Chicago

$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 3/23. Fares are subject to change and may not be available on all flights or dates of travel.
ANC — CHI
Jan 26 — Feb 21
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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 January 21, 2025.

Round-trip from

$376
(Alaska Airlines)

One-way from

$188
(Alaska Airlines)

Good round-trip deal

$536 or less

Good one-way deal

$275 or less
From Alaska to Chicago (CHI)
One-way flight from Alaska to Chicago (CHI)
Price to beat on a round-trip flight from Alaska to Chicago (CHI).
Price to beat on a one-way flight from Alaska to Chicago (CHI).

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 January 21, 2025.

This Alaska Airlines deal was found by Cheapflights users on 1/21. 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.
Sun 4/2010:00 pmANC - ORD
Nonstop6h 40mAlaska Airlines
Sat 4/266:50 pmORD - ANC
Nonstop6h 34mAlaska Airlines
Deal found 1/21$376
This Delta deal was found by Cheapflights users on 1/21. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/226:00 amANC - ORD
1 stop14h 53mDelta
Sat 4/267:30 amORD - ANC
1 stop19h 29mDelta
Deal found 1/21$396
This Delta deal was found by Cheapflights users on 1/21. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/2212:40 amANC - MDW
2 stops13h 23mDelta
Tue 4/291:16 pmMDW - ANC
1 stop9h 17mDelta
Deal found 1/21$401
This United Airlines deal was found by Cheapflights users on 1/20. 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.
Sun 5/411:44 pmANC - ORD
1 stop10h 31mUnited Airlines
Fri 5/91:05 pmORD - ANC
Nonstop6h 39mUnited Airlines
Deal found 1/20$407
This Alaska Airlines deal was found by Cheapflights users on 1/21. 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.
Tue 2/117:00 amFAI - ORD
1 stop13h 59mAlaska Airlines
Tue 2/182:00 pmORD - FAI
1 stop15h 22mAlaska Airlines
Deal found 1/21$566
This American Airlines deal was found by Cheapflights users on 1/20. 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.
Sat 5/31:31 amANC - ORD
1 stop12h 53mAmerican Airlines
Fri 5/94:50 pmORD - ANC
Nonstop6h 28mAmerican Airlines
Deal found 1/20$571
This Delta deal was found by Cheapflights users on 1/21. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/161:30 amFAI - ORD
1 stop8h 54mDelta
Mon 7/211:35 pmORD - FAI
2 stops13h 28mDelta
Deal found 1/21$572
This Kiwi.com deal was found by Cheapflights users on 1/20. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/217:18 pmANC - ORD
1 stop16h 51mMultiple Airlines
Sun 3/24:05 pmORD - ANC
1 stop11h 24mMultiple Airlines
Deal found 1/20$578
This Delta deal was found by Cheapflights users on 1/21. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 2/91:36 amFAI - MDW
2 stops13h 07mDelta
Tue 2/181:26 pmMDW - FAI
2 stops14h 08mDelta
Deal found 1/21$620
This American Airlines deal was found by Cheapflights users on 1/21. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/175:10 pmFAI - ORD
1 stop10h 50mAmerican Airlines
Mon 7/211:46 pmORD - FAI
1 stop12h 09mAmerican Airlines
Deal found 1/21$736
This United deal was found by Cheapflights users on 1/21. 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 7/178:59 pmFAI - ORD
Nonstop5h 58mUnited Airlines
Mon 7/215:00 amORD - FAI
1 stop17h 39mUnited Airlines
Deal found 1/21$767

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 January 21, 2025.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

