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$188+ 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 5/23. Fares are subject to change and may not be available on all flights or dates of travel.
ANC — CHI
May 4 — May 111
Sun 5/4
Sun 5/11
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 29, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$386
(Alaska Airlines)

One-way from

$188
(Alaska Airlines)

Popular in

March

Cheapest in

November

Average price

$596

Good round-trip deal

$270 or less

Good one-way deal

$260 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. 15% potential increase in price ($93 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 29, 2025.

This Hawaiian Airlines deal was found by Cheapflights users on 4/28. 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 Hawaiian Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/710:36 pmANC - ORD
Nonstop6h 34mHawaiian Airlines
Fri 6/1312:59 amORD - ANC
Nonstop6h 38mHawaiian Airlines
Deal found 4/28$386
This Delta deal was found by Cheapflights users on 4/28. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/239:59 pmANC - ORD
1 stop10h 48mDelta
Mon 5/267:15 amORD - ANC
1 stop12h 05mDelta
Deal found 4/28$396
This Alaska Airlines deal was found by Cheapflights users on 4/28. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/2710:36 pmANC - ORD
Nonstop6h 34mAlaska Airlines
Tue 6/39:30 amORD - ANC
Nonstop6h 30mAlaska Airlines
Deal found 4/28$416
This Delta deal was found by Cheapflights users on 4/28. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/239:59 pmANC - MDW
1 stop7h 37mDelta
Mon 5/269:16 amMDW - ANC
1 stop14h 29mDelta
Deal found 4/28$457
This American Airlines deal was found by Cheapflights users on 4/28. 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.
Thu 7/109:47 pmANC - ORD
Nonstop6h 22mAmerican Airlines
Sun 7/135:06 pmORD - ANC
Nonstop6h 36mAmerican Airlines
Deal found 4/28$485
This Delta deal was found by Cheapflights users on 4/28. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/201:45 amFAI - ORD
1 stop8h 45mDelta
Wed 5/281:40 pmORD - FAI
2 stops13h 48mDelta
Deal found 4/28$524
This Booking.com deal was found by Cheapflights users on 4/28. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/178:55 pmANC - ORD
1 stop14h 10mSun Country Air
Sun 7/202:30 pmORD - ANC
1 stop8h 18mSun Country Air
Deal found 4/28$543
This United Airlines deal was found by Cheapflights users on 4/28. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/1711:59 pmANC - ORD
Nonstop6h 20mUnited Airlines
Thu 5/292:33 pmORD - ANC
1 stop11h 19mUnited Airlines
Deal found 4/28$547
This Mytrip deal was found by Cheapflights users on 4/28. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/171:20 pmANC - ORD
1 stop25h 07mMultiple Airlines
Thu 5/294:35 pmORD - ANC
3 stops46h 43mMultiple Airlines
Deal found 4/28$562
This Alaska Airlines deal was found by Cheapflights users on 4/28. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/69:25 pmFAI - ORD
1 stop8h 15mAlaska Airlines
Wed 8/132:03 pmORD - FAI
1 stop13h 26mAlaska Airlines
Deal found 4/28$601
This Hawaiian Airlines deal was found by Cheapflights users on 4/28. 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 Hawaiian Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/67:59 pmFAI - ORD
1 stop9h 41mHawaiian Airlines
Tue 8/1212:59 amORD - FAI
1 stop11h 06mHawaiian Airlines
Deal found 4/28$614
This United Airlines deal was found by Cheapflights users on 4/28. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/68:53 pmFAI - ORD
Nonstop6h 04mUnited Airlines
Wed 8/134:15 pmORD - FAI
Nonstop6h 35mUnited Airlines
Deal found 4/28$862

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 29, 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

