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$159+ 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 5/5. Fares are subject to change and may not be available on all flights or dates of travel.
ANC — CHI
Nov 19 — Nov 261
1 adult
Tue 11/19
Tue 11/26
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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 November 14, 2024.

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 November 14, 2024.

This Delta deal was found by Cheapflights users on 11/14. 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 12/55:15 pmANC - ORD
1 stop17h 00mDelta
Tue 12/102:10 pmORD - ANC
1 stop12h 28mDelta
Deal found 11/14$338
This Delta deal was found by Cheapflights users on 11/13. 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 12/912:45 amANC - MDW
2 stops13h 16mDelta
Fri 12/132:15 pmMDW - ANC
1 stop8h 37mDelta
Deal found 11/13$343
This Alaska Airlines deal was found by Cheapflights users on 11/13. 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 12/92:36 amANC - ORD
1 stop18h 11mAlaska Airlines
Sat 12/147:00 amORD - ANC
1 stop30h 04mAlaska Airlines
Deal found 11/13$398
This United Airlines deal was found by Cheapflights users on 11/14. 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 11/239:20 pmANC - ORD
Nonstop6h 01mUnited Airlines
Thu 12/59:36 pmORD - ANC
1 stop28h 17mUnited Airlines
Deal found 11/14$641

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 2,752,363 searches. Data last updated November 14, 2024.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

AnchorageChicago

ANC - ORD

ANCORD

Anchorage

Thu 12/5

5:15 pm-1:15 pm

1 stop17h 00m

Chicago O'Hare Intl

Wed 12/11

6:45 pm-1:41 am

1 stop9h 56m

$338

AnchorageChicago

ANC - MDW

ANCMDW

Anchorage

Mon 12/9

12:45 am-5:01 pm

2 stops13h 16m

Chicago Midway

Fri 12/13

2:15 pm-7:52 pm

1 stop8h 37m

$343

AnchorageChicago

ANC - ORD

ANCORD

Anchorage

Sat 4/12

8:43 pm-9:26 am

1 stop9h 43m

Chicago O'Hare Intl

Sat 5/10

4:50 pm-8:18 pm

Nonstop6h 28m

$370

AnchorageChicago

ANC - ORD

ANCORD

Anchorage

Sat 4/12

10:25 pm-7:42 am

Nonstop6h 17m

Chicago O'Hare Intl

Sat 5/10

10:00 am-11:24 pm

1 stop16h 24m

$385

AnchorageChicago

ANC - ORD

ANCORD

Anchorage

Thu 4/3

11:55 pm-10:25 pm

1 stop19h 30m

Chicago O'Hare Intl

Mon 4/7

4:07 pm-7:48 pm

Nonstop6h 41m

$502

AnchorageChicago

ANC - ORD

ANCORD

Anchorage

Mon 5/5

10:10 pm-7:25 am

Nonstop6h 15m

$159

AnchorageChicago

ANC - ORD

ANCORD

Anchorage

Tue 2/11

1:15 am-1:15 pm

1 stop9h 00m

$169

AnchorageChicago

ANC - ORD

ANCORD

Anchorage

Wed 2/12

1:49 am-4:58 pm

2 stops12h 09m

$174

AnchorageChicago

ANC - MDW

ANCMDW

Anchorage

Mon 12/9

9:13 pm-8:50 am

1 stop8h 37m

$174

AnchorageChicago

ANC - ORD

ANCORD

Anchorage

Sun 2/16

11:50 pm-11:20 am

1 stop8h 30m

$267

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/14

Showing 1-10 of 14 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, September is the cheapest month in which you can book a flight from Alaska to Chicago (average of $232). Flying from Alaska to Chicago in June is currently the most expensive (average of $308). 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 November 14, 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.

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 November 14, 2024.
See what other customers who have flown with Delta and Alaska 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
9,439 reviews

Boarding

8.2

Food

7.2

Comfort

7.9

Crew

8.6

Overall

8.0

Entertainment

7.1

Reviews

1 / 10

Service was good. We pre-ordered a snack but never made it to us.

Alaska Airlines
8.0
Very good
9,439 reviews
Alaska Airlines
8.0
Very good
9,439 reviews

Boarding

8.2

Food

7.2

Comfort

7.9

Crew

8.6

Overall

8.0

Entertainment

7.1

Reviews

1 / 10

Service was good. We pre-ordered a snack but never made it to us.

Delta
8.0
Very good
8,788 reviews
Alaska Airlines
8.0
Very good
9,439 reviews

Boarding

8.2

Food

7.2

Comfort

7.9

Crew

8.6

Overall

8.0

Entertainment

7.1

Reviews

1 / 10

Service was good. We pre-ordered a snack but never made it to us.

United Airlines
7.4
Good
9,194 reviews
Alaska Airlines
8.0
Very good
9,439 reviews

Boarding

8.2

Food

7.2

Comfort

7.9

Crew

8.6

Overall

8.0

Entertainment

7.1

Reviews

1 / 10

Service was good. We pre-ordered a snack but never made it to us.

American Airlines
7.2
Good
10,000 reviews
Alaska Airlines
8.0
Very good
9,439 reviews

Boarding

8.2

Food

7.2

Comfort

7.9

Crew

8.6

Overall

8.0

Entertainment

7.1

Reviews

1 / 10

Service was good. We pre-ordered a snack but never made it to us.

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 Delta, with whom users have recently found tickets for as low as $169. However, be on the lookout for offers from Alaska Airlines 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: American Airlines (100%), British Airways (100%), Air Canada (93%).

  • What are the cheapest flights from Alaska to Chicago?

    Looking for the cheapest flight from Alaska to Chicago? While on average our users pay $977, our data indicates the cheapest price to be $199. The most popular route (Anchorage - Chicago O'Hare Intl), is priced around $338.

  • 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, September is the cheapest month in which you can book a flight from Alaska to Chicago (average of $232). Flying from Alaska to Chicago in June is currently the most expensive (average of $308). 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 2,752,363 searches. Data last updated November 14, 2024.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$195Average$460FlexibilityNo cancel feeOn-time71%
DeltaCheapest$293Average$427FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$326Average$564FlexibilityNo cancel feeOn-time69%
Alaska AirlinesCheapest$331Average$630FlexibilityNo cancel feeOn-time75%
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