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The Big Island

$211+ 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 3/1. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — KOA
feb. 18 — feb. 251
wo 2/18
wo 2/25
1 adult, Economy
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Cheap 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 januari 19, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

Expedia
3 stars

Round-trip from

$402
(Alaska Airlines)

One-way from

$211
(American Airlines)

Popular in

December

Cheapest in

September

Average price

$598

Good round-trip deal

$1,194 or less
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
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One-way flight from Chicago (CHI) to The Big Island
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Highest demand for flights based on searches. 6% potential increase in price ($53 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($33 potential savings vs. average RT price).
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Average for round-trip flights in January 2026
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Price to beat on a round-trip flight from Chicago (CHI) to The Big Island.
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Find 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 januari 19, 2026.

This Alaska Airlines deal was found by Cheapflights users on 1/17. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
zo 3/13:07 pm
ORD
-
KOA
1 stop28h 46m
Alaska Airlines
di 3/1012:10 pm
KOA
-
ORD
1 stop30h 49m
Alaska Airlines
Deal found 1/17$402
This Alaska Airlines deal was found by Cheapflights users on 1/17. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
di 4/148:20 am
ORD
-
KOA
1 stop11h 39m
Alaska Airlines
di 4/281:16 pm
KOA
-
ORD
1 stop24h 47m
Alaska Airlines
Deal found 1/17$403
This Alaska Airlines deal was found by Cheapflights users on 1/17. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
di 4/148:20 am
ORD
-
KOA
1 stop11h 39m
Multiple Airlines
di 4/286:41 pm
KOA
-
ORD
2 stops15h 00m
Multiple Airlines
Deal found 1/17$408
This Alaska Airlines deal was found by Cheapflights users on 1/17. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
di 4/148:20 am
ORD
-
KOA
1 stop11h 39m
Alaska Airlines
do 4/231:16 pm
KOA
-
ORD
1 stop24h 47m
Alaska Airlines
Deal found 1/17$413
This Kiwi.com deal was found by Cheapflights users on 1/17. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
ma 2/99:00 am
ORD
-
KOA
2 stops15h 28m
Multiple Airlines
do 2/261:10 pm
KOA
-
ORD
1 stop30h 49m
Multiple Airlines
Deal found 1/17$417
This American Airlines deal was found by Cheapflights users on 1/17. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
ma 2/95:05 am
ORD
-
KOA
1 stop14h 43m
American Airlines
do 2/2610:11 pm
KOA
-
ORD
1 stop10h 20m
American Airlines
Deal found 1/17$422
This Delta deal was found by Cheapflights users on 1/17. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
wo 4/157:00 am
ORD
-
KOA
1 stop16h 55m
Delta
di 4/288:55 pm
KOA
-
ORD
1 stop15h 11m
Delta
Deal found 1/17$424
This Alaska Airlines deal was found by Cheapflights users on 1/18. 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.
do 4/308:00 am
ORD
-
KOA
1 stop16h 52m
Alaska Airlines
ma 5/41:16 pm
KOA
-
ORD
1 stop24h 47m
Alaska Airlines
Deal found 1/18$425
This Alaska Airlines deal was found by Cheapflights users on 1/18. 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.
zo 2/89:00 am
ORD
-
KOA
2 stops15h 28m
Multiple Airlines
vr 2/1312:53 pm
KOA
-
ORD
1 stop22h 05m
Multiple Airlines
Deal found 1/18$427
This Alaska Airlines deal was found by Cheapflights users on 1/17. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
wo 4/158:20 am
ORD
-
KOA
1 stop11h 39m
Multiple Airlines
do 4/236:00 am
KOA
-
ORD
2 stops12h 43m
Multiple Airlines
Deal found 1/17$428
This Southwest deal was found by Cheapflights users on 1/16. 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.
ma 2/98:10 am
MDW
-
KOA
2 stops14h 00m
Southwest
do 2/269:25 pm
KOA
-
MDW
1 stop13h 35m
Southwest
Deal found 1/16$428
This Alaska Airlines deal was found by Cheapflights users on 1/18. 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.
vr 2/208:20 am
ORD
-
ITO
2 stops18h 15m
Multiple Airlines
wo 2/258:30 pm
ITO
-
ORD
2 stops23h 29m
Multiple Airlines
Deal found 1/18$454

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 januari 19, 2026.
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

