HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Alaska

$180+ Cheap flights from Chicago (CHI) to Alaska

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 4/28. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — ANC
Dec 2 — Dec 91
Tue 12/2
Tue 12/9
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Chicago to Alaska 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 Chicago to Alaska

Keep the following information in mind while searching for Chicago to Alaska flight deals. Data was last updated November 2, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$338
(KAYAK)

One-way from

$180
(Delta)

Popular in

December

Cheapest in

April

Average price

$452

Good round-trip deal

$396 or less

Good one-way deal

$257 or less
Provider with most accurate pricing for Chicago (CHI)-Anchorage flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago (CHI)-Anchorage flights.
Search Deals
From Chicago (CHI) to Alaska
Search Deals
One-way flight from Chicago (CHI) to Alaska
Search Deals
High demand for flights, 0% potential price rise
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($12 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in November 2025
Search Deals
Price to beat on a round-trip flight from Chicago (CHI) to Alaska.
Search Deals
Price to beat on a one-way flight from Chicago (CHI) to Alaska.
Search Deals

Find flight deals from Chicago to Alaska

Cheapest flights from Chicago to Alaska
Explore the most affordable flight options available from Chicago to Alaska. Find the lowest fares from popular airlines and budget airlines, with prices last updated on November 2, 2025.

This Alaska Airlines deal was found by Cheapflights users on 10/31. 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 12/63:35 pmORD - ANC
1 stop12h 16mAlaska Airlines
Wed 12/242:20 amANC - ORD
1 stop11h 52mAlaska Airlines
Deal found 10/31$357
This Delta deal was found by Cheapflights users on 11/2. 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 12/216:45 amORD - ANC
1 stop15h 12mDelta
Wed 12/249:15 pmANC - ORD
1 stop11h 35mDelta
Deal found 11/2$358
This Delta deal was found by Cheapflights users on 11/1. 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 12/285:59 pmMDW - ANC
1 stop10h 23mDelta
Fri 1/169:15 pmANC - MDW
1 stop10h 50mDelta
Deal found 11/1$358
This Delta deal was found by Cheapflights users on 11/1. 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 12/32:30 pmORD - ANC
2 stops14h 24mDelta
Sat 12/612:30 amANC - ORD
1 stop10h 03mDelta
Deal found 11/1$363
This Delta deal was found by Cheapflights users on 11/1. 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 12/39:34 amMDW - ANC
2 stops16h 08mDelta
Sun 12/76:05 amANC - MDW
1 stop9h 13mDelta
Deal found 11/1$363
This Delta deal was found by Cheapflights users on 10/31. 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.
Sat 12/67:02 pmMDW - ANC
1 stop8h 55mDelta
Thu 12/251:44 pmANC - MDW
2 stops16h 05mDelta
Deal found 10/31$364
This Delta deal was found by Cheapflights users on 10/31. 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 11/219:41 amMDW - ANC
2 stops16h 08mDelta
Sun 11/305:37 pmANC - MDW
2 stops15h 57mDelta
Deal found 10/31$369
This Alaska Airlines deal was found by Cheapflights users on 11/1. 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 12/168:00 amORD - FAI
1 stop19h 39mAlaska Airlines
Fri 1/162:10 amFAI - ORD
1 stop9h 28mAlaska Airlines
Deal found 11/1$381
This Alaska Airlines deal was found by Cheapflights users on 11/1. 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 12/165:51 pmORD - FAI
1 stop9h 48mAlaska Airlines
Wed 1/141:52 pmFAI - ORD
2 stops24h 18mAlaska Airlines
Deal found 11/1$385
This Delta deal was found by Cheapflights users on 11/1. 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 12/166:00 amORD - FAI
2 stops21h 18mDelta
Mon 1/121:30 amFAI - ORD
1 stop19h 23mDelta
Deal found 11/1$386
This Alaska Airlines deal was found by Cheapflights users on 11/1. 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 12/173:35 pmORD - FAI
2 stops19h 04mAlaska Airlines
Wed 1/145:00 amFAI - ORD
2 stops15h 55mAlaska Airlines
Deal found 11/1$390
This Delta deal was found by Cheapflights users on 11/1. 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 12/1611:00 amORD - FAI
2 stops16h 18mDelta
Tue 1/131:30 amFAI - ORD
2 stops17h 22mDelta
Deal found 11/1$392

Cheapflights Fare Finder

 
Customize your flight search to find flights from Chicago to Alaska 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 November 2, 2025.
Use the filters below to find and compare flights from Chicago to Alaska that are best for you.

