Illinois

$182+ 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 5/28. Fares are subject to change and may not be available on all flights or dates of travel.
ANC — ORD
May 31 — Jun 71
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Cheap 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 May 1, 2026.

This Vliegwinkel deal was found by Cheapflights users on 4/27. 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 Vliegwinkel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/1811:08 pm
ANC
-
ORD
Nonstop6h 17m
Alaska Airlines
Sun 5/246:00 am
ORD
-
ANC
1 stop9h 04m
Alaska Airlines
Deal found 4/27$360
This American Airlines deal was found by Cheapflights users on 4/27. 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.
Thu 6/49:50 pm
ANC
-
ORD
Nonstop6h 33m
American Airlines
Mon 6/85:02 pm
ORD
-
ANC
Nonstop6h 39m
American Airlines
Deal found 4/27$367
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.
Thu 7/166:00 am
ANC
-
STL
2 stops14h 53m
Delta
Sat 7/255:36 pm
STL
-
ANC
1 stop10h 23m
Delta
Deal found 4/30$370
This American Airlines deal was found by Cheapflights users on 4/27. 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.
Fri 6/57:00 am
ANC
-
ORD
1 stop10h 11m
American Airlines
Mon 6/85:02 pm
ORD
-
ANC
Nonstop6h 39m
American Airlines
Deal found 4/27$377
This Alaska Airlines deal was found by Cheapflights users on 4/25. 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 5/2711:08 pm
ANC
-
ORD
Nonstop6h 17m
Alaska Airlines
Wed 6/108:05 pm
ORD
-
ANC
1 stop15h 35m
Alaska Airlines
Deal found 4/25$383
This Delta deal was found by Cheapflights users on 4/25. 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 5/279:30 pm
ANC
-
ORD
1 stop12h 31m
Delta
Mon 6/87:01 am
ORD
-
ANC
1 stop17h 15m
Delta
Deal found 4/25$387
This Delta deal was found by Cheapflights users on 4/27. 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 5/186:00 am
ANC
-
MDW
1 stop8h 56m
Delta
Sun 5/246:23 am
MDW
-
ANC
1 stop15h 15m
Delta
Deal found 4/27$387
This United Airlines deal was found by Cheapflights users on 4/26. 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.
Wed 8/2611:59 pm
ANC
-
ORD
Nonstop6h 10m
United Airlines
Sun 8/306:00 am
ORD
-
ANC
1 stop11h 05m
United Airlines
Deal found 4/26$389
This Delta deal was found by Cheapflights users on 4/27. 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 5/291:55 am
ANC
-
ORD
1 stop12h 18m
Delta
Tue 6/97:45 am
ORD
-
ANC
2 stops15h 22m
Delta
Deal found 4/27$392
This Delta deal was found by Cheapflights users on 4/26. 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 5/246:00 am
ANC
-
MDW
2 stops12h 09m
Delta
Sun 5/319:22 am
MDW
-
ANC
1 stop13h 54m
Delta
Deal found 4/26$392
This Alaska Airlines deal was found by Cheapflights users on 4/27. 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 5/3011:08 pm
ANC
-
ORD
Nonstop6h 17m
Alaska Airlines
Thu 6/1112:59 am
ORD
-
ANC
Nonstop6h 42m
Alaska Airlines
Deal found 4/27$393
This Delta deal was found by Cheapflights users on 4/27. 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 5/318:05 pm
ANC
-
ORD
1 stop14h 42m
Delta
Wed 6/107:45 am
ORD
-
ANC
2 stops15h 22m
Delta
Deal found 4/27$398

Find flight deals from Alaska to Illinois

Keep the following information in mind while searching for Alaska to Illinois flight deals. Data was last updated May 1, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$360
(Vliegwinkel)

One-way from

$182
(Southwest)

Popular in

July

Cheapest in

October

Average price

$521

Good round-trip deal

$574 or less

Good one-way deal

$291 or less
Provider with most accurate pricing for Anchorage-Chicago (CHI) flight deals.
Provider most trusted by Cheapflights users for Anchorage-Chicago (CHI) flights.
From Alaska to Illinois
One-way flight from Alaska to Illinois
Highest demand for flights based on searches. 9% potential increase in price ($48 potential increase over avg. RT price).
Cheapest flight prices on average. 2% potential price decrease ($12 potential savings vs. average RT price).
Average for round-trip flights in May 2026
Price to beat on a round-trip flight from Alaska to Illinois.
Price to beat on a one-way flight from Alaska to Illinois.

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 May 1, 2026.
Use the filters below to find and compare flights from Alaska to Illinois that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

