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$210+ Cheap flights from The Big Island 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 12/5. Fares are subject to change and may not be available on all flights or dates of travel.
KOA — CHI
Aug 7 — Aug 141
Thu 8/7
Thu 8/14
1 adult, Economy
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Cheap flight deals from The Big Island to Chicago

Keep the following information in mind while searching for The Big Island to Chicago flight deals. Data was last updated August 2, 2025.

Round-trip from

$408
(Alaska Airlines)

One-way from

$210
(Alaska Airlines)
From The Big Island to Chicago (CHI)
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One-way flight from The Big Island to Chicago (CHI)
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Find flight deals from The Big Island to Chicago

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

This American Airlines deal was found by Cheapflights users on 7/31. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/89:55 pmKOA - ORD
1 stop13h 03mAmerican Airlines
Sun 9/146:00 amORD - KOA
1 stop12h 42mAmerican Airlines
Deal found 7/31$409
This Delta deal was found by Cheapflights users on 7/31. 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.
Sun 9/219:30 pmKOA - ORD
1 stop10h 50mDelta
Thu 9/257:10 amORD - KOA
1 stop15h 19mDelta
Deal found 7/31$423
This Alaska Airlines deal was found by Cheapflights users on 7/31. 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.
Mon 9/86:00 pmKOA - ORD
2 stops14h 11mAlaska Airlines
Sun 9/146:20 amORD - KOA
2 stops14h 31mAlaska Airlines
Deal found 7/31$429
This Southwest deal was found by Cheapflights users on 7/31. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/199:15 amKOA - MDW
2 stops14h 55mSouthwest
Tue 8/266:10 amMDW - KOA
1 stop11h 00mSouthwest
Deal found 7/31$566
This Alaska Airlines deal was found by Cheapflights users on 7/31. 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.
Wed 11/196:00 amITO - ORD
2 stops14h 24mAlaska Airlines
Tue 12/26:50 pmORD - ITO
2 stops24h 28mAlaska Airlines
Deal found 7/31$644
This Delta deal was found by Cheapflights users on 8/1. 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.
Mon 9/88:41 pmKOA - MDW
2 stops16h 56mDelta
Sun 9/146:00 amMDW - KOA
2 stops17h 41mDelta
Deal found 8/1$765
This United Airlines deal was found by Cheapflights users on 7/31. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/197:43 pmITO - ORD
1 stop30h 25mUnited Airlines
Tue 12/21:00 pmORD - ITO
2 stops33h 18mUnited Airlines
Deal found 7/31$767
This United Airlines deal was found by Cheapflights users on 7/31. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/161:15 pmKOA - ORD
1 stop12h 05mUnited Airlines
Wed 8/206:00 amORD - KOA
2 stops18h 34mUnited Airlines
Deal found 7/31$818
This American Airlines deal was found by Cheapflights users on 7/31. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/194:34 pmITO - ORD
1 stop10h 36mAmerican Airlines
Tue 12/210:00 amORD - ITO
1 stop12h 18mAmerican Airlines
Deal found 7/31$1,310

Cheapflights Fare Finder

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

Fly from

The Big Island

Fly to

Chicago

Route

Depart

Return

Price

Kailua-KonaChicago

KOA - ORD

KOAORD

Kona Intl

Thu 1/15

12:00 pm-1:59 pm

1 stop21h 59m

Chicago O'Hare Intl

Wed 1/21

2:59 pm-2:46 pm

1 stop27h 47m

$408

Kailua-KonaChicago

KOA - ORD

KOAORD

Kona Intl

Mon 9/8

9:55 pm-3:58 pm

1 stop13h 03m

Chicago O'Hare Intl

Sun 9/14

6:00 am-1:42 pm

1 stop12h 42m

$409

Kailua-KonaChicago

KOA - ORD

KOAORD

Kona Intl

Sun 9/21

9:30 pm-1:20 pm

1 stop10h 50m

Chicago O'Hare Intl

Thu 9/25

7:10 am-5:29 pm

1 stop15h 19m

$423

Kailua-KonaChicago

KOA - MDW

KOAMDW

Kona Intl

Tue 8/19

9:15 am-5:10 am

2 stops14h 55m

Chicago Midway

Tue 8/26

6:10 am-12:10 pm

1 stop11h 00m

$566

HiloChicago

ITO - ORD

ITOORD

Hilo Intl

Wed 11/19

6:00 am-12:24 am

2 stops14h 24m

Chicago O'Hare Intl

Tue 12/2

6:50 pm-3:18 pm

2 stops24h 28m

$644

Kailua-KonaChicago

KOA - MDW

KOAMDW

Kona Intl

Mon 9/8

8:41 pm-6:37 pm

2 stops16h 56m

Chicago Midway

Sun 9/14

6:00 am-6:41 pm

2 stops17h 41m

$765

HiloChicago

ITO - ORD

ITOORD

Hilo Intl

Wed 11/19

7:43 pm-6:08 am

1 stop30h 25m

Chicago O'Hare Intl

Tue 12/2

1:00 pm-6:18 pm

2 stops33h 18m

$767

Kailua-KonaChicago

KOA - ORD

KOAORD

Kona Intl

Sat 8/16

1:15 pm-6:20 am

1 stop12h 05m

Chicago O'Hare Intl

Wed 8/20

6:00 am-7:34 pm

2 stops18h 34m

$818

HiloChicago

ITO - ORD

ITOORD

Hilo Intl

Wed 11/19

4:34 pm-7:10 am

1 stop10h 36m

Chicago O'Hare Intl

Tue 12/2

10:00 am-6:18 pm

1 stop12h 18m

$1,310

Kailua-KonaChicago

KOA - ORD

KOAORD

Kona Intl

Fri 12/5

12:00 pm-1:59 pm

1 stop21h 59m

$210

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/31

Showing 1-10 of 18 results
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Best time to book a flight from The Big Island to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from The Big Island 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 The Big Island to Chicago

What is the cheapest month to book a flight from The Big Island to Chicago?

