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$205+ 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 11/9. Fares are subject to change and may not be available on all flights or dates of travel.
KOA — CHI
Oct 17 — Oct 241
Fri 10/17
Fri 10/24
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 September 17, 2025.

Round-trip from

$477
(United Airlines)

One-way from

$205
(Delta)
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 September 17, 2025.

This United Airlines deal was found by Cheapflights users on 9/15. 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 10/158:00 pmKOA - ORD
1 stop12h 12mUnited Airlines
Fri 10/176:15 amORD - KOA
1 stop10h 41mUnited Airlines
Deal found 9/15$477
This Alaska Airlines deal was found by Cheapflights users on 9/16. 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 10/1710:27 amKOA - ORD
1 stop14h 57mAlaska Airlines
Sun 10/196:00 amORD - KOA
2 stops16h 47mAlaska Airlines
Deal found 9/16$529
This United Airlines deal was found by Cheapflights users on 9/16. 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 10/91:05 pmKOA - ORD
1 stop12h 05mUnited Airlines
Sun 10/127:10 amORD - KOA
1 stop13h 15mUnited Airlines
Deal found 9/16$533
This Alaska Airlines deal was found by Cheapflights users on 9/15. 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 10/158:00 amKOA - ORD
1 stop10h 59mAlaska Airlines
Fri 10/177:00 amORD - KOA
2 stops19h 40mAlaska Airlines
Deal found 9/15$613
This Southwest deal was found by Cheapflights users on 9/15. 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.
Mon 9/228:30 pmKOA - MDW
1 stop11h 45mSouthwest
Mon 9/295:15 amMDW - KOA
1 stop11h 55mSouthwest
Deal found 9/15$643
This Delta deal was found by Cheapflights users on 9/15. 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 9/189:30 pmKOA - ORD
1 stop14h 45mDelta
Tue 9/307:10 amORD - KOA
1 stop15h 19mDelta
Deal found 9/15$643
This Delta deal was found by Cheapflights users on 9/16. 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 10/19:30 pmKOA - ORD
1 stop14h 45mDelta
Sun 10/57:10 amORD - KOA
1 stop15h 19mDelta
Deal found 9/16$672
This Alaska Airlines deal was found by Cheapflights users on 9/15. 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 9/305:26 pmITO - ORD
2 stops15h 58mAlaska Airlines
Sat 10/410:05 amORD - ITO
2 stops17h 14mAlaska Airlines
Deal found 9/15$744
This Southwest deal was found by Cheapflights users on 9/15. 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.
Wed 10/158:30 pmKOA - MDW
2 stops12h 55mSouthwest
Fri 10/175:40 amMDW - KOA
1 stop12h 20mSouthwest
Deal found 9/15$798
This Delta deal was found by Cheapflights users on 9/16. 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 10/19:30 pmKOA - MDW
2 stops15h 05mDelta
Sun 10/56:00 amMDW - KOA
2 stops18h 12mDelta
Deal found 9/16$800
This Southwest deal was found by Cheapflights users on 9/17. 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.
Sun 9/286:00 amITO - ORD
2 stops12h 40mSouthwest
Wed 10/16:15 amORD - ITO
2 stops16h 55mSouthwest
Deal found 9/17$849
This Delta deal was found by Cheapflights users on 9/15. 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 9/181:42 pmKOA - MDW
2 stops14h 07mDelta
Tue 9/309:35 amMDW - KOA
2 stops13h 00mDelta
Deal found 9/15$854

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 September 17, 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

Wed 10/15

8:00 pm-1:12 pm

1 stop12h 12m

Chicago O'Hare Intl

Fri 10/17

6:15 am-11:56 am

1 stop10h 41m

$477

HiloChicago

ITO - ORD

ITOORD

Hilo Intl

Tue 2/24

6:47 pm-11:10 pm

2 stops24h 23m

Chicago O'Hare Intl

Fri 2/27

2:59 pm-5:00 pm

2 stops30h 01m

$494

Kailua-KonaChicago

KOA - ORD

KOAORD

Kona Intl

Fri 10/17

10:27 am-6:24 am

1 stop14h 57m

Chicago O'Hare Intl

Sun 10/19

6:00 am-5:47 pm

2 stops16h 47m

$529

Kailua-KonaChicago

KOA - ORD

KOAORD

Kona Intl

Thu 10/9

1:05 pm-6:10 am

1 stop12h 05m

Chicago O'Hare Intl

Sun 10/12

7:10 am-3:25 pm

1 stop13h 15m

$533

Kailua-KonaChicago

KOA - MDW

KOAMDW

Kona Intl

Mon 9/22

8:30 pm-1:15 pm

1 stop11h 45m

Chicago Midway

Mon 9/29

5:15 am-12:10 pm

1 stop11h 55m

$643

Kailua-KonaChicago

KOA - ORD

KOAORD

Kona Intl

Thu 10/2

8:00 am-12:03 am

1 stop11h 03m

Chicago O'Hare Intl

Mon 10/6

6:00 am-1:54 pm

1 stop12h 54m

$643

Kailua-KonaChicago

KOA - ORD

KOAORD

Kona Intl

Thu 10/2

9:30 pm-6:30 pm

2 stops16h 00m

Chicago O'Hare Intl

Mon 10/6

7:37 am-5:30 pm

1 stop14h 53m

$648

Kailua-KonaChicago

KOA - ORD

KOAORD

Kona Intl

Wed 10/1

9:30 pm-5:15 pm

1 stop14h 45m

Chicago O'Hare Intl

Sun 10/5

7:10 am-5:29 pm

1 stop15h 19m

$672

HiloChicago

ITO - ORD

ITOORD

Hilo Intl

Tue 9/30

5:26 pm-2:24 pm

2 stops15h 58m

Chicago O'Hare Intl

Sat 10/4

10:05 am-10:19 pm

2 stops17h 14m

$744

Kailua-KonaChicago

KOA - MDW

KOAMDW

Kona Intl

Wed 10/15

8:30 pm-2:25 pm

2 stops12h 55m

Chicago Midway

Fri 10/17

5:40 am-1:00 pm

1 stop12h 20m

$798

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/16

Showing 1-10 of 41 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 September 17, 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.

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.

  • How long is the flight from The Big Island to Chicago?

    Departing from The Big Island to Chicago will take you 11h 45m. The distance from The Big Island to Chicago is about 4213 mi. This flight may include one or multiple stops.

  • What are the cheapest airlines to fly from The Big Island to Chicago one-way?

    The cheapest airline one-way is Delta, with whom users have recently found tickets for as low as $205. However, be on the lookout for offers from Alaska Airlines and Southwest, 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 Kona Intl - Chicago O'Hare Intl, Kona Intl - Chicago Midway or Hilo 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
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 September 17, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$429Average$783FlexibilityNo cancel feeOn-time69%
Alaska AirlinesCheapest$458Average$831FlexibilityNo cancel feeOn-time75%
American AirlinesCheapest$545Average$726FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$693Average$768FlexibilityNo cancel feeOn-time63%

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