AnchorageChicago

ANC - ORD

ANCORD

Anchorage

Tue 6/2

11:08 pm-8:25 am

Nonstop6h 17m

Chicago O'Hare Intl

Wed 6/10

8:05 pm-8:40 am

1 stop15h 35m

$383

AnchorageChicago

ANC - ORD

ANCORD

Anchorage

Sat 5/30

11:08 pm-8:25 am

Nonstop6h 17m

Chicago O'Hare Intl

Fri 6/12

8:05 pm-8:40 am

1 stop15h 35m

$383

AnchorageChicago

ANC - ORD

ANCORD

Anchorage

Tue 6/2

6:00 am-7:20 pm

1 stop10h 20m

Chicago O'Hare Intl

Tue 6/9

6:55 am-4:15 pm

1 stop12h 20m

$387

AnchorageChicago

ANC - ORD

ANCORD

Anchorage

Wed 9/2

1:30 am-5:22 pm

1 stop12h 52m

Chicago O'Hare Intl

Mon 9/7

3:50 pm-8:59 pm

1 stop8h 09m

$399

AnchorageChicago

ANC - ORD

ANCORD

Anchorage

Thu 7/23

6:00 am-11:38 pm

1 stop14h 38m

Chicago O'Hare Intl

Sun 7/26

8:52 am-9:20 pm

1 stop15h 28m

$399

AnchorageChicago

ANC - MDW

ANCMDW

Anchorage

Wed 8/26

10:00 pm-12:30 pm

1 stop11h 30m

Chicago Midway

Sun 8/30

1:00 pm-8:58 pm

1 stop10h 58m

$399

AnchorageSt. Louis

ANC - STL

ANCSTL

Anchorage

Sat 5/23

7:24 pm-3:16 pm

1 stop16h 52m

Lambert-St Louis

Wed 5/27

5:33 pm-10:30 am

1 stop19h 57m

$402

AnchorageChicago

ANC - ORD

ANCORD

Anchorage

Fri 9/11

6:05 am-11:41 pm

2 stops14h 36m

Chicago O'Hare Intl

Sun 9/13

6:01 am-6:38 pm

2 stops15h 37m

$409
Quickest round-trip

AnchorageChicago

ANC - ORD

ANCORD

Anchorage

Thu 5/28

9:30 pm-10:29 am

1 stop9h 59m

Chicago O'Hare Intl

Tue 6/9

3:55 pm-8:52 pm

1 stop7h 57m

$419

AnchorageChicago

ANC - ORD

ANCORD

Anchorage

Sat 8/29

6:05 am-11:59 pm

1 stop14h 54m

Chicago O'Hare Intl

Tue 9/1

8:00 am-11:44 am

Nonstop6h 44m

$419

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/26

Showing 1-10 of 60 resultsSorted by cheapest first
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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

How far ahead should I book a flight from Alaska to Illinois?

Booking 71 days in advance of your planned departure date is, on average, the best time to get cheap flights from Alaska to Illinois. The general trend is that the closer you book to the departure date, the more expensive your flight will be.

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

Currently, August is the cheapest month in which you can book a flight from Alaska to Illinois (average of $158). Flying from Alaska to Illinois in January is currently the most expensive (average of $408). 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 May 1, 2026.

When flying from Alaska to Illinois, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

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 May 1, 2026.

The most flights from USAK to USIL are scheduled on a Monday (4 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (4 on average).

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 May 1, 2026.
Read reviews from past customers who have flown Alaska Airlines,Delta, andHawaiian 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.

Boarding

8.1

Overall

7.9

Food

7.1

Entertainment

7.0

Crew

8.5

Comfort

7.8

Reviews

1 / 20
8.0
Excellent

Eugene,Mar 2026

MFR - SEA

Alaska Airlines is is always good. There where few choices of what to drink, and no food. No blankets, no pillows, and you h ats ok. I just had open heart surgery And i could have used something. But the flight and the crew where exelent. So all is well

Boarding

8.1

Overall

7.9

Food

7.1

Entertainment

7.0

Crew

8.5

Comfort

7.8

Reviews

1 / 20
8.0
Excellent

Eugene,Mar 2026

MFR - SEA

Alaska Airlines is is always good. There where few choices of what to drink, and no food. No blankets, no pillows, and you h ats ok. I just had open heart surgery And i could have used something. But the flight and the crew where exelent. So all is well

Boarding

8.1

Overall

7.9

Food

7.1

Entertainment

7.0

Crew

8.5

Comfort

7.8

Reviews

1 / 20
8.0
Excellent

Eugene,Mar 2026

MFR - SEA

Alaska Airlines is is always good. There where few choices of what to drink, and no food. No blankets, no pillows, and you h ats ok. I just had open heart surgery And i could have used something. But the flight and the crew where exelent. So all is well

Boarding

8.1

Overall

7.9

Food

7.1

Entertainment

7.0

Crew

8.5

Comfort

7.8

Reviews

1 / 20
8.0
Excellent

Eugene,Mar 2026

MFR - SEA

Alaska Airlines is is always good. There where few choices of what to drink, and no food. No blankets, no pillows, and you h ats ok. I just had open heart surgery And i could have used something. But the flight and the crew where exelent. So all is well

Boarding

8.1

Overall

7.9

Food

7.1

Entertainment

7.0

Crew

8.5

Comfort

7.8

Reviews

1 / 20
8.0
Excellent

Eugene,Mar 2026

MFR - SEA

Alaska Airlines is is always good. There where few choices of what to drink, and no food. No blankets, no pillows, and you h ats ok. I just had open heart surgery And i could have used something. But the flight and the crew where exelent. So all is well

Boarding

8.1

Overall

7.9

Food

7.1

Entertainment

7.0

Crew

8.5

Comfort

7.8

Reviews

1 / 20
8.0
Excellent

Eugene,Mar 2026

MFR - SEA

Alaska Airlines is is always good. There where few choices of what to drink, and no food. No blankets, no pillows, and you h ats ok. I just had open heart surgery And i could have used something. But the flight and the crew where exelent. So all is well

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 6h 17m. Alaska Airlines provides one of the quickest options available for as low as $383. Airlines will cover a distance of 2837 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), Alaska Airlines ($158), and United 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, August is the cheapest month in which you can book a flight from Alaska to Illinois (average of $158). Flying from Alaska to Illinois in January is currently the most expensive (average of $408). 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

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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.

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 May 1, 2026.
AirlineCheapestAverageFlexibilityOn-time
Hawaiian AirlinesCheapest$158Average$461FlexibilityNo cancel feeOn-time85%
United AirlinesCheapest$314Average$546FlexibilityNo cancel feeOn-time69%
Alaska AirlinesCheapest$314Average$482FlexibilityNo cancel feeOn-time75%
American AirlinesCheapest$331Average$497FlexibilityNo cancel feeOn-time71%
DeltaCheapest$337Average$440FlexibilityNo cancel feeOn-timeN/A

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