Fly from

Chicago

Fly to

Alaska

Route

Depart

Return

Price

ChicagoAnchorage

ORD - ANC

ORDANC

Chicago O'Hare Intl

Tue 4/7

7:00 am-2:14 pm

1 stop10h 14m

Anchorage

Mon 4/13

1:15 am-2:21 pm

1 stop10h 06m

$358

ChicagoAnchorage

ORD - ANC

ORDANC

Chicago O'Hare Intl

Mon 2/16

7:30 am-8:30 pm

1 stop16h 00m

Anchorage

Fri 2/20

9:55 pm-8:47 am

1 stop7h 52m

$358

ChicagoAnchorage

ORD - ANC

ORDANC

Chicago O'Hare Intl

Sat 12/20

6:35 am-6:49 pm

1 stop15h 14m

Anchorage

Wed 12/24

9:15 pm-11:50 am

1 stop11h 35m

$358

ChicagoAnchorage

ORD - ANC

ORDANC

Chicago O'Hare Intl

Fri 2/13

2:05 pm-8:45 pm

1 stop9h 40m

Anchorage

Sun 2/15

1:15 am-1:04 pm

1 stop8h 49m

$358

ChicagoAnchorage

ORD - ANC

ORDANC

Chicago O'Hare Intl

Mon 12/22

5:30 am-6:57 pm

1 stop16h 27m

Anchorage

Thu 12/25

1:15 am-1:20 pm

1 stop9h 05m

$358

ChicagoAnchorage

ORD - ANC

ORDANC

Chicago O'Hare Intl

Thu 2/19

2:00 pm-12:12 am

1 stop13h 12m

Anchorage

Sat 2/21

5:00 pm-5:04 am

1 stop9h 04m

$358

ChicagoAnchorage

ORD - ANC

ORDANC

Chicago O'Hare Intl

Thu 1/15

6:12 am-6:58 pm

1 stop15h 46m

Anchorage

Mon 1/19

9:15 pm-8:40 am

1 stop8h 25m

$358

ChicagoAnchorage

ORD - ANC

ORDANC

Chicago O'Hare Intl

Wed 12/3

5:40 pm-1:54 am

1 stop11h 14m

Anchorage

Sat 12/6

12:30 am-1:33 pm

1 stop10h 03m

$358

ChicagoAnchorage

ORD - ANC

ORDANC

Chicago O'Hare Intl

Thu 11/27

1:00 pm-6:46 pm

1 stop8h 46m

Anchorage

Thu 12/4

5:55 am-5:15 pm

1 stop8h 20m

$358

ChicagoAnchorage

ORD - ANC

ORDANC

Chicago O'Hare Intl

Wed 12/3

5:40 pm-1:54 am

1 stop11h 14m

Anchorage

Sat 12/13

5:55 am-5:18 pm

1 stop8h 23m

$358

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/1

Showing 1-10 of 52 results
1
2
3
...
6

Best time to book a flight from Chicago to Alaska

Have a flexible travel schedule? Discover the best time to fly to Alaska from Chicago 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 Chicago to Alaska

What is the cheapest month to book a flight from Chicago to Alaska?

Currently, November is the cheapest month in which you can book a flight from Chicago to Alaska (average of $168). Flying from Chicago to Alaska in July is currently the most expensive (average of $445). 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 CHI to AK?

Find hourly flight availability from Chicago to Alaska. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated November 2, 2025.

Unlike in the afternoon, when flights are generally more expensive, you can save up to 19% on flights from Chicago to Alaska by exploring options for tickets at noon.

