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$169+ 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 7/9. Fares are subject to change and may not be available on all flights or dates of travel.
ANC — ORD
Feb 13 — Feb 201
Fri 2/13
Fri 2/20
1 adult, Economy
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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 January 14, 2026.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$346
(Trip.com)

One-way from

$169
(Alaska Airlines)

Popular in

March

Cheapest in

October

Average price

$557

Good round-trip deal

$594 or less

Good one-way deal

$294 or less
Provider with most accurate pricing for Anchorage-Chicago (CHI) flight deals.
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Provider most trusted by Cheapflights users for Anchorage-Chicago (CHI) flights.
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From Alaska to Illinois
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One-way flight from Alaska to Illinois
Search Deals
Highest demand for flights based on searches. 25% potential increase in price ($168 potential increase over avg. RT price).
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Cheapest flight prices on average. 6% potential price decrease ($29 potential savings vs. average RT price).
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Average for round-trip flights in January 2026
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Price to beat on a round-trip flight from Alaska to Illinois.
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Price to beat on a one-way flight from Alaska to Illinois.
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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 January 14, 2026.

This Alaska Airlines deal was found by Cheapflights users on 1/13. 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 8/249:08 pm
ANC
-
ORD
Nonstop6h 18m
Alaska Airlines
Fri 8/287:00 am
ORD
-
ANC
1 stop16h 36m
Alaska Airlines
Deal found 1/13$349
This Alaska Airlines deal was found by Cheapflights users on 1/13. 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 4/2012:10 pm
ANC
-
ORD
1 stop8h 49m
Alaska Airlines
Thu 4/305:52 pm
ORD
-
ANC
1 stop10h 44m
Alaska Airlines
Deal found 1/13$359
This Alaska Airlines deal was found by Cheapflights users on 1/12. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/135:00 am
ANC
-
ORD
1 stop29h 11m
Alaska Airlines
Tue 2/247:00 am
ORD
-
ANC
1 stop17h 49m
Alaska Airlines
Deal found 1/12$362
This Alaska Airlines deal was found by Cheapflights users on 1/12. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/710:26 am
ANC
-
ORD
1 stop10h 33m
Alaska Airlines
Wed 5/133:43 pm
ORD
-
ANC
2 stops13h 16m
Alaska Airlines
Deal found 1/12$364
This Alaska Airlines deal was found by Cheapflights users on 1/11. 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.
Fri 2/138:55 am
ANC
-
ORD
1 stop25h 16m
Alaska Airlines
Tue 2/172:07 pm
ORD
-
ANC
2 stops23h 12m
Alaska Airlines
Deal found 1/11$367
This United Airlines deal was found by Cheapflights users on 1/13. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/239:04 pm
ANC
-
ORD
Nonstop6h 16m
United Airlines
Thu 4/304:05 pm
ORD
-
ANC
Nonstop6h 40m
United Airlines
Deal found 1/13$377
This Delta deal was found by Cheapflights users on 1/13. 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 2/59:13 pm
ANC
-
ORD
1 stop15h 06m
Delta
Sun 2/86:15 am
ORD
-
ANC
1 stop15h 41m
Delta
Deal found 1/13$379
This Delta deal was found by Cheapflights users on 1/13. 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.
Sun 2/89:15 pm
ANC
-
MDW
1 stop8h 53m
Delta
Tue 2/109:53 am
MDW
-
ANC
1 stop12h 03m
Delta
Deal found 1/13$379
This Delta deal was found by Cheapflights users on 1/13. 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 8/249:55 pm
ANC
-
ORD
1 stop14h 03m
Delta
Fri 8/281:35 pm
ORD
-
ANC
2 stops13h 58m
Delta
Deal found 1/13$384
This Delta deal was found by Cheapflights users on 1/13. 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 8/249:55 pm
ANC
-
MDW
1 stop12h 12m
Delta
Fri 8/281:00 pm
MDW
-
ANC
2 stops14h 33m
Delta
Deal found 1/13$384
This United Airlines deal was found by Cheapflights users on 1/14. 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.
Fri 3/1311:52 pm
ANC
-
ORD
1 stop8h 27m
United Airlines
Fri 3/204:10 pm
ORD
-
ANC
Nonstop6h 51m
United Airlines
Deal found 1/14$387
This Delta deal was found by Cheapflights users on 1/14. 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.
Fri 3/139:15 pm
ANC
-
MDW
1 stop13h 10m
Delta
Fri 3/209:30 am
MDW
-
ANC
1 stop12h 21m
Delta
Deal found 1/14$388

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 January 14, 2026.
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

