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$173+ 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 9/16. Fares are subject to change and may not be available on all flights or dates of travel.
ANC — CHI
Jul 8 — Jul 151
Tue 7/8
Tue 7/15
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 July 3, 2025.

Round-trip from

$346
(American Airlines)

One-way from

$173
(American Airlines)

Popular in

March

Cheapest in

November

Average price

$574

Good round-trip deal

$563 or less

Good one-way deal

$313 or less
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. 14% potential increase in price ($87 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($12 potential savings vs. average RT price).
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Average for round-trip flights in July 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 July 3, 2025.

This American Airlines deal was found by Cheapflights users on 6/30. 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.
Tue 9/169:53 pmANC - ORD
Nonstop6h 24mAmerican Airlines
Sat 9/205:01 pmORD - ANC
Nonstop6h 47mAmerican Airlines
Deal found 6/30$346
This Kiwi.com deal was found by Cheapflights users on 7/3. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/2411:25 pmANC - ORD
Nonstop6h 15mHawaiian Airlines
Mon 9/18:40 amORD - ANC
Nonstop6h 41mHawaiian Airlines
Deal found 7/3$347
This Alaska Airlines deal was found by Cheapflights users on 6/30. 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.
Mon 9/152:45 amANC - ORD
1 stop8h 39mAlaska Airlines
Sat 9/208:40 amORD - ANC
Nonstop6h 41mAlaska Airlines
Deal found 6/30$356
This Delta deal was found by Cheapflights users on 7/3. 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 10/112:55 amANC - ORD
1 stop9h 35mDelta
Sat 10/112:25 pmORD - ANC
1 stop14h 20mDelta
Deal found 7/3$372
This Delta deal was found by Cheapflights users on 7/1. 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.
Fri 9/510:30 pmANC - MDW
1 stop10h 58mDelta
Tue 9/97:17 pmMDW - ANC
1 stop9h 18mDelta
Deal found 7/1$372
This United Airlines deal was found by Cheapflights users on 7/2. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/29:04 pmANC - ORD
Nonstop6h 09mUnited Airlines
Mon 10/64:10 pmORD - ANC
Nonstop6h 47mUnited Airlines
Deal found 7/2$432
This Delta deal was found by Cheapflights users on 7/3. 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 8/1610:07 pmFAI - MDW
1 stop7h 43mDelta
Sat 8/239:15 amMDW - FAI
1 stop14h 42mDelta
Deal found 7/3$487
This Delta deal was found by Cheapflights users on 7/3. 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 8/1512:30 amFAI - ORD
1 stop8h 28mDelta
Sat 8/2310:30 amORD - FAI
1 stop13h 27mDelta
Deal found 7/3$487
This Alaska Airlines deal was found by Cheapflights users on 7/3. 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 8/152:09 amFAI - ORD
2 stops18h 30mAlaska Airlines
Sat 8/232:07 pmORD - FAI
2 stops13h 41mAlaska Airlines
Deal found 7/3$551
This Hawaiian Airlines deal was found by Cheapflights users on 7/2. 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 Hawaiian Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/179:25 pmFAI - ORD
1 stop8h 15mHawaiian Airlines
Sun 7/2012:59 amORD - FAI
1 stop11h 06mHawaiian Airlines
Deal found 7/2$634
This United Airlines deal was found by Cheapflights users on 7/3. 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.
Sat 8/1611:23 pmFAI - ORD
1 stop10h 57mUnited Airlines
Sat 8/234:15 pmORD - FAI
Nonstop6h 33mUnited Airlines
Deal found 7/3$772
This Alaska Airlines deal was found by Cheapflights users on 7/2. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/171:40 pmSIT - ORD
1 stop13h 00mAlaska Airlines
Mon 7/218:00 amORD - SIT
1 stop17h 44mAlaska Airlines
Deal found 7/2$905

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 July 3, 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

