HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Chicago

$185+ 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 6/15. Fares are subject to change and may not be available on all flights or dates of travel.
ANC — CHI
Mai 6 — Mai 131
Di 5/6
Di 5/13
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Alaska to Chicago with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

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 Mai 1, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$349
(SmartFares)

One-way from

$188
(Alaska Airlines)

Popular in

March

Cheapest in

November

Average price

$478

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.
Search Deals
Provider most trusted by Cheapflights users for Anchorage-Chicago (CHI) flights.
Search Deals
From Alaska to Chicago (CHI)
Search Deals
One-way flight from Alaska to Chicago (CHI)
Search Deals
Highest demand for flights based on searches. 15% potential increase in price ($93 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($13 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in May 2025
Search Deals
Price to beat on a round-trip flight from Alaska to Chicago (CHI).
Search Deals
Price to beat on a one-way flight from Alaska to Chicago (CHI).
Search Deals

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 Mai 1, 2025.

This SmartFares deal was found by Cheapflights users on 4/30. 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 SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fr 5/2310:36 pmANC - ORD
Nonstop6h 34mHawaiian Airlines
Do 5/299:30 amORD - ANC
Nonstop6h 30mHawaiian Airlines
Deal found 4/30$349
This Delta deal was found by Cheapflights users on 4/30. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fr 5/2310:00 pmANC - ORD
1 stop11h 41mDelta
Do 5/292:25 pmORD - ANC
1 stop12h 00mDelta
Deal found 4/30$396
This Kiwi.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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fr 6/67:00 amANC - ORD
2 stops13h 56mMultiple Airlines
Sa 6/1412:59 amORD - ANC
Nonstop6h 38mMultiple Airlines
Deal found 4/28$399
This Alaska Airlines deal was found by Cheapflights users on 4/29. 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.
Do 5/295:05 amANC - ORD
2 stops15h 54mAlaska Airlines
Do 6/59:30 amORD - ANC
Nonstop6h 30mAlaska Airlines
Deal found 4/29$406
This Delta deal was found by Cheapflights users on 4/29. 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.
Fr 5/239:59 pmANC - MDW
1 stop7h 37mDelta
Mo 5/269:16 amMDW - ANC
1 stop14h 29mDelta
Deal found 4/29$429
This Alaska Airlines deal was found by Cheapflights users on 4/30. 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.
Mo 6/21:44 amFAI - ORD
1 stop17h 39mAlaska Airlines
Fr 6/67:51 pmORD - FAI
2 stops17h 32mAlaska Airlines
Deal found 4/30$495
This American Airlines deal was found by Cheapflights users on 4/29. 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.
Do 5/299:48 pmANC - ORD
Nonstop6h 16mAmerican Airlines
So 6/15:10 pmORD - ANC
Nonstop6h 37mAmerican Airlines
Deal found 4/29$496
This Delta deal was found by Cheapflights users on 4/30. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Di 5/271:45 amFAI - ORD
1 stop12h 40mDelta
Mi 6/41:40 pmORD - FAI
2 stops13h 48mDelta
Deal found 4/30$509
This Hawaiian Airlines deal was found by Cheapflights users on 4/30. 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 Hawaiian Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Di 5/271:44 amFAI - ORD
1 stop9h 34mHawaiian Airlines
Mi 6/47:51 pmORD - FAI
1 stop9h 29mHawaiian Airlines
Deal found 4/30$534
This United Airlines deal was found by Cheapflights users on 4/29. 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.
Mi 10/88:57 pmANC - ORD
Nonstop6h 12mUnited Airlines
Mo 10/134:07 pmORD - ANC
Nonstop6h 41mUnited Airlines
Deal found 4/29$552
This United Airlines deal was found by Cheapflights users on 4/30. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mo 7/2811:00 pmFAI - ORD
1 stop9h 25mUnited Airlines
Mi 8/134:15 pmORD - FAI
Nonstop6h 35mUnited Airlines
Deal found 4/30$864
This American Airlines deal was found by Cheapflights users on 4/30. 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.
Mi 5/141:44 amFAI - ORD
1 stop15h 46mAmerican Airlines
Mo 5/197:35 amORD - FAI
1 stop19h 49mAmerican Airlines
Deal found 4/30$867

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 Mai 1, 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