AnchorageChicago

ANC - ORD

ANCORD

Anchorage

Sun 4/20

10:00 pm-7:40 am

Nonstop6h 40m

Chicago O'Hare Intl

Sat 4/26

6:50 pm-10:24 pm

Nonstop6h 34m

$376

AnchorageChicago

ANC - ORD

ANCORD

Anchorage

Mon 4/21

12:40 am-5:54 pm

1 stop14h 14m

Chicago O'Hare Intl

Sat 4/26

7:30 am-2:45 pm

1 stop10h 15m

$396

AnchorageChicago

ANC - MDW

ANCMDW

Anchorage

Tue 4/22

12:40 am-5:03 pm

2 stops13h 23m

Chicago Midway

Tue 4/29

1:16 pm-7:33 pm

1 stop9h 17m

$401

AnchorageChicago

ANC - ORD

ANCORD

Anchorage

Thu 4/3

8:30 pm-5:50 am

Nonstop6h 20m

Chicago O'Hare Intl

Mon 4/7

3:40 pm-7:21 pm

Nonstop6h 41m

$456

FairbanksChicago

FAI - ORD

FAIORD

Fairbanks

Tue 2/11

7:00 am-11:59 pm

1 stop13h 59m

Chicago O'Hare Intl

Tue 2/18

2:00 pm-2:22 am

1 stop15h 22m

$566

FairbanksChicago

FAI - ORD

FAIORD

Fairbanks

Wed 7/16

1:30 am-1:24 pm

1 stop8h 54m

Chicago O'Hare Intl

Mon 7/21

1:35 pm-12:03 am

2 stops13h 28m

$572

AnchorageChicago

ANC - ORD

ANCORD

Anchorage

Fri 2/21

7:18 pm-3:09 pm

1 stop16h 51m

Chicago O'Hare Intl

Sun 3/2

4:05 pm-12:29 am

1 stop11h 24m

$578

FairbanksChicago

FAI - MDW

FAIMDW

Fairbanks

Sun 2/9

1:36 am-5:43 pm

2 stops13h 07m

Chicago Midway

Tue 2/18

1:26 pm-12:34 am

2 stops14h 08m

$620

FairbanksChicago

FAI - ORD

FAIORD

Fairbanks

Thu 7/17

5:10 pm-7:00 am

1 stop10h 50m

Chicago O'Hare Intl

Mon 7/21

1:46 pm-10:55 pm

1 stop12h 09m

$736

FairbanksChicago

FAI - ORD

FAIORD

Fairbanks

Thu 7/17

8:59 pm-5:57 am

Nonstop5h 58m

Chicago O'Hare Intl

Mon 7/21

5:00 am-7:39 pm

1 stop17h 39m

$767

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/20

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 $320). 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 January 21, 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.

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 January 21, 2025.
See what other customers who have flown with Alaska Airlines, Delta and United 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.
8.0
Very good
9,706 reviews

Entertainment

7.1

Food

7.1

Boarding

8.2

Crew

8.5

Overall

8.0

Comfort

7.9

Reviews

1 / 10

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

8.0
Very good
9,706 reviews
8.0
Very good
9,706 reviews

Entertainment

7.1

Food

7.1

Boarding

8.2

Crew

8.5

Overall

8.0

Comfort

7.9

Reviews

1 / 10

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

8.0
Very good
8,521 reviews
8.0
Very good
9,706 reviews

Entertainment

7.1

Food

7.1

Boarding

8.2

Crew

8.5

Overall

8.0

Comfort

7.9

Reviews

1 / 10

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

7.4
Good
8,984 reviews
8.0
Very good
9,706 reviews

Entertainment

7.1

Food

7.1

Boarding

8.2

Crew

8.5

Overall

8.0

Comfort

7.9

Reviews

1 / 10

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

7.2
Good
10,000 reviews
8.0
Very good
9,706 reviews

Entertainment

7.1

Food

7.1

Boarding

8.2

Crew

8.5

Overall

8.0

Comfort

7.9

Reviews

1 / 10

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 Alaska Airlines, with whom users have recently found tickets for as low as $188. 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?

  • 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: Air Canada (82%), Korean Air (62%), United Airlines (61%).

  • What are the cheapest flights from Alaska to Chicago?

    Looking for the cheapest flight from Alaska to Chicago? While on average our users pay $1,030, our data indicates the cheapest price to be $212. The most popular route (Anchorage - Chicago O'Hare Intl), is priced around $401.

  • 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 $320). 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

Browse thousands of different options on Cheapflights for your next trip

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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.

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 January 21, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$195Average$460FlexibilityNo cancel feeOn-time71%
DeltaCheapest$293Average$474FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$326Average$585FlexibilityNo cancel feeOn-time69%
Alaska AirlinesCheapest$339Average$594FlexibilityNo cancel feeOn-time75%
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