What is the cheapest day to fly from Chicago to Alaska?

Use this chart to determine the cheapest time to fly round-trip from Chicago to Alaska. Price data was last updated on December 16, 2024.

Travelers seeking maximum savings on their Chicago to Alaska flight should consider departing on Friday at noon when fares are most often at their lowest. Sunday afternoons flights should be avoided if possible as fares are typically the most expensive at this time.

How much does it cost to fly round-trip from Chicago to Alaska?

Reviews of airlines servicing Alaska

Get insights into the airlines that provide service to Alaska. 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 Alaska. Reviews last updated November 2, 2025.
See what other customers who have flown with Alaska Airlines, Delta, and Hawaiian Airlines from Chicago to Alaska have to say. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Alaska Airlines
8.0
Very good
11,232 reviews

Boarding

8.1

Food

7.1

Comfort

7.8

Overall

8.0

Crew

8.5

Entertainment

7.0

Reviews

1 / 20
10.0
Excellent

Anonymous,Sep 2025

BOS - HNL

The flight was awesome but a little long. I would prefer a flight with a layover. The amount of space available was minimal and a little uncomfortable for that long of a flight.
Alaska Airlines
8.0
Very good
11,232 reviews
Alaska Airlines
8.0
Very good
11,232 reviews

Boarding

8.1

Food

7.1

Comfort

7.8

Overall

8.0

Crew

8.5

Entertainment

7.0

Reviews

1 / 20
10.0
Excellent

Anonymous,Sep 2025

BOS - HNL

The flight was awesome but a little long. I would prefer a flight with a layover. The amount of space available was minimal and a little uncomfortable for that long of a flight.
Delta
7.9
Good
7,997 reviews
Alaska Airlines
8.0
Very good
11,232 reviews

Boarding

8.1

Food

7.1

Comfort

7.8

Overall

8.0

Crew

8.5

Entertainment

7.0

Reviews

1 / 20
10.0
Excellent

Anonymous,Sep 2025

BOS - HNL

The flight was awesome but a little long. I would prefer a flight with a layover. The amount of space available was minimal and a little uncomfortable for that long of a flight.
Hawaiian Airlines
7.8
Good
2,799 reviews
Alaska Airlines
8.0
Very good
11,232 reviews

Boarding

8.1

Food

7.1

Comfort

7.8

Overall

8.0

Crew

8.5

Entertainment

7.0

Reviews

1 / 20
10.0
Excellent

Anonymous,Sep 2025

BOS - HNL

The flight was awesome but a little long. I would prefer a flight with a layover. The amount of space available was minimal and a little uncomfortable for that long of a flight.
United Airlines
7.4
Good
8,994 reviews
Alaska Airlines
8.0
Very good
11,232 reviews

Boarding

8.1

Food

7.1

Comfort

7.8

Overall

8.0

Crew

8.5

Entertainment

7.0

Reviews

1 / 20
10.0
Excellent

Anonymous,Sep 2025

BOS - HNL

The flight was awesome but a little long. I would prefer a flight with a layover. The amount of space available was minimal and a little uncomfortable for that long of a flight.
American Airlines
7.2
Good
11,033 reviews
Alaska Airlines
8.0
Very good
11,232 reviews

Boarding

8.1

Food

7.1

Comfort

7.8

Overall

8.0

Crew

8.5

Entertainment

7.0

Reviews

1 / 20
10.0
Excellent

Anonymous,Sep 2025

BOS - HNL

The flight was awesome but a little long. I would prefer a flight with a layover. The amount of space available was minimal and a little uncomfortable for that long of a flight.

Related info for your journey

Find useful and relevant information for your journey from Chicago to Alaska. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • How long is the flight from Chicago to Alaska?

    For as low as $358, Alaska Airlines can have you in Alaska from Chicago in 10h 14m. Airlines will cover a distance of 2837 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

  • What are the cheapest airlines to fly from Chicago to Alaska one-way?

    One-way options have recently been found by users for as low as $180 on Delta. Other airlines that offer cheap prices include American Airlines from $319 and Alaska Airlines from $334 one-way.

