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The Big Island

$190+ Cheap flights from Chicago (CHI) to The Big Island

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 3/17. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — KOA
Jan 27 — Feb 31
Tue 1/27
Tue 2/3
1 adult, Economy
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Cheap flight deals from Chicago to The Big Island

Cheapest flights from Chicago to The Big Island
Explore the most affordable flight options available from Chicago to The Big Island. Find the lowest fares from popular airlines and budget airlines, with prices last updated on December 28, 2025.

This Delta deal was found by Cheapflights users on 12/27. 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.
Wed 12/317:25 amORD - KOA
1 stop12h 23mDelta
Mon 1/128:45 pmKOA - ORD
1 stop12h 37mDelta
Deal found 12/27$693
This American Airlines deal was found by Cheapflights users on 12/27. 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.
Wed 12/3110:40 amORD - KOA
1 stop12h 11mAmerican Airlines
Tue 1/67:45 pmKOA - ORD
1 stop12h 10mAmerican Airlines
Deal found 12/27$753
This Delta deal was found by Cheapflights users on 12/27. 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.
Wed 12/319:29 amMDW - KOA
2 stops14h 13mDelta
Mon 1/128:45 pmKOA - MDW
2 stops16h 49mDelta
Deal found 12/27$764
This American Airlines deal was found by Cheapflights users on 12/26. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/305:21 amORD - KOA
1 stop13h 55mAmerican Airlines
Tue 1/67:45 pmKOA - ORD
1 stop11h 09mAmerican Airlines
Deal found 12/26$778
This Delta deal was found by Cheapflights users on 12/27. 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.
Tue 12/306:15 pmORD - KOA
2 stops25h 33mDelta
Mon 1/127:55 pmKOA - ORD
1 stop13h 43mDelta
Deal found 12/27$816
This Southwest deal was found by Cheapflights users on 12/27. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/295:10 amMDW - KOA
1 stop12h 30mSouthwest
Mon 1/129:25 pmKOA - MDW
1 stop11h 10mSouthwest
Deal found 12/27$818
This Delta deal was found by Cheapflights users on 12/27. 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 12/296:15 pmORD - KOA
2 stops25h 33mDelta
Mon 1/127:55 pmKOA - ORD
1 stop13h 43mDelta
Deal found 12/27$864
This Delta deal was found by Cheapflights users on 12/27. 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.
Tue 12/306:00 amMDW - KOA
2 stops18h 27mDelta
Mon 1/127:55 pmKOA - MDW
2 stops12h 53mDelta
Deal found 12/27$931
This Southwest deal was found by Cheapflights users on 12/26. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/295:10 amMDW - KOA
1 stop12h 30mSouthwest
Tue 1/67:00 pmKOA - MDW
2 stops13h 35mSouthwest
Deal found 12/26$1,008
This Expedia deal was found by Cheapflights users on 12/26. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/272:12 pmORD - MUE
2 stops20h 40mMultiple Airlines
Fri 1/29:10 pmMUE - ORD
2 stops13h 47mMultiple Airlines
Deal found 12/26$2,208

Find flight deals from Chicago to The Big Island

Keep the following information in mind while searching for Chicago to The Big Island flight deals. Data was last updated December 28, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$381
(Alaska Airlines)

One-way from

$190
(Kiwi.com)

Popular in

December

Cheapest in

September

Average price

$1,118
Provider with most accurate pricing for Chicago (CHI)-Kona Intl flight deals.
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Provider most trusted by Cheapflights users for Chicago (CHI)-Kona Intl flights.
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From Chicago (CHI) to The Big Island
Search Deals
One-way flight from Chicago (CHI) to The Big Island
Search Deals
Highest demand for flights based on searches. 8% potential increase in price ($65 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 5% potential price decrease ($36 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Chicago to The Big Island 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 28, 2025.
Use the filters below to find and compare flights from Chicago to The Big Island that are best for you.

