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$211+ 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 2/6. Fares are subject to change and may not be available on all flights or dates of travel.
KOA — CHI
Jan 17 — Jan 241
Sat 1/17
Sat 1/24
1 adult, Economy
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Cheap 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 December 18, 2025.

This American Airlines deal was found by Cheapflights users on 12/16. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/316:30 pmKOA - ORD
1 stop11h 14mAmerican Airlines
Sun 1/48:15 amORD - KOA
1 stop12h 23mAmerican Airlines
Deal found 12/16$712
This Delta deal was found by Cheapflights users on 12/16. 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 12/3110:55 pmKOA - ORD
2 stops18h 41mDelta
Sun 1/47:25 amORD - KOA
1 stop12h 23mDelta
Deal found 12/16$717
This American Airlines deal was found by Cheapflights users on 12/16. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/266:30 pmKOA - ORD
1 stop10h 10mAmerican Airlines
Sun 12/286:00 amORD - KOA
1 stop12h 54mAmerican Airlines
Deal found 12/16$948
This American Airlines deal was found by Cheapflights users on 12/16. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/2410:09 pmKOA - ORD
1 stop15h 43mAmerican Airlines
Mon 12/295:21 amORD - KOA
1 stop13h 55mAmerican Airlines
Deal found 12/16$969
This United Airlines deal was found by Cheapflights users on 12/16. 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.
Wed 12/2411:20 pmKOA - ORD
1 stop25h 17mUnited Airlines
Mon 12/299:15 pmORD - KOA
2 stops19h 36mUnited Airlines
Deal found 12/16$977
This Southwest deal was found by Cheapflights users on 12/16. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/243:40 pmKOA - ORD
2 stops17h 50mSouthwest
Mon 12/297:15 amORD - KOA
2 stops14h 55mSouthwest
Deal found 12/16$984
This Southwest deal was found by Cheapflights users on 12/16. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/249:15 pmKOA - MDW
1 stop12h 25mSouthwest
Mon 12/295:10 amMDW - KOA
1 stop12h 30mSouthwest
Deal found 12/16$1,023
This Southwest deal was found by Cheapflights users on 12/16. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/269:15 pmKOA - ORD
2 stops12h 50mSouthwest
Sun 12/287:15 amORD - KOA
2 stops14h 55mSouthwest
Deal found 12/16$1,044
This Delta deal was found by Cheapflights users on 12/16. 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 12/3110:55 pmKOA - MDW
2 stops14h 24mDelta
Sun 1/49:29 amMDW - KOA
2 stops14h 06mDelta
Deal found 12/16$1,204
This Alaska Airlines deal was found by Cheapflights users on 12/16. 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.
Wed 12/312:25 pmKOA - ORD
1 stop20h 12mAlaska Airlines
Wed 1/78:00 amORD - KOA
1 stop12h 55mAlaska Airlines
Deal found 12/16$2,267
This Alaska Airlines deal was found by Cheapflights users on 12/16. 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.
Wed 12/316:16 pmKOA - ORD
2 stops16h 25mMultiple Airlines
Wed 1/78:00 amORD - KOA
1 stop12h 55mMultiple Airlines
Deal found 12/16$2,399

Find 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 December 18, 2025.

Round-trip from

$393
(Alaska Airlines)

One-way from

$211
(American Airlines)

Good one-way deal

$516 or less
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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Price to beat on a one-way flight from The Big Island to Chicago (CHI).
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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 December 18, 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

2:51 pm-11:37 pm

1 stop28h 46m

Chicago O'Hare Intl

Thu 1/22

3:44 pm-3:57 pm

1 stop28h 13m

$393

Kailua-KonaChicago

KOA - ORD

KOAORD

Kona Intl

Thu 1/15

2:51 pm-2:29 pm

1 stop19h 38m

Chicago O'Hare Intl

Thu 1/22

9:00 am-9:30 pm

2 stops16h 30m

$399

Kailua-KonaChicago

KOA - ORD

KOAORD

Kona Intl

Wed 1/14

2:51 pm-2:29 pm

1 stop19h 38m

Chicago O'Hare Intl

Sun 1/18

3:44 pm-3:57 pm

1 stop28h 13m

$413

Kailua-KonaChicago

KOA - ORD

KOAORD

Kona Intl

Sat 1/24

2:24 pm-11:37 pm

1 stop29h 13m

Chicago O'Hare Intl

Sat 1/31

3:44 pm-3:57 pm

1 stop28h 13m

$432

Kailua-KonaChicago

KOA - ORD

KOAORD

Kona Intl

Wed 1/14

6:00 am-11:50 pm

2 stops13h 50m

Chicago O'Hare Intl

Sun 1/18

3:44 pm-3:57 pm

1 stop28h 13m

$447

Kailua-KonaChicago

KOA - ORD

KOAORD

Kona Intl

Sat 1/24

2:24 pm-2:29 pm

1 stop20h 05m

Chicago O'Hare Intl

Sat 1/31

9:00 am-7:18 am

2 stops26h 18m

$461

HiloChicago

ITO - ORD

ITOORD

Hilo Intl

Thu 2/12

7:41 pm-2:58 pm

2 stops15h 17m

Chicago O'Hare Intl

Thu 2/19

8:20 am-9:24 pm

2 stops17h 04m

$474

Kailua-KonaChicago

KOA - ORD

KOAORD

Kona Intl

Wed 2/18

1:10 pm-11:59 pm

1 stop30h 49m

Chicago O'Hare Intl

Sun 2/22

3:07 pm-3:53 pm

1 stop28h 46m

$488

HiloChicago

ITO - ORD

ITOORD

Hilo Intl

Sat 2/14

6:00 am-11:59 pm

2 stops13h 59m

Chicago O'Hare Intl

Thu 2/19

8:20 am-9:24 pm

2 stops17h 04m

$496

HiloChicago

ITO - ORD

ITOORD

Hilo Intl

Thu 1/15

7:44 pm-2:29 pm

2 stops14h 45m

Chicago O'Hare Intl

Mon 1/19

2:06 pm-7:04 pm

2 stops32h 58m

$496

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/17

Showing 1-10 of 42 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, October is the cheapest month in which you can book a flight from The Big Island to Chicago (average of $447). Flying from The Big Island to Chicago in April is currently the most expensive (average of $752). 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 December 18, 2025.

Unlike in the afternoon, when flights are generally more expensive, you can save up to 58% on flights from The Big Island to Chicago by exploring options for tickets in the morning.

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 28h 46m. The distance from The Big Island to Chicago is about 4205 mi.

  • 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 $223. 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 O'Hare Intl or Kona Intl - Chicago Midway as they are the most popular.

  • What are the cheapest flights from The Big Island to Chicago?

    The cheapest flight price from The Big Island to Chicago is $362. On average you can expect to pay $632. The most popular route, (Hilo Intl - Chicago O'Hare Intl), can usually be booked for $474.

  • 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, October is the cheapest month in which you can book a flight from The Big Island to Chicago (average of $447). Flying from The Big Island to Chicago in April is currently the most expensive (average of $752). 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
Lansing
Merrillville
Hammond
Porter
Benton Harbor

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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 December 18, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$447Average$792FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$545Average$653FlexibilityNo cancel feeOn-time71%
Alaska AirlinesCheapest$555Average$979FlexibilityNo cancel feeOn-time75%
SouthwestCheapest$693Average$768FlexibilityNo cancel feeOn-time63%

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