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$197+ 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 4/11. Fares are subject to change and may not be available on all flights or dates of travel.
ANC — CHI
Dec 27 — Jan 31
Fri 12/27
Fri 1/3
1 adult, Economy
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Cheap flight deals from Alaska to Chicago

Discover tips and strategies to find the most affordable flight options for your journey from Alaska (USAK) to Chicago (CHI). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated December 22, 2024.

Round-trip from

$405
(Alaska Airlines)

One-way from

$197
(Alaska Airlines)
From Alaska to Chicago (CHI)
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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 December 22, 2024.

This Alaska Airlines deal was found by Cheapflights users on 12/20. 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 12/247:15 amANC - ORD
2 stops25h 55mAlaska Airlines
Sat 1/116:55 pmORD - ANC
1 stop19h 20mAlaska Airlines
Deal found 12/20$615
This Delta deal was found by Cheapflights users on 12/20. 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 12/261:20 amANC - ORD
1 stop8h 55mDelta
Sat 1/117:15 amORD - ANC
1 stop11h 17mDelta
Deal found 12/20$750
This Delta deal was found by Cheapflights users on 12/20. 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 12/271:44 pmANC - MDW
2 stops16h 06mDelta
Sat 1/119:34 amMDW - ANC
2 stops14h 00mDelta
Deal found 12/20$1,010
This United Airlines deal was found by Cheapflights users on 12/20. 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 12/278:53 pmANC - ORD
Nonstop6h 27mUnited Airlines
Sat 1/115:50 pmORD - ANC
1 stop32h 07mUnited Airlines
Deal found 12/20$1,308
This United deal was found by Cheapflights users on 12/21. 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/268:53 pmANC - ORD
Nonstop6h 27mMultiple Airlines
Fri 12/271:10 pmORD - ANC
1 stop10h 38mMultiple Airlines
Deal found 12/21$1,497
This Alaska Airlines deal was found by Cheapflights users on 12/21. 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 12/217:00 amFAI - ORD
1 stop30h 50mAlaska Airlines
Sat 1/46:00 amORD - FAI
1 stop31h 50mAlaska Airlines
Deal found 12/21$2,392
This American Airlines deal was found by Cheapflights users on 12/20. 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.
Sun 12/221:59 amANC - ORD
1 stop14h 40mAmerican Airlines
Sat 1/117:00 amORD - ANC
2 stops14h 48mAmerican Airlines
Deal found 12/20$3,051

Find flights from Alaska to Chicago within your budget

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 December 22, 2024.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