Thu 4/23

6:00 am-7:52 pm

1 stop10h 52m

Chicago O'Hare Intl

Mon 4/27

6:00 am-1:08 pm

1 stop10h 08m

$359

AnchorageChicago

ANC - ORD

ANCORD

Anchorage

Fri 4/24

2:26 am-2:56 pm

1 stop9h 30m

Chicago O'Hare Intl

Tue 4/28

8:00 am-3:17 pm

1 stop10h 17m

$359

AnchorageChicago

ANC - ORD

ANCORD

Anchorage

Sat 4/25

2:26 am-2:56 pm

1 stop9h 30m

Chicago O'Hare Intl

Fri 5/1

6:00 am-1:08 pm

1 stop10h 08m

$359

AnchorageChicago

ANC - ORD

ANCORD

Anchorage

Wed 4/22

8:00 am-7:52 pm

1 stop8h 52m

Chicago O'Hare Intl

Fri 5/1

6:00 am-2:02 pm

1 stop11h 02m

$359

AnchorageChicago

ANC - ORD

ANCORD

Anchorage

Wed 2/11

12:29 am-2:11 pm

1 stop10h 42m

Chicago O'Hare Intl

Tue 2/17

2:07 pm-12:30 am

1 stop13h 23m

$359

AnchorageChicago

ANC - ORD

ANCORD

Anchorage

Tue 4/21

10:48 am-11:59 pm

1 stop10h 11m

Chicago O'Hare Intl

Tue 4/28

2:19 pm-8:44 pm

1 stop9h 25m

$359

AnchorageChicago

ANC - ORD

ANCORD

Anchorage

Tue 4/21

6:00 am-6:26 pm

1 stop9h 26m

Chicago O'Hare Intl

Fri 5/1

6:00 am-2:02 pm

1 stop11h 02m

$359

AnchorageChicago

ANC - ORD

ANCORD

Anchorage

Thu 4/23

5:25 pm-6:40 am

1 stop10h 15m

Chicago O'Hare Intl

Fri 5/1

6:00 am-1:08 pm

1 stop10h 08m

$359

AnchorageChicago

ANC - ORD

ANCORD

Anchorage

Thu 4/23

8:00 am-7:52 pm

1 stop8h 52m

Chicago O'Hare Intl

Wed 4/29

3:37 pm-12:42 am

1 stop12h 05m

$359

AnchorageChicago

ANC - ORD

ANCORD

Anchorage

Fri 4/24

8:00 am-7:52 pm

1 stop8h 52m

Chicago O'Hare Intl

Tue 4/28

3:37 pm-11:44 pm

1 stop11h 07m

$359

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/12

Showing 1-10 of 60 results
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6

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 January is currently the most expensive (average of $654). 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.

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

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 January 14, 2026.
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
11,713 reviews

Entertainment

7.0

Food

7.1

Overall

8.0

Boarding

8.1

Comfort

7.8

Crew

8.5

Reviews

1 / 20
4.0
Okay

Anonymous,Dec 2025

SEA - MSY

I really got a lesson in upgrades. I let my seat get chosen . Both times a middle seat...on purpose ...even when we were not full. That's petty I sat behind the first class . They got more than 1 drink ...and a snack . .and the staff actually talked to them...behind a see thru shawl/sheet in the aisle....... You could see over the seats just fine and you could hear the voices just fine. But the sheet let You KNOW. Your not welcome here. For a moment I regretted not spending 300 dollars per seat so I could see a smile and eat a sandwhich and enjoy my seat . The married couple drank champain and laughed and flirted with each other. It looked so happy and care free MONEY really does buy happiness ..the hateful glares and sighs from my seat mates brought me back to reality I wasn't rich and I still had 2 hours left in this middle seat.
Alaska Airlines
8.0
Very good
11,713 reviews
Alaska Airlines
8.0
Very good
11,713 reviews

Entertainment

7.0

Food

7.1

Overall

8.0

Boarding

8.1

Comfort

7.8

Crew

8.5

Reviews

1 / 20
4.0
Okay

Anonymous,Dec 2025

SEA - MSY

I really got a lesson in upgrades. I let my seat get chosen . Both times a middle seat...on purpose ...even when we were not full. That's petty I sat behind the first class . They got more than 1 drink ...and a snack . .and the staff actually talked to them...behind a see thru shawl/sheet in the aisle....... You could see over the seats just fine and you could hear the voices just fine. But the sheet let You KNOW. Your not welcome here. For a moment I regretted not spending 300 dollars per seat so I could see a smile and eat a sandwhich and enjoy my seat . The married couple drank champain and laughed and flirted with each other. It looked so happy and care free MONEY really does buy happiness ..the hateful glares and sighs from my seat mates brought me back to reality I wasn't rich and I still had 2 hours left in this middle seat.
Delta
7.9
Good
8,048 reviews
Alaska Airlines
8.0
Very good
11,713 reviews

