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$159+ Cheap flights from Alaska to Illinois

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 11/11. Fares are subject to change and may not be available on all flights or dates of travel.
ANC — ORD
Nov 13 — Nov 201
Thu 11/13
Thu 11/20
1 adult, Economy
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Find flight deals from Alaska to Illinois

Cheapest flights from Alaska to Illinois
Explore the most affordable flight options available from Alaska to Illinois. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 14, 2025.

This KAYAK deal was found by Cheapflights users on 10/12. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/119:05 amANC - ORD
1 stop9h 35mAlaska Airlines
Tue 11/183:25 pmORD - ANC
1 stop10h 23mAlaska Airlines
Deal found 10/12$318
This Trip.com deal was found by Cheapflights users on 10/12. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/264:10 pmANC - ORD
1 stop19h 43mAlaska Airlines
Wed 12/310:00 amORD - ANC
1 stop29h 50mAlaska Airlines
Deal found 10/12$331
This Alaska Airlines deal was found by Cheapflights users on 10/14. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/159:00 amANC - ORD
1 stop17h 01mAlaska Airlines
Sun 11/168:00 amORD - ANC
1 stop12h 22mAlaska Airlines
Deal found 10/14$332
This Delta deal was found by Cheapflights users on 10/14. 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.
Sun 11/96:00 amANC - ORD
1 stop8h 18mDelta
Sat 11/226:45 amORD - ANC
1 stop15h 49mDelta
Deal found 10/14$338
This Delta deal was found by Cheapflights users on 10/14. 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.
Tue 11/119:45 pmANC - MDW
1 stop8h 16mDelta
Tue 11/187:02 pmMDW - ANC
1 stop8h 54mDelta
Deal found 10/14$338
This Delta deal was found by Cheapflights users on 10/13. 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.
Wed 12/35:55 amANC - ORD
1 stop15h 04mDelta
Sun 12/710:45 amORD - ANC
2 stops18h 08mDelta
Deal found 10/13$343
This Delta deal was found by Cheapflights users on 10/14. 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.
Tue 11/1112:30 amANC - MDW
2 stops14h 48mDelta
Wed 11/199:41 amMDW - ANC
1 stop12h 05mDelta
Deal found 10/14$343
This United Airlines deal was found by Cheapflights users on 10/12. 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.
Tue 11/259:07 pmANC - ORD
Nonstop6h 02mUnited Airlines
Fri 11/284:05 pmORD - ANC
Nonstop6h 54mUnited Airlines
Deal found 10/12$368
This Delta deal was found by Cheapflights users on 10/13. 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.
Thu 12/45:55 amANC - STL
2 stops10h 15mDelta
Tue 12/910:45 amSTL - ANC
2 stops14h 57mDelta
Deal found 10/13$369
This Delta deal was found by Cheapflights users on 10/13. 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.
Sat 12/135:37 pmANC - ORD
2 stops15h 03mDelta
Wed 12/179:45 amORD - ANC
2 stops18h 16mDelta
Deal found 10/13$380
This Delta deal was found by Cheapflights users on 10/12. 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 11/269:45 pmANC - MDW
1 stop8h 16mDelta
Wed 12/31:14 pmMDW - ANC
2 stops15h 40mDelta
Deal found 10/12$383
This Delta deal was found by Cheapflights users on 10/13. 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.
Tue 11/256:05 amANC - MDW
1 stop9h 13mDelta
Fri 11/289:41 amMDW - ANC
1 stop12h 05mDelta
Deal found 10/13$410

Cheap flight deals from Alaska to Illinois

Keep the following information in mind while searching for Alaska to Illinois flight deals. Data was last updated October 14, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$313
(United Airlines)

One-way from

$159
(United Airlines)

Popular in

March

Cheapest in

October

Average price

$318

Good round-trip deal

$396 or less

Good one-way deal

$293 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 Illinois
Search Deals
One-way flight from Alaska to Illinois
Search Deals
Highest demand for flights based on searches. 17% potential increase in price ($108 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($16 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in October 2025
Search Deals
Price to beat on a round-trip flight from Alaska to Illinois.
Search Deals
Price to beat on a one-way flight from Alaska to Illinois.
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Alaska to Illinois 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 October 14, 2025.
Use the filters below to find and compare flights from Alaska to Illinois that are best for you.