AnchorageChicago

ANC - ORD

ANCORD

Anchorage

Fri 3/21

10:00 pm-7:40 am

Nonstop6h 40m

Chicago O'Hare Intl

Fri 3/28

7:16 pm-1:39 am

1 stop9h 23m

$405

AnchorageChicago

ANC - ORD

ANCORD

Anchorage

Mon 1/20

1:19 am-6:23 pm

2 stops14h 04m

Chicago O'Hare Intl

Tue 1/28

6:15 am-2:58 pm

2 stops11h 43m

$424

AnchorageChicago

ANC - ORD

ANCORD

Anchorage

Sun 1/19

11:59 pm-1:18 pm

1 stop10h 19m

Chicago O'Hare Intl

Sat 1/25

2:39 pm-10:57 pm

1 stop11h 18m

$460

AnchorageChicago

ANC - ORD

ANCORD

Anchorage

Fri 4/18

8:30 pm-9:27 am

1 stop9h 57m

Chicago O'Hare Intl

Mon 5/12

4:50 pm-8:18 pm

Nonstop6h 28m

$468

FairbanksChicago

FAI - ORD

FAIORD

Fairbanks

Sat 2/1

3:56 pm-1:07 pm

2 stops18h 11m

Chicago O'Hare Intl

Wed 2/5

6:55 pm-12:57 pm

2 stops21h 02m

$476

FairbanksChicago

FAI - ORD

FAIORD

Fairbanks

Fri 1/31

1:36 am-1:30 pm

1 stop8h 54m

Chicago O'Hare Intl

Wed 2/5

2:25 pm-12:31 am

1 stop13h 06m

$538

AnchorageChicago

ANC - MDW

ANCMDW

Anchorage

Mon 2/3

9:35 pm-9:35 am

1 stop9h 00m

Chicago Midway

Sun 2/16

9:33 am-12:15 am

2 stops17h 42m

$542

SitkaChicago

SIT - ORD

SITORD

Sitka

Sun 1/5

11:35 am-1:07 pm

2 stops22h 32m

Chicago O'Hare Intl

Thu 1/9

3:35 pm-6:18 pm

2 stops29h 43m

$780

AnchorageChicago

ANC - ORD

ANCORD

Anchorage

Sat 1/4

8:53 pm-6:20 am

Nonstop6h 27m

Chicago O'Hare Intl

Sat 1/11

8:21 pm-9:39 am

1 stop16h 18m

$1,443

AnchorageChicago

ANC - ORD

ANCORD

Anchorage

Fri 4/11

10:00 pm-7:40 am

Nonstop6h 40m

$197

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/22

Showing 1-10 of 17 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.

Travel insights for flights from Alaska to Chicago

Get recent, data-driven insights about flights from Alaska to Chicago including ideal travel times, pricing trends, and more.

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 $317). 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 December 22, 2024.

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 December 22, 2024.

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 December 22, 2024.
See what other customers who have flown with American Airlines, Alaska Airlines and Delta 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
9,537 reviews

Entertainment

7.1

Crew

8.5

Food

7.2

Overall

8.0

Comfort

7.9

Boarding

8.2

Reviews

1 / 10

Things were good, crew was good. It was just the flight itself was very rough. Lots of turbulence, probably one of the shakiest flights I've been on. Kids throwing up, kids crying everywhere because of it.

Alaska Airlines
8.0
Very good
9,537 reviews
Alaska Airlines
8.0
Very good
9,537 reviews

Entertainment

7.1

Crew

8.5

Food

7.2

Overall

8.0

Comfort

7.9

Boarding

8.2

Reviews

1 / 10

Things were good, crew was good. It was just the flight itself was very rough. Lots of turbulence, probably one of the shakiest flights I've been on. Kids throwing up, kids crying everywhere because of it.

Delta
8.0
Very good
8,594 reviews
Alaska Airlines
8.0
Very good
9,537 reviews

Entertainment

7.1

Crew

8.5

Food

7.2

Overall

8.0

Comfort

7.9

Boarding

8.2

Reviews

1 / 10

Things were good, crew was good. It was just the flight itself was very rough. Lots of turbulence, probably one of the shakiest flights I've been on. Kids throwing up, kids crying everywhere because of it.

United Airlines
7.4
Good
9,028 reviews
Alaska Airlines
8.0
Very good
9,537 reviews

Entertainment

7.1

Crew

8.5

Food

7.2

Overall

8.0

Comfort

7.9

Boarding

8.2

Reviews

1 / 10

Things were good, crew was good. It was just the flight itself was very rough. Lots of turbulence, probably one of the shakiest flights I've been on. Kids throwing up, kids crying everywhere because of it.

American Airlines
7.2
Good
10,000 reviews
Alaska Airlines
8.0
Very good
9,537 reviews

Entertainment

7.1

Crew

8.5

Food

7.2

Overall

8.0

Comfort

7.9

Boarding

8.2

Reviews

1 / 10

Things were good, crew was good. It was just the flight itself was very rough. Lots of turbulence, probably one of the shakiest flights I've been on. Kids throwing up, kids crying everywhere because of it.

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 $197. However, be on the lookout for offers from Delta and United 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: Qatar Airways (80%), Alaska Airlines (80%), Hawaiian Airlines (80%).

  • What are the cheapest flights from Alaska to Chicago?

    Looking for the cheapest flight from Alaska to Chicago? While on average our users pay $1,312, our data indicates the cheapest price to be $164. The most popular route (Anchorage - Chicago O'Hare Intl), is priced around $414.

  • 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 $317). 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

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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 December 22, 2024.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$195Average$460FlexibilityNo cancel feeOn-time71%
DeltaCheapest$293Average$460FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$326Average$584FlexibilityNo cancel feeOn-time69%
Alaska AirlinesCheapest$339Average$573FlexibilityNo cancel feeOn-time75%
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