HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Chicago

$202+ 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 2/12. Fares are subject to change and may not be available on all flights or dates of travel.
KOA — CHI
Dec 4 — Dec 111
Thu 12/4
Thu 12/11
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from The Big Island to Chicago with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

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 November 4, 2025.

This Delta deal was found by Cheapflights users on 11/4. 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.
Tue 12/239:55 pmKOA - ORD
1 stop11h 25mDelta
Mon 12/297:00 amORD - KOA
2 stops15h 31mDelta
Deal found 11/4$603
This Alaska Airlines deal was found by Cheapflights users on 11/4. 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 12/232:25 pmKOA - ORD
1 stop25h 37mAlaska Airlines
Mon 12/298:58 pmORD - KOA
1 stop23h 07mAlaska Airlines
Deal found 11/4$638
This Alaska Airlines deal was found by Cheapflights users on 11/4. 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 11/198:45 amKOA - ORD
1 stop11h 39mAlaska Airlines
Sun 11/238:00 amORD - KOA
2 stops18h 21mAlaska Airlines
Deal found 11/4$829
This Delta deal was found by Cheapflights users on 11/4. 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.
Tue 12/2310:55 pmKOA - MDW
2 stops14h 24mDelta
Mon 12/296:00 amMDW - KOA
2 stops18h 27mDelta
Deal found 11/4$866
This Alaska Airlines deal was found by Cheapflights users on 11/3. 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 12/232:25 pmKOA - ORD
1 stop20h 12mAlaska Airlines
Sat 12/278:58 pmORD - KOA
2 stops23h 15mAlaska Airlines
Deal found 11/3$937
This American Airlines deal was found by Cheapflights users on 11/3. 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.
Tue 12/234:24 pmKOA - ORD
1 stop10h 35mAmerican Airlines
Sat 12/2710:40 amORD - KOA
1 stop12h 11mAmerican Airlines
Deal found 11/3$954
This Alaska Airlines deal was found by Cheapflights users on 11/2. 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 11/188:26 amITO - ORD
2 stops25h 28mAlaska Airlines
Sat 11/226:00 amORD - ITO
2 stops20h 24mAlaska Airlines
Deal found 11/2$1,040
This Alaska Airlines deal was found by Cheapflights users on 11/4. 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 11/197:43 pmITO - ORD
2 stops20h 12mAlaska Airlines
Sun 11/238:00 amORD - ITO
2 stops16h 28mAlaska Airlines
Deal found 11/4$1,269
This United Airlines deal was found by Cheapflights users on 11/4. 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
Sun 11/234:40 pmORD - ITO
2 stops31h 48mUnited Airlines
Deal found 11/4$1,331
This United Airlines deal was found by Cheapflights users on 11/4. 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.
Tue 11/187:43 pmITO - ORD
1 stop30h 25mUnited Airlines
Fri 11/217:10 amORD - ITO
2 stops17h 18mUnited Airlines
Deal found 11/4$1,390
This Delta deal was found by Cheapflights users on 11/3. 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.
Tue 12/2310:55 pmKOA - MDW
2 stops14h 24mDelta
Sat 12/276:00 amMDW - KOA
2 stops17h 23mDelta
Deal found 11/3$1,420
This American Airlines deal was found by Cheapflights users on 11/4. 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 26mAmerican Airlines
Sun 11/2310:00 amORD - ITO
1 stop11h 27mAmerican Airlines
Deal found 11/4$1,422

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 November 4, 2025.

Round-trip from

$379
(Alaska Airlines)

One-way from

$202
(Kiwi.com)

Good one-way deal

$376 or less
From The Big Island to Chicago (CHI)
Search Deals
One-way flight from The Big Island to Chicago (CHI)
Search Deals
Price to beat on a one-way flight from The Big Island to Chicago (CHI).
Search Deals

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 November 4, 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

Tue 3/3

6:00 am-11:10 pm

2 stops13h 10m

Chicago O'Hare Intl

Wed 3/4

2:59 pm-2:46 pm

1 stop27h 47m

$379

Kailua-KonaChicago

KOA - ORD

KOAORD

Kona Intl

Thu 2/12

6:00 am-11:10 pm

2 stops13h 10m

Chicago O'Hare Intl

Wed 2/18

2:59 pm-2:46 pm

1 stop27h 47m

$389

Kailua-KonaChicago

KOA - MDW

KOAMDW

Kona Intl

Thu 2/12

8:59 pm-6:37 pm

2 stops17h 38m

Chicago Midway

Wed 2/18

9:34 am-7:34 pm

2 stops14h 00m

$601

Kailua-KonaChicago

KOA - MDW

KOAMDW

Kona Intl

Thu 2/12

9:25 pm-3:00 pm

1 stop13h 35m

Chicago Midway

Wed 2/18

5:05 am-6:10 pm

2 stops17h 05m

$654

HiloChicago

ITO - ORD

ITOORD

Hilo Intl

Tue 4/21

6:00 am-11:10 pm

2 stops12h 10m

Chicago O'Hare Intl

Thu 4/23

10:00 am-9:56 pm

2 stops16h 56m

$684

Kailua-KonaChicago

KOA - MDW

KOAMDW

Kona Intl

Tue 12/23

10:55 pm-5:19 pm

2 stops14h 24m

Chicago Midway

Mon 12/29

6:00 am-8:27 pm

2 stops18h 27m

$866

HiloChicago

ITO - ORD

ITOORD

Hilo Intl

Tue 4/21

2:40 pm-6:25 am

1 stop10h 45m

Chicago O'Hare Intl

Thu 4/23

12:45 pm-9:56 pm

2 stops14h 11m

$902

Kailua-KonaChicago

KOA - MDW

KOAMDW

Kona Intl

Wed 11/19

1:45 pm-9:01 am

2 stops15h 16m

Chicago Midway

Sun 11/23

6:00 am-7:17 pm

2 stops17h 17m

$1,104

HiloChicago

ITO - ORD

ITOORD

Hilo Intl

Wed 11/19

7:43 pm-7:55 pm

2 stops20h 12m

Chicago O'Hare Intl

Sun 11/23

8:00 am-8:28 pm

2 stops16h 28m

$1,269

HiloChicago

ITO - ORD

ITOORD

Hilo Intl

Wed 11/19

7:43 pm-6:08 am

1 stop30h 25m

Chicago O'Hare Intl

Sun 11/23

4:40 pm-8:28 pm

2 stops31h 48m

$1,331

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/2

Showing 1-10 of 39 results
1
2
3
4

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, December is the cheapest month in which you can book a flight from The Big Island to Chicago (average of $429). 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 November 4, 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 13h 10m. The distance from The Big Island to Chicago is about 4205 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 Alaska Airlines, with whom users have recently found tickets for as low as $207. However, be on the lookout for offers from Southwest 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 Kona Intl - Chicago O'Hare Intl, Hilo 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 $296. On average you can expect to pay $476. The most popular route, (Kona Intl - Chicago O'Hare Intl), can usually be booked for $459.

  • 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, December is the cheapest month in which you can book a flight from The Big Island to Chicago (average of $429). 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
Merrillville
Lansing
Hammond
Porter
Benton Harbor

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

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 November 4, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$447Average$718FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$545Average$721FlexibilityNo cancel feeOn-time71%
Alaska AirlinesCheapest$555Average$1,039FlexibilityNo cancel feeOn-time75%
SouthwestCheapest$693Average$768FlexibilityNo cancel feeOn-time63%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.