Sat 6/7

10:36 pm-8:10 am

Nonstop6h 34m

Chicago O'Hare Intl

Fri 6/13

12:59 am-4:37 am

Nonstop6h 38m

$386

AnchorageChicago

ANC - ORD

ANCORD

Anchorage

Fri 5/23

9:59 pm-11:47 am

1 stop10h 48m

Chicago O'Hare Intl

Mon 5/26

7:15 am-4:20 pm

1 stop12h 05m

$396

AnchorageChicago

ANC - ORD

ANCORD

Anchorage

Tue 5/27

10:36 pm-8:10 am

Nonstop6h 34m

Chicago O'Hare Intl

Tue 6/3

9:30 am-1:00 pm

Nonstop6h 30m

$416

AnchorageChicago

ANC - MDW

ANCMDW

Anchorage

Fri 5/23

9:59 pm-8:36 am

1 stop7h 37m

Chicago Midway

Mon 5/26

9:16 am-8:45 pm

1 stop14h 29m

$457

AnchorageChicago

ANC - ORD

ANCORD

Anchorage

Thu 7/10

9:47 pm-7:09 am

Nonstop6h 22m

Chicago O'Hare Intl

Sun 7/13

5:06 pm-8:42 pm

Nonstop6h 36m

$485

FairbanksChicago

FAI - ORD

FAIORD

Fairbanks

Tue 5/20

1:45 am-1:30 pm

1 stop8h 45m

Chicago O'Hare Intl

Wed 5/28

1:40 pm-12:28 am

2 stops13h 48m

$524

AnchorageChicago

ANC - ORD

ANCORD

Anchorage

Thu 7/17

8:55 pm-2:05 pm

1 stop14h 10m

Chicago O'Hare Intl

Sun 7/20

2:30 pm-7:48 pm

1 stop8h 18m

$543

AnchorageChicago

ANC - ORD

ANCORD

Anchorage

Sat 5/17

11:59 pm-9:19 am

Nonstop6h 20m

Chicago O'Hare Intl

Thu 5/29

2:33 pm-10:52 pm

1 stop11h 19m

$547

AnchorageChicago

ANC - ORD

ANCORD

Anchorage

Sat 5/17

1:20 pm-5:27 pm

1 stop25h 07m

Chicago O'Hare Intl

Thu 5/29

4:35 pm-12:18 pm

3 stops46h 43m

$562

FairbanksChicago

FAI - ORD

FAIORD

Fairbanks

Wed 8/6

9:25 pm-8:40 am

1 stop8h 15m

Chicago O'Hare Intl

Wed 8/13

2:03 pm-12:29 am

1 stop13h 26m

$601

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/28

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 $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 April 29, 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 29, 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 29, 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
9,949 reviews

Overall

8.0

Crew

8.5

Entertainment

7.1

Boarding

8.2

Food

7.1

Comfort

7.9

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
9,949 reviews
Alaska Airlines
8.0
Very good
9,949 reviews

Overall

8.0

Crew

8.5

Entertainment

7.1

Boarding

8.2

Food

7.1

Comfort

7.9

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
7,929 reviews
Alaska Airlines
8.0
Very good
9,949 reviews

Overall

8.0

Crew

8.5

Entertainment

7.1

Boarding

8.2

Food

7.1

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Hawaiian Airlines
7.9
Good
2,402 reviews
Alaska Airlines
8.0
Very good
9,949 reviews

Overall

8.0

Crew

8.5

Entertainment

7.1

Boarding

8.2

Food

7.1

Comfort

7.9

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
8,696 reviews
Alaska Airlines
8.0
Very good
9,949 reviews

Overall

8.0

Crew

8.5

Entertainment

7.1

Boarding

8.2

Food

7.1

Comfort

7.9

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
9,949 reviews

Overall

8.0

Crew

8.5

Entertainment

7.1

Boarding

8.2

Food

7.1

Comfort

7.9

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 Alaska Airlines, with whom users have recently found tickets for as low as $188. However, be on the lookout for offers from Delta and Sun Country Air, 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%), Hawaiian Airlines (100%).

  • What are the cheapest flights from Alaska to Chicago?

    Looking for the cheapest flight from Alaska to Chicago? While on average our users pay $1,144, our data indicates the cheapest price to be $189. 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 $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
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 29, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$270Average$418FlexibilityNo cancel feeOn-timeN/A
Alaska AirlinesCheapest$339Average$658FlexibilityNo cancel feeOn-time75%
United AirlinesCheapest$345Average$495FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$392Average$467FlexibilityNo cancel feeOn-time71%

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