Fly from

Chicago

Fly to

The Big Island

Route

Depart

Return

Price

ChicagoKailua-Kona

ORD - KOA

ORDKOA

Chicago O'Hare Intl

Tue 1/20

2:20 pm-6:47 pm

1 stop32h 27m

Kona Intl

Wed 1/28

8:45 pm-1:22 pm

1 stop12h 37m

$393

ChicagoKailua-Kona

ORD - KOA

ORDKOA

Chicago O'Hare Intl

Mon 1/26

7:30 am-6:47 pm

1 stop15h 17m

Kona Intl

Wed 2/4

9:55 pm-1:22 pm

1 stop11h 27m

$393

ChicagoKailua-Kona

ORD - KOA

ORDKOA

Chicago O'Hare Intl

Wed 1/21

7:30 am-6:47 pm

1 stop15h 17m

Kona Intl

Tue 1/27

8:45 pm-1:22 pm

1 stop12h 37m

$393

ChicagoKailua-Kona

ORD - KOA

ORDKOA

Chicago O'Hare Intl

Sun 2/8

7:30 am-7:57 pm

1 stop16h 27m

Kona Intl

Thu 2/19

9:55 pm-1:22 pm

1 stop11h 27m

$393

ChicagoKailua-Kona

ORD - KOA

ORDKOA

Chicago O'Hare Intl

Mon 1/26

7:30 am-6:47 pm

1 stop15h 17m

Kona Intl

Fri 2/6

9:55 pm-11:53 pm

1 stop21h 58m

$393

ChicagoKailua-Kona

ORD - KOA

ORDKOA

Chicago O'Hare Intl

Mon 1/26

7:30 am-6:47 pm

1 stop15h 17m

Kona Intl

Mon 2/2

9:55 pm-1:22 pm

1 stop11h 27m

$394

ChicagoKailua-Kona

ORD - KOA

ORDKOA

Chicago O'Hare Intl

Mon 2/2

3:35 pm-9:30 pm

1 stop33h 55m

Kona Intl

Tue 2/10

2:51 pm-2:29 pm

1 stop19h 38m

$408

ChicagoKailua-Kona

ORD - KOA

ORDKOA

Chicago O'Hare Intl

Sat 1/24

3:35 pm-9:30 pm

1 stop33h 55m

Kona Intl

Tue 2/3

2:51 pm-2:29 pm

1 stop19h 38m

$408

ChicagoKailua-Kona

ORD - KOA

ORDKOA

Chicago O'Hare Intl

Mon 2/23

3:07 pm-2:34 pm

2 stops27h 27m

Kona Intl

Tue 3/3

1:10 pm-11:59 pm

1 stop30h 49m

$412

ChicagoKailua-Kona

ORD - KOA

ORDKOA

Chicago O'Hare Intl

Tue 2/3

6:06 pm-9:30 pm

1 stop31h 24m

Kona Intl

Thu 2/5

2:51 pm-2:29 pm

1 stop19h 38m

$417

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/26

Showing 1-10 of 60 results
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Best time to book a flight from Chicago to The Big Island

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

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

Currently, March is the cheapest month in which you can book a flight from Chicago to The Big Island (average of $422). Flying from Chicago to The Big Island in July is currently the most expensive (average of $668). 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 CHI to FUI?

Find hourly flight availability from Chicago to The Big Island. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated December 28, 2025.

When flying from Chicago to The Big Island, the time of day you fly usually plays a role in the price. Save by searching for a flight at noon, which can drop the price by up to 31% versus a flight in the evening.