Entertainment

7.0

Food

7.1

Overall

8.0

Boarding

8.1

Comfort

7.8

Crew

8.5

Reviews

1 / 20
4.0
Okay

Anonymous,Dec 2025

SEA - MSY

I really got a lesson in upgrades. I let my seat get chosen . Both times a middle seat...on purpose ...even when we were not full. That's petty I sat behind the first class . They got more than 1 drink ...and a snack . .and the staff actually talked to them...behind a see thru shawl/sheet in the aisle....... You could see over the seats just fine and you could hear the voices just fine. But the sheet let You KNOW. Your not welcome here. For a moment I regretted not spending 300 dollars per seat so I could see a smile and eat a sandwhich and enjoy my seat . The married couple drank champain and laughed and flirted with each other. It looked so happy and care free MONEY really does buy happiness ..the hateful glares and sighs from my seat mates brought me back to reality I wasn't rich and I still had 2 hours left in this middle seat.
Hawaiian Airlines
7.8
Good
2,827 reviews
Alaska Airlines
8.0
Very good
11,713 reviews

Entertainment

7.0

Food

7.1

Overall

8.0

Boarding

8.1

Comfort

7.8

Crew

8.5

Reviews

1 / 20
4.0
Okay

Anonymous,Dec 2025

SEA - MSY

I really got a lesson in upgrades. I let my seat get chosen . Both times a middle seat...on purpose ...even when we were not full. That's petty I sat behind the first class . They got more than 1 drink ...and a snack . .and the staff actually talked to them...behind a see thru shawl/sheet in the aisle....... You could see over the seats just fine and you could hear the voices just fine. But the sheet let You KNOW. Your not welcome here. For a moment I regretted not spending 300 dollars per seat so I could see a smile and eat a sandwhich and enjoy my seat . The married couple drank champain and laughed and flirted with each other. It looked so happy and care free MONEY really does buy happiness ..the hateful glares and sighs from my seat mates brought me back to reality I wasn't rich and I still had 2 hours left in this middle seat.
United Airlines
7.4
Good
9,163 reviews
Alaska Airlines
8.0
Very good
11,713 reviews

Entertainment

7.0

Food

7.1

Overall

8.0

Boarding

8.1

Comfort

7.8

Crew

8.5

Reviews

1 / 20
4.0
Okay

Anonymous,Dec 2025

SEA - MSY

I really got a lesson in upgrades. I let my seat get chosen . Both times a middle seat...on purpose ...even when we were not full. That's petty I sat behind the first class . They got more than 1 drink ...and a snack . .and the staff actually talked to them...behind a see thru shawl/sheet in the aisle....... You could see over the seats just fine and you could hear the voices just fine. But the sheet let You KNOW. Your not welcome here. For a moment I regretted not spending 300 dollars per seat so I could see a smile and eat a sandwhich and enjoy my seat . The married couple drank champain and laughed and flirted with each other. It looked so happy and care free MONEY really does buy happiness ..the hateful glares and sighs from my seat mates brought me back to reality I wasn't rich and I still had 2 hours left in this middle seat.
American Airlines
7.2
Good
11,129 reviews
Alaska Airlines
8.0
Very good
11,713 reviews

Entertainment

7.0

Food

7.1

Overall

8.0

Boarding

8.1

Comfort

7.8

Crew

8.5

Reviews

1 / 20
4.0
Okay

Anonymous,Dec 2025

SEA - MSY

I really got a lesson in upgrades. I let my seat get chosen . Both times a middle seat...on purpose ...even when we were not full. That's petty I sat behind the first class . They got more than 1 drink ...and a snack . .and the staff actually talked to them...behind a see thru shawl/sheet in the aisle....... You could see over the seats just fine and you could hear the voices just fine. But the sheet let You KNOW. Your not welcome here. For a moment I regretted not spending 300 dollars per seat so I could see a smile and eat a sandwhich and enjoy my seat . The married couple drank champain and laughed and flirted with each other. It looked so happy and care free MONEY really does buy happiness ..the hateful glares and sighs from my seat mates brought me back to reality I wasn't rich and I still had 2 hours left in this middle seat.

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 8h 53m. Alaska Airlines provides one of the quickest options available for as low as $379. 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 Hawaiian Airlines ($156), United Airlines ($158), and American Airlines ($158).

  • 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 January is currently the most expensive (average of $654). 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

See prices for flight routes from nearby airports that may be better suited for you.
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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 January 14, 2026.
AirlineCheapestAverageFlexibilityOn-time
Hawaiian AirlinesCheapest$187Average$461FlexibilityNo cancel feeOn-time85%
DeltaCheapest$259Average$408FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$314Average$496FlexibilityNo cancel feeOn-time69%
Alaska AirlinesCheapest$318Average$608FlexibilityNo cancel feeOn-time75%
American AirlinesCheapest$338Average$513FlexibilityNo cancel feeOn-time71%

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