  • What are the most popular routes from Chicago to Alaska?

    When deciding which route to take from Chicago to Alaska consider Chicago O'Hare Intl - Anchorage, Chicago Midway - Anchorage or Chicago O'Hare Intl - Fairbanks as they are the most popular.

  • What are the most reliable airlines from Chicago to Alaska?

    Before booking your flight to Alaska from Chicago, check out the most reliable airlines to get you to your destination on time: Atlas Air (100%), Air Canada (85%), Lufthansa( 85%).

  • What are the cheapest flights from Chicago to Alaska?

    Looking at all options, your cheapest flight can be booked for $160. While the most popular route (Chicago O'Hare Intl - Anchorage) can be booked for $358 on average, our data indicates $402 when flying from Chicago to Alaska.

  • Can I find deals for flights from Chicago to Alaska that include hotel bookings?

    Yes. In addition to deals on Chicago to Alaska flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Chicago to Alaska?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Chicago to Alaska.

  • Can I find deals for business class flights from Chicago to Alaska?

    Yes. Cheapflights offers flight deals from Chicago to Alaska 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 Chicago to Alaska?

    Currently, November is the cheapest month in which you can book a flight from Chicago to Alaska (average of $168). Flying from Chicago to Alaska in July is currently the most expensive (average of $445). 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

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 Chicago to Alaska

See prices for flight routes from nearby airports that may be better suited for you.
O'Hare Intl to John F Kennedy Intl flights
O'Hare Intl to Dallas/Fort Worth flights
O'Hare Intl to Sky Harbor Intl flights
O'Hare Intl to Las Vegas flights
O'Hare Intl to LaGuardia flights
O'Hare Intl to Orlando flights
O'Hare Intl to Miami flights
O'Hare Intl to Newark flights
O'Hare Intl to Los Angeles flights
O'Hare Intl to Tampa flights
O'Hare Intl to San Francisco flights
O'Hare Intl to Denver flights
O'Hare Intl to Fort Lauderdale flights
O'Hare Intl to Seattle flights
O'Hare Intl to Atlanta flights
O'Hare Intl to Fort Myers flights
Midway to Dallas/Fort Worth flights
Midway to LaGuardia flights
Midway to John F Kennedy Intl flights
Midway to Las Vegas flights
O'Hare Intl to San Diego flights
O'Hare Intl to Honolulu flights
O'Hare Intl to New Orleans flights
Midway to Orlando flights
O'Hare Intl to Boston flights
O'Hare Intl to Reagan-National flights
O'Hare Intl to Philadelphia flights
O'Hare Intl to Hobby flights
Midway to Atlanta flights
O'Hare Intl to Nashville flights
O'Hare Intl to Dulles Intl flights
O'Hare Intl to Baltimore flights
O'Hare Intl to Santa Ana flights
O'Hare Intl to Salt Lake City flights
O'Hare Intl to West Palm Beach flights
Midway to Sky Harbor Intl flights
O'Hare Intl to Ontario flights
O'Hare Intl to George Bush Intcntl flights
O'Hare Intl to Austin flights
St. Louis to Las Vegas flights
O'Hare Intl to Sarasota flights
Midway to Denver flights
O'Hare Intl to Love Field flights
Midway to Miami flights
Midway to Tampa flights
St. Louis to LaGuardia flights
O'Hare Intl to Minneapolis flights
Midway to Fort Lauderdale flights
St. Louis to John F Kennedy Intl flights
O'Hare Intl to Palm Springs flights

Top 5 airlines flying from Chicago to Alaska

Discover the top 5 airlines that operate flights from Chicago to Alaska. 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 November 2, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$198Average$556FlexibilityNo cancel feeOn-timeN/A
Hawaiian AirlinesCheapest$227Average$526FlexibilityNo cancel feeOn-time85%
United AirlinesCheapest$318Average$727FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$318Average$665FlexibilityNo cancel feeOn-time71%
Alaska AirlinesCheapest$372Average$690FlexibilityNo cancel feeOn-time75%

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.