Fly from

Alaska

Fly to

Illinois

Route

Depart

Return

Price

AnchorageChicago

ANC - ORD

ANCORD

Anchorage

Tue 4/7

12:00 pm-5:00 am

1 stop14h 00m

Chicago O'Hare Intl

Wed 4/8

7:00 am-8:25 pm

1 stop16h 25m

$332

AnchorageChicago

ANC - ORD

ANCORD

Anchorage

Wed 11/12

6:00 am-5:18 pm

1 stop8h 18m

Chicago O'Hare Intl

Sat 11/22

6:45 am-7:34 pm

1 stop15h 49m

$338

AnchorageChicago

ANC - ORD

ANCORD

Anchorage

Mon 11/10

4:30 pm-6:22 am

1 stop10h 52m

Chicago O'Hare Intl

Sun 11/16

7:00 am-1:32 pm

1 stop9h 32m

$338

AnchorageChicago

ANC - ORD

ANCORD

Anchorage

Tue 11/11

9:45 pm-8:30 am

1 stop7h 45m

Chicago O'Hare Intl

Tue 11/18

6:13 pm-1:57 am

1 stop10h 44m

$338

AnchorageChicago

ANC - ORD

ANCORD

Anchorage

Mon 11/10

10:00 am-9:40 pm

1 stop8h 40m

Chicago O'Hare Intl

Thu 11/20

3:25 pm-9:48 pm

1 stop9h 23m

$338

AnchorageChicago

ANC - ORD

ANCORD

Anchorage

Tue 11/4

12:30 am-1:30 pm

1 stop10h 00m

Chicago O'Hare Intl

Fri 12/12

6:10 pm-1:53 am

1 stop10h 43m

$338

AnchorageChicago

ANC - ORD

ANCORD

Anchorage

Sun 11/9

9:05 am-9:40 pm

1 stop9h 35m

Chicago O'Hare Intl

Thu 11/20

10:00 am-5:01 pm

1 stop10h 01m

$338

AnchorageChicago

ANC - ORD

ANCORD

Anchorage

Wed 12/3

5:55 am-11:59 pm

1 stop15h 04m

Chicago O'Hare Intl

Sun 12/7

6:10 pm-1:53 am

1 stop10h 43m

$338

AnchorageChicago

ANC - ORD

ANCORD

Anchorage

Thu 11/13

8:00 am-9:40 pm

1 stop10h 40m

Chicago O'Hare Intl

Sun 11/16

7:00 am-1:32 pm

1 stop9h 32m

$338

AnchorageChicago

ANC - ORD

ANCORD

Anchorage

Mon 2/9

1:20 am-1:25 pm

1 stop9h 05m

Chicago O'Hare Intl

Fri 2/13

9:30 am-7:10 pm

1 stop12h 40m

$338

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/12

Showing 1-10 of 53 results
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Best time to book a flight from Alaska to Illinois

Have a flexible travel schedule? Discover the best time to fly to Illinois 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 Illinois

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

Currently, May is the cheapest month in which you can book a flight from Alaska to Illinois (average of $187). Flying from Alaska to Illinois in July is currently the most expensive (average of $452). 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 IL?

Find hourly flight availability from Alaska to Illinois. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated October 14, 2025.

A simple way to save on the total cost of your ticket is to fly from Alaska to Illinois in the afternoon. If you’re flexible enough to do this you can expect to save up to 13% on your trip compared to booking a flight in the morning.

Weekly flight availability from Alaska to Illinois

Explore weekly flight availability from Alaska to Illinois. 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 October 14, 2025.

The most flights from USAK to USIL 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).

Reviews of airlines servicing Illinois

Get insights into the airlines that provide service to Illinois. 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 Illinois. Reviews last updated October 14, 2025.
Read reviews from past customers who have flown Alaska Airlines, Delta, and Hawaiian Airlines from Alaska to Illinois. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Alaska Airlines
8.0
Very good
11,069 reviews

Comfort

7.8

Overall

8.0

Crew

8.5

Entertainment

7.0

Boarding

8.1

Food

7.1

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
11,069 reviews
Alaska Airlines
8.0
Very good
11,069 reviews

Comfort

7.8

Overall

8.0

Crew

8.5

Entertainment

7.0

Boarding

8.1

Food

7.1

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
8.0
Very good
7,973 reviews
Alaska Airlines
8.0
Very good
11,069 reviews

Comfort

7.8

Overall

8.0

Crew

8.5

Entertainment

7.0

Boarding

8.1

Food

7.1

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
2,778 reviews
Alaska Airlines
8.0
Very good
11,069 reviews

Comfort

7.8

Overall

8.0

Crew

8.5

Entertainment

7.0

Boarding

8.1

Food

7.1

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
8,974 reviews
Alaska Airlines
8.0
Very good
11,069 reviews

Comfort

7.8

Overall

8.0

Crew

8.5

Entertainment

7.0

Boarding

8.1

Food

7.1

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
11,045 reviews
Alaska Airlines
8.0
Very good
11,069 reviews

Comfort

7.8

Overall

8.0

Crew

8.5

Entertainment

7.0

Boarding

8.1

Food

7.1

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 Alaska to Illinois. 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 Alaska to Illinois?

    A quick flight from Alaska to Illinois can take about 9h 13m. Alaska Airlines provides one of the quickest options available for as low as $338. Airlines will cover a distance of 2852 mi. This flight may include one or multiple stops.

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

    The cheapest airlines for a one-way flight from Alaska to Illinois are United Airlines ($159), Alaska Airlines ($168), and Delta ($168).

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

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

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

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

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

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

    Currently, May is the cheapest month in which you can book a flight from Alaska to Illinois (average of $187). Flying from Alaska to Illinois in July is currently the most expensive (average of $452). 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 Illinois

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Top 5 airlines flying from Alaska to Illinois

Discover the top 5 airlines that operate flights from Alaska to Illinois. 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 October 14, 2025.
AirlineCheapestAverageFlexibilityOn-time
Hawaiian AirlinesCheapest$187Average$461FlexibilityNo cancel feeOn-time85%
United AirlinesCheapest$254Average$484FlexibilityNo cancel feeOn-time69%
DeltaCheapest$259Average$427FlexibilityNo cancel feeOn-timeN/A
Alaska AirlinesCheapest$318Average$641FlexibilityNo cancel feeOn-time75%
American AirlinesCheapest$338Average$513FlexibilityNo cancel feeOn-time71%

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