiian Airlines
7.9
Good
2,345 reviews
Alaska Airlines
8.0
Very good
9,820 reviews

Overall

8.0

Comfort

7.9

Food

7.1

Entertainment

7.1

Crew

8.5

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them
United Airlines
7.4
Good
8,615 reviews
Alaska Airlines
8.0
Very good
9,820 reviews

Overall

8.0

Comfort

7.9

Food

7.1

Entertainment

7.1

Crew

8.5

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them
American Airlines
7.2
Good
10,000 reviews
Alaska Airlines
8.0
Very good
9,820 reviews

Overall

8.0

Comfort

7.9

Food

7.1

Entertainment

7.1

Crew

8.5

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them

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.

  • What are the cheapest airlines to fly from Alaska to Chicago one-way?

    The cheapest airline one-way is American Airlines, with whom users have recently found tickets for as low as $187. However, be on the lookout for offers from Alaska Airlines and Hawaiian 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: Korean Air (65%), Atlas Air (55%), Cathay Pacific (49%).

  • What are the cheapest flights from Alaska to Chicago?

    Looking for the cheapest flight from Alaska to Chicago? While on average our users pay $1,164, our data indicates the cheapest price to be $199. The most popular route (Anchorage - Chicago O'Hare Intl), is priced around $386.

  • 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 $245). Flying from Alaska to Chicago in March is currently the most expensive (average of $323). 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 Alaska?

Book flights to Alaska if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Benton Harbor
Porter
Lansing
Valparaiso
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 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 April 1, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$259Average$416FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$338Average$467FlexibilityNo cancel feeOn-time71%
Alaska AirlinesCheapest$339Average$657FlexibilityNo cancel feeOn-time75%
United AirlinesCheapest$345Average$486FlexibilityNo cancel feeOn-time69%

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