Fr 5/23

10:36 pm-8:10 am

Nonstop6h 34m

Chicago O'Hare Intl

Do 5/29

9:30 am-1:00 pm

Nonstop6h 30m

$349

AnchorageChicago

ANC - ORD

ANCORD

Anchorage

Fr 5/23

10:00 pm-12:41 pm

1 stop11h 41m

Chicago O'Hare Intl

Do 5/29

2:25 pm-11:25 pm

1 stop12h 00m

$396

AnchorageChicago

ANC - ORD

ANCORD

Anchorage

Fr 6/6

7:00 am-11:56 pm

2 stops13h 56m

Chicago O'Hare Intl

Sa 6/14

12:59 am-4:37 am

Nonstop6h 38m

$399

AnchorageChicago

ANC - ORD

ANCORD

Anchorage

Do 5/29

5:05 am-11:59 pm

2 stops15h 54m

Chicago O'Hare Intl

Do 6/5

9:30 am-1:00 pm

Nonstop6h 30m

$406

AnchorageChicago

ANC - MDW

ANCMDW

Anchorage

Fr 5/23

9:59 pm-8:36 am

1 stop7h 37m

Chicago Midway

Mo 5/26

9:16 am-8:45 pm

1 stop14h 29m

$429

FairbanksChicago

FAI - ORD

FAIORD

Fairbanks

Mo 6/2

1:44 am-10:23 pm

1 stop17h 39m

Chicago O'Hare Intl

Fr 6/6

7:51 pm-10:23 am

2 stops17h 32m

$495

AnchorageChicago

ANC - ORD

ANCORD

Anchorage

Do 5/29

9:48 pm-7:04 am

Nonstop6h 16m

Chicago O'Hare Intl

So 6/1

5:10 pm-8:47 pm

Nonstop6h 37m

$496

FairbanksChicago

FAI - ORD

FAIORD

Fairbanks

Di 5/27

1:45 am-5:25 pm

1 stop12h 40m

Chicago O'Hare Intl

Mi 6/4

1:40 pm-12:28 am

2 stops13h 48m

$509

FairbanksChicago

FAI - ORD

FAIORD

Fairbanks

Di 5/27

1:44 am-2:18 pm

1 stop9h 34m

Chicago O'Hare Intl

Mi 6/4

7:51 pm-2:20 am

1 stop9h 29m

$534

AnchorageChicago

ANC - ORD

ANCORD

Anchorage

Sa 5/24

8:34 pm-5:51 am

Nonstop6h 17m

Chicago O'Hare Intl

Fr 6/20

9:30 am-1:22 pm

Nonstop6h 52m

$564

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/29

Showing 1-10 of 27 results
1
2
3

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 Mai 1, 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 Mai 1, 2025.

The most flights from USAK to CHI are scheduled on a Wednesday (4 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 Mai 1, 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
9,972 reviews

Entertainment

7.1

Comfort

7.9

Boarding

8.1

Food

7.1

Overall

8.0

Crew

8.5

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
9,972 reviews
Alaska Airlines
8.0
Very good
9,972 reviews

Entertainment

7.1

Comfort

7.9

Boarding

8.1

Food

7.1

Overall

8.0

Crew

8.5

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
7,934 reviews
Alaska Airlines
8.0
Very good
9,972 reviews

Entertainment

7.1

Comfort

7.9

Boarding

8.1

Food

7.1

Overall

8.0

Crew

8.5

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
2,408 reviews
Alaska Airlines
8.0
Very good
9,972 reviews

Entertainment

7.1

Comfort

7.9

Boarding

8.1

Food

7.1

Overall

8.0

Crew

8.5

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
9,972 reviews

Entertainment

7.1

Comfort

7.9

Boarding

8.1

Food

7.1

Overall

8.0

Crew

8.5

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
9,972 reviews

Entertainment

7.1

Comfort

7.9

Boarding

8.1

Food

7.1

Overall

8.0

Crew

8.5

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 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: 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

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Alaska to Chicago

See prices for flight routes from nearby airports that may be better suited for you.
LaGuardia to O'Hare Intl flights
Dallas/Fort Worth to O'Hare Intl flights
John F Kennedy Intl to O'Hare Intl flights
Newark to O'Hare Intl flights
John F Kennedy Intl to Midway flights
Newark to Midway flights
Los Angeles to O'Hare Intl flights
Boston to O'Hare Intl flights
Dallas/Fort Worth to Midway flights
Baltimore to O'Hare Intl flights
Philadelphia to O'Hare Intl flights
Reagan-National to O'Hare Intl flights
San Francisco to O'Hare Intl flights
Seattle to O'Hare Intl flights
Dulles Intl to O'Hare Intl flights
Ontario to O'Hare Intl flights
Sky Harbor Intl to O'Hare Intl flights
LaGuardia to Midway flights
Denver to O'Hare Intl flights
San Francisco to Midway flights
Santa Ana to O'Hare Intl flights
Raleigh to O'Hare Intl flights
San Diego to O'Hare Intl flights
Orlando to O'Hare Intl flights
Austin to O'Hare Intl flights
Atlanta to O'Hare Intl flights
Burbank to O'Hare Intl flights
Hobby to O'Hare Intl flights
Dulles Intl to Midway flights
George Bush Intcntl to O'Hare Intl flights
Atlanta to Midway flights
Fort Lauderdale to O'Hare Intl flights
Portland to O'Hare Intl flights
Tampa to O'Hare Intl flights
Hartford to O'Hare Intl flights
Charlotte to O'Hare Intl flights
Los Angeles to Midway flights
Miami to O'Hare Intl flights
Boston to Midway flights
Baltimore to Midway flights
Newark to St. Louis flights
Reagan-National to Midway flights
Hobby to Midway flights
Minneapolis to O'Hare Intl flights
Oakland to O'Hare Intl flights
San Jose to O'Hare Intl flights
Tampa to Midway flights
LaGuardia to St. Louis flights
Minneapolis to Midway flights
Seattle to St. Louis flights

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 Mai 1, 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%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.