di 4/14

8:20 am-2:59 pm

1 stop11h 39m

Kona Intl

di 4/28

6:41 pm-2:41 pm

2 stops15h 00m

$408

ChicagoKailua-Kona

MDW - KOA

MDWKOA

Chicago Midway

ma 2/9

8:10 am-6:10 pm

2 stops14h 00m

Kona Intl

do 2/26

9:25 pm-3:00 pm

1 stop13h 35m

$428

ChicagoKailua-Kona

ORD - KOA

ORDKOA

Chicago O'Hare Intl

wo 2/25

6:15 am-6:30 pm

2 stops16h 15m

Kona Intl

di 3/3

9:55 pm-1:22 pm

1 stop11h 27m

$430

ChicagoKailua-Kona

ORD - KOA

ORDKOA

Chicago O'Hare Intl

ma 3/2

8:20 am-7:17 am

2 stops26h 57m

Kona Intl

wo 3/4

10:17 pm-2:11 pm

1 stop11h 54m

$434

ChicagoKailua-Kona

ORD - KOA

ORDKOA

Chicago O'Hare Intl

wo 4/15

7:20 am-6:55 pm

2 stops16h 35m

Kona Intl

di 4/28

9:55 pm-9:35 pm

2 stops18h 40m

$435

ChicagoKailua-Kona

ORD - KOA

ORDKOA

Chicago O'Hare Intl

wo 4/15

7:20 am-6:55 pm

2 stops16h 35m

Kona Intl

wo 4/22

9:55 pm-6:04 pm

2 stops15h 09m

$435

ChicagoKailua-Kona

ORD - KOA

ORDKOA

Chicago O'Hare Intl

wo 2/25

6:15 am-6:30 pm

2 stops16h 15m

Kona Intl

wo 3/4

9:55 pm-1:22 pm

1 stop11h 27m

$452

ChicagoKailua-Kona

ORD - KOA

ORDKOA

Chicago O'Hare Intl

do 4/16

8:50 am-5:43 pm

2 stops13h 53m

Kona Intl

di 4/28

8:55 pm-5:06 pm

1 stop15h 11m

$452

ChicagoHilo

ORD - ITO

ORDITO

Chicago O'Hare Intl

vr 2/20

8:20 am-10:35 pm

2 stops18h 15m

Hilo Intl

wo 2/25

8:30 pm-11:59 pm

2 stops23h 29m

$454

ChicagoKailua-Kona

ORD - KOA

ORDKOA

Chicago O'Hare Intl

ma 2/9

7:20 am-6:30 pm

2 stops15h 10m

Kona Intl

do 2/26

10:55 pm-9:52 pm

2 stops18h 57m

$457

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/18

Showing 1-10 of 52 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 $371). Flying from Chicago to The Big Island in July is currently the most expensive (average of $665). 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 januari 19, 2026.

When flying from Chicago to The Big Island, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

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 januari 19, 2026.
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
11,745 reviews

Overall

8.0

Food

7.1

Boarding

8.1

Entertainment

7.0

Crew

8.5

Comfort

7.8

Reviews

1 / 20
10.0
Excellent

Anonymous,Jan 2026

STS - LAX

Enjoyed staff assistance from ticking thru tsa , boarding and in the plane Couldn’t pick a seat except upgrading
Alaska Airlines
8.0
Very good
11,745 reviews
Alaska Airlines
8.0
Very good
11,745 reviews

Overall

8.0

Food

7.1

Boarding

8.1

Entertainment

7.0

Crew

8.5

Comfort

7.8

Reviews

1 / 20
10.0
Excellent

Anonymous,Jan 2026

STS - LAX

Enjoyed staff assistance from ticking thru tsa , boarding and in the plane Couldn’t pick a seat except upgrading
Southwest
8.0
Very good
4,262 reviews
Alaska Airlines
8.0
Very good
11,745 reviews

Overall

8.0

Food

7.1

Boarding

8.1

Entertainment

7.0

Crew

8.5

Comfort

7.8

Reviews

1 / 20
10.0
Excellent

Anonymous,Jan 2026

STS - LAX

Enjoyed staff assistance from ticking thru tsa , boarding and in the plane Couldn’t pick a seat except upgrading
Delta
7.9
Good
8,075 reviews
Alaska Airlines
8.0
Very good
11,745 reviews

Overall

8.0

Food

7.1

Boarding

8.1

Entertainment

7.0

Crew

8.5

Comfort

7.8

Reviews

1 / 20
10.0
Excellent

Anonymous,Jan 2026

STS - LAX

Enjoyed staff assistance from ticking thru tsa , boarding and in the plane Couldn’t pick a seat except upgrading
United Airlines
7.4
Good
9,176 reviews
Alaska Airlines
8.0
Very good
11,745 reviews

Overall

8.0

Food

7.1

Boarding

8.1

Entertainment

7.0

Crew

8.5

Comfort

7.8

Reviews

1 / 20
10.0
Excellent

Anonymous,Jan 2026

STS - LAX

Enjoyed staff assistance from ticking thru tsa , boarding and in the plane Couldn’t pick a seat except upgrading
American Airlines
7.2
Good
11,160 reviews
Alaska Airlines
8.0
Very good
11,745 reviews

Overall

8.0

Food

7.1

Boarding

8.1

Entertainment

7.0

Crew

8.5

Comfort

7.8

Reviews

1 / 20
10.0
Excellent

Anonymous,Jan 2026

STS - LAX

Enjoyed staff assistance from ticking thru tsa , boarding and in the plane Couldn’t pick a seat except upgrading

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 14h. Chicago and The Big Island are separated by a distance of 4213 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?

    $195 is the cheapest one-way deal found within the past few days, from Alaska Airlines. You may also be able to find cheap deals on Hawaiian Airlines and American Airlines, with prices starting from $211 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 $371). Flying from Chicago to The Big Island in July is currently the most expensive (average of $665). 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

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

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 januari 19, 2026.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$343Average$577FlexibilityNo cancel feeOn-timeN/A
Alaska AirlinesCheapest$419Average$781FlexibilityNo cancel feeOn-time75%
Hawaiian AirlinesCheapest$429Average$651FlexibilityNo cancel feeOn-time85%
United AirlinesCheapest$447Average$1,115FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$453Average$711FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$578Average$696FlexibilityNo cancel feeOn-time63%

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