Tue 9/16

9:53 pm-7:17 am

Nonstop6h 24m

Chicago O'Hare Intl

Sat 9/20

5:01 pm-8:48 pm

Nonstop6h 47m

$346

AnchorageChicago

ANC - ORD

ANCORD

Anchorage

Sun 8/24

11:25 pm-8:40 am

Nonstop6h 15m

Chicago O'Hare Intl

Mon 9/1

8:40 am-12:21 pm

Nonstop6h 41m

$347

AnchorageChicago

ANC - ORD

ANCORD

Anchorage

Mon 9/15

2:45 am-2:24 pm

1 stop8h 39m

Chicago O'Hare Intl

Sat 9/20

8:40 am-12:21 pm

Nonstop6h 41m

$356

AnchorageChicago

ANC - ORD

ANCORD

Anchorage

Wed 10/1

12:55 am-1:30 pm

1 stop9h 35m

Chicago O'Hare Intl

Sat 10/11

2:25 pm-1:45 am

1 stop14h 20m

$372

AnchorageChicago

ANC - MDW

ANCMDW

Anchorage

Fri 9/5

10:30 pm-12:28 pm

1 stop10h 58m

Chicago Midway

Tue 9/9

7:17 pm-1:35 am

1 stop9h 18m

$372

AnchorageChicago

ANC - ORD

ANCORD

Anchorage

Thu 10/2

9:04 pm-6:13 am

Nonstop6h 09m

Chicago O'Hare Intl

Mon 10/6

4:10 pm-7:57 pm

Nonstop6h 47m

$432

FairbanksChicago

FAI - MDW

FAIMDW

Fairbanks

Sat 8/16

10:07 pm-8:50 am

1 stop7h 43m

Chicago Midway

Sat 8/23

9:15 am-8:57 pm

1 stop14h 42m

$487

FairbanksChicago

FAI - ORD

FAIORD

Fairbanks

Fri 8/15

12:30 am-11:58 am

1 stop8h 28m

Chicago O'Hare Intl

Sat 8/23

10:30 am-8:57 pm

1 stop13h 27m

$487

FairbanksChicago

FAI - ORD

FAIORD

Fairbanks

Fri 8/15

2:09 am-11:39 pm

2 stops18h 30m

Chicago O'Hare Intl

Sat 8/23

2:07 pm-12:48 am

2 stops13h 41m

$551

FairbanksChicago

FAI - ORD

FAIORD

Fairbanks

Thu 7/17

9:25 pm-8:40 am

1 stop8h 15m

Chicago O'Hare Intl

Sun 7/20

12:59 am-9:05 am

1 stop11h 06m

$634

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/1

Showing 1-10 of 26 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 $321). 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 July 3, 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 July 3, 2025.

The most flights from USAK to CHI are scheduled on a Thursday (12 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (5 on average).

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 July 3, 2025.
Peruse reviews from past customers who have flown with Alaska Airlines, Delta, and Hawaiian Airlines from Alaska to Chicago to help guide your decision. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Alaska Airlines
8.0
Very good
10,000 reviews

Overall

8.0

Comfort

7.8

Food

7.1

Crew

8.5

Boarding

8.1

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Alaska Airlines
8.0
Very good
10,000 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Overall

8.0

Comfort

7.8

Food

7.1

Crew

8.5

Boarding

8.1

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Delta
8.0
Very good
7,982 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Overall

8.0

Comfort

7.8

Food

7.1

Crew

8.5

Boarding

8.1

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Hawaiian Airlines
7.8
Good
2,545 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Overall

8.0

Comfort

7.8

Food

7.1

Crew

8.5

Boarding

8.1

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
United Airlines
7.4
Good
8,861 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Overall

8.0

Comfort

7.8

Food

7.1

Crew

8.5

Boarding

8.1

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
American Airlines
7.2
Good
10,000 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Overall

8.0

Comfort

7.8

Food

7.1

Crew

8.5

Boarding

8.1

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.

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 $173. However, be on the lookout for offers from Delta 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: United Airlines (93%), Air Canada (92%), Qatar Airways (91%).

  • What are the cheapest flights from Alaska to Chicago?

    Looking for the cheapest flight from Alaska to Chicago? While on average our users pay $1,080, our data indicates the cheapest price to be $234. The most popular route (Anchorage - Chicago O'Hare Intl), is priced around $352.

  • 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 $321). 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
Lansing
Benton Harbor
Porter
Hammond
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 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 July 3, 2025.
AirlineCheapestAverageFlexibilityOn-time
Hawaiian AirlinesCheapest$197Average$461FlexibilityNo cancel feeOn-time85%
DeltaCheapest$338Average$424FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$345Average$534FlexibilityNo cancel feeOn-time69%
Alaska AirlinesCheapest$354Average$669FlexibilityNo cancel feeOn-time75%
American AirlinesCheapest$358Average$517FlexibilityNo cancel feeOn-time71%

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