Currently, August is the cheapest month in which you can book a flight from The Big Island to Chicago (average of $245). Flying from The Big Island 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 FUI to CHI?

Find hourly flight availability from The Big Island 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 August 2, 2025.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from The Big Island to Chicago as you normally would.

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 August 2, 2025.
Read through reviews of airlines operating flights from The Big Island to Chicago, such as Alaska Airlines, Southwest, and Delta. 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
10,000 reviews

Food

7.1

Overall

8.0

Crew

8.5

Boarding

8.1

Entertainment

7.1

Comfort

7.8

Reviews

1 / 20
10.0
Excellent

Jonathan,Jul 2025

SEA - BOS

Fantastic Check-in with easy baggage drop. While it took a while to find out which was the gate, the boarding was a dream, the stewards were simply incredible and the flight fantastic.
Alaska Airlines
8.0
Very good
10,000 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Food

7.1

Overall

8.0

Crew

8.5

Boarding

8.1

Entertainment

7.1

Comfort

7.8

Reviews

1 / 20
10.0
Excellent

Jonathan,Jul 2025

SEA - BOS

Fantastic Check-in with easy baggage drop. While it took a while to find out which was the gate, the boarding was a dream, the stewards were simply incredible and the flight fantastic.
Southwest
8.0
Very good
4,246 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Food

7.1

Overall

8.0

Crew

8.5

Boarding

8.1

Entertainment

7.1

Comfort

7.8

Reviews

1 / 20
10.0
Excellent

Jonathan,Jul 2025

SEA - BOS

Fantastic Check-in with easy baggage drop. While it took a while to find out which was the gate, the boarding was a dream, the stewards were simply incredible and the flight fantastic.
Delta
8.0
Very good
7,983 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Food

7.1

Overall

8.0

Crew

8.5

Boarding

8.1

Entertainment

7.1

Comfort

7.8

Reviews

1 / 20
10.0
Excellent

Jonathan,Jul 2025

SEA - BOS

Fantastic Check-in with easy baggage drop. While it took a while to find out which was the gate, the boarding was a dream, the stewards were simply incredible and the flight fantastic.
United Airlines
7.4
Good
8,904 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Food

7.1

Overall

8.0

Crew

8.5

Boarding

8.1

Entertainment

7.1

Comfort

7.8

Reviews

1 / 20
10.0
Excellent

Jonathan,Jul 2025

SEA - BOS

Fantastic Check-in with easy baggage drop. While it took a while to find out which was the gate, the boarding was a dream, the stewards were simply incredible and the flight fantastic.
American Airlines
7.2
Good
10,000 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Food

7.1

Overall

8.0

Crew

8.5

Boarding

8.1

Entertainment

7.1

Comfort

7.8

Reviews

1 / 20
10.0
Excellent

Jonathan,Jul 2025

SEA - BOS

Fantastic Check-in with easy baggage drop. While it took a while to find out which was the gate, the boarding was a dream, the stewards were simply incredible and the flight fantastic.

Related info for your journey

Find useful and relevant information for your journey from The Big Island 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 The Big Island to Chicago one-way?

    The cheapest airline one-way is Alaska Airlines, with whom users have recently found tickets for as low as $210. However, be on the lookout for offers from American Airlines and Delta, as they are both options that can get you from The Big Island to Chicago for a low price.

  • What are the most popular routes from The Big Island to Chicago?

    When deciding which route to take from The Big Island to Chicago consider Hilo Intl - Chicago O'Hare Intl, Kona Intl - Chicago Midway or Kona Intl - Chicago O'Hare Intl as they are the most popular.

  • Can I find deals for flights from The Big Island to Chicago that include hotel bookings?

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

  • How can I find direct flights from The Big Island to Chicago?

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

  • Can I find deals for business class flights from The Big Island to Chicago?

    Yes. Cheapflights offers flight deals from The Big Island 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 The Big Island to Chicago?

    Currently, August is the cheapest month in which you can book a flight from The Big Island to Chicago (average of $245). Flying from The Big Island 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 Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
Lansing
Hammond
Benton Harbor
Porter
Valparaiso
Chesterton

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Top 4 airlines flying from The Big Island to Chicago

Discover the top 4 airlines that operate flights from The Big Island 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 August 2, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$419Average$623FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$429Average$843FlexibilityNo cancel feeOn-time69%
Alaska AirlinesCheapest$507Average$836FlexibilityNo cancel feeOn-time75%
SouthwestCheapest$693Average$768FlexibilityNo cancel feeOn-time63%

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