Reviews of airlines servicing The Big Island

Get insights into the airlines that provide service to The Big Island. 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 The Big Island. Reviews last updated December 28, 2025.
Read reviews from past customers who have flown Alaska Airlines, Southwest, and Delta from Chicago to The Big Island. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Alaska Airlines
8.0
Very good
11,551 reviews

Overall

8.0

Crew

8.5

Entertainment

7.0

Food

7.1

Boarding

8.1

Comfort

7.8

Reviews

1 / 20
10.0
Excellent

Georgana,Dec 2025

ORD - PDX

Very cordial grew. Thank you. However, crying baby issues and no ear plugs available.
Alaska Airlines
8.0
Very good
11,551 reviews
Alaska Airlines
8.0
Very good
11,551 reviews

Overall

8.0

Crew

8.5

Entertainment

7.0

Food

7.1

Boarding

8.1

Comfort

7.8

Reviews

1 / 20
10.0
Excellent

Georgana,Dec 2025

ORD - PDX

Very cordial grew. Thank you. However, crying baby issues and no ear plugs available.
Southwest
8.0
Very good
4,256 reviews
Alaska Airlines
8.0
Very good
11,551 reviews

Overall

8.0

Crew

8.5

Entertainment

7.0

Food

7.1

Boarding

8.1

Comfort

7.8

Reviews

1 / 20
10.0
Excellent

Georgana,Dec 2025

ORD - PDX

Very cordial grew. Thank you. However, crying baby issues and no ear plugs available.
Delta
7.9
Good
8,019 reviews
Alaska Airlines
8.0
Very good
11,551 reviews

Overall

8.0

Crew

8.5

Entertainment

7.0

Food

7.1

Boarding

8.1

Comfort

7.8

Reviews

1 / 20
10.0
Excellent

Georgana,Dec 2025

ORD - PDX

Very cordial grew. Thank you. However, crying baby issues and no ear plugs available.
United Airlines
7.4
Good
9,113 reviews
Alaska Airlines
8.0
Very good
11,551 reviews

Overall

8.0

Crew

8.5

Entertainment

7.0

Food

7.1

Boarding

8.1

Comfort

7.8

Reviews

1 / 20
10.0
Excellent

Georgana,Dec 2025

ORD - PDX

Very cordial grew. Thank you. However, crying baby issues and no ear plugs available.
American Airlines
7.2
Good
11,072 reviews
Alaska Airlines
8.0
Very good
11,551 reviews

Overall

8.0

Crew

8.5

Entertainment

7.0

Food

7.1

Boarding

8.1

Comfort

7.8

Reviews

1 / 20
10.0
Excellent

Georgana,Dec 2025

ORD - PDX

Very cordial grew. Thank you. However, crying baby issues and no ear plugs available.

Related info for your journey

Find useful and relevant information for your journey from Chicago to The Big Island. 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 Chicago to The Big Island?

    Departing from Chicago to The Big Island will take you 13h 35m. Chicago and The Big Island are separated by a distance of 4162 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

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

    $211 is the cheapest one-way deal found within the past few days, from Hawaiian Airlines. You may also be able to find cheap deals on Alaska Airlines and American Airlines, with prices starting from $212 and $233, respectively.

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

    The most popular flight routes from Chicago to The Big Island are Chicago O'Hare Intl - Kona Intl, Chicago Midway - Kona Intl and Chicago O'Hare Intl - Hilo Intl.

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

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

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

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

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

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

    Currently, March is the cheapest month in which you can book a flight from Chicago to The Big Island (average of $422). Flying from Chicago to The Big Island in July is currently the most expensive (average of $668). 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 Chicago to The Big Island

See prices for flight routes from nearby airports that may be better suited for you.
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Top 6 airlines flying from Chicago to The Big Island

Discover the top 6 airlines that operate flights from Chicago to The Big Island. 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 28, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$371Average$594FlexibilityNo cancel feeOn-timeN/A
Alaska AirlinesCheapest$424Average$777FlexibilityNo cancel feeOn-time75%
Hawaiian AirlinesCheapest$429Average$651FlexibilityNo cancel feeOn-time85%
United AirlinesCheapest$447Average$1,106FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$455Average$723FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$593Average$722FlexibilityNo cancel feeOn-time63%

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