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The Big Island

$199+ 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 2/18. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — KOA
Feb 20 — Feb 271
Fri 2/20
Fri 2/27
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 January 21, 2026.

This Delta deal was found by Cheapflights users on 1/20. 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 3/97:25 am
ORD
-
KOA
1 stop16h 12m
Delta
Wed 3/188:55 pm
KOA
-
ORD
1 stop11h 30m
Delta
Deal found 1/20$364
This Delta deal was found by Cheapflights users on 1/21. 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 2/187:40 am
ORD
-
KOA
2 stops14h 50m
Delta
Wed 2/259:55 pm
KOA
-
ORD
1 stop11h 27m
Delta
Deal found 1/21$370
This Delta deal was found by Cheapflights users on 1/21. 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 4/307:00 am
ORD
-
KOA
1 stop16h 55m
Delta
Mon 5/48:55 pm
KOA
-
ORD
1 stop11h 30m
Delta
Deal found 1/21$394
This Delta deal was found by Cheapflights users on 1/20. 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.
Fri 4/247:00 am
ORD
-
KOA
1 stop16h 55m
Delta
Sun 5/38:55 pm
KOA
-
ORD
1 stop11h 30m
Delta
Deal found 1/20$401
This Alaska Airlines deal was found by Cheapflights users on 1/20. 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.
Mon 3/27:00 am
ORD
-
KOA
1 stop19h 57m
Alaska Airlines
Thu 3/51:10 pm
KOA
-
ORD
1 stop30h 49m
Alaska Airlines
Deal found 1/20$403
This Delta deal was found by Cheapflights users on 1/20. 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 3/27:40 am
ORD
-
KOA
2 stops14h 50m
Delta
Thu 3/59:55 pm
KOA
-
ORD
1 stop11h 27m
Delta
Deal found 1/20$410
This Alaska Airlines deal was found by Cheapflights users on 1/21. 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 2/187:00 am
ORD
-
KOA
1 stop19h 57m
Alaska Airlines
Wed 2/251:10 pm
KOA
-
ORD
1 stop30h 49m
Alaska Airlines
Deal found 1/21$413
This Expedia deal was found by Cheapflights users on 1/20. 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.
Mon 3/28:20 am
ORD
-
KOA
2 stops17h 55m
Multiple Airlines
Wed 3/41:10 pm
KOA
-
ORD
1 stop21h 48m
Multiple Airlines
Deal found 1/20$418
This American 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 2/87:00 am
ORD
-
KOA
1 stop11h 54m
American Airlines
Fri 2/1310:11 pm
KOA
-
ORD
1 stop10h 20m
American Airlines
Deal found 1/18$422
This American Airlines deal was found by Cheapflights users on 1/19. 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.
Mon 2/96:00 am
ORD
-
KOA
1 stop12h 54m
American Airlines
Fri 2/1310:11 pm
KOA
-
ORD
1 stop12h 42m
American Airlines
Deal found 1/19$424
This Southwest deal was found by Cheapflights users on 1/20. 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 3/27:55 am
MDW
-
KOA
2 stops17h 25m
Southwest
Wed 3/49:25 pm
KOA
-
MDW
2 stops12h 50m
Southwest
Deal found 1/20$433
This Expedia deal was found by Cheapflights users on 1/21. 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.
Tue 3/108:20 am
ORD
-
ITO
2 stops18h 04m
Multiple Airlines
Tue 3/177:36 pm
ITO
-
ORD
2 stops17h 50m
Multiple Airlines
Deal found 1/21$436

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 January 21, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

Expedia
3 stars

Round-trip from

$364
(Delta)

One-way from

$199
(Kiwi.com)

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.
Search Deals
Provider most trusted by Cheapflights users for Chicago (CHI)-Kona Intl flights.
Search Deals
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. 6% potential increase in price ($53 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease ($33 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 2026
Search Deals
Price to beat on a round-trip flight from Chicago (CHI) to The Big Island.
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 January 21, 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

Mon 3/9

7:25 am-6:37 pm

1 stop16h 12m

Kona Intl

Wed 3/18

8:55 pm-1:25 pm

1 stop11h 30m

$364

ChicagoKailua-Kona

ORD - KOA

ORDKOA

Chicago O'Hare Intl

Thu 2/19

7:15 am-3:51 pm

1 stop12h 36m

Kona Intl

Tue 2/24

9:55 pm-1:22 pm

1 stop11h 27m

$444

ChicagoKailua-Kona

ORD - KOA

ORDKOA

Chicago O'Hare Intl

Mon 3/2

8:20 am-8:13 am

2 stops27h 53m

Kona Intl

Wed 3/4

9:01 pm-4:33 pm

2 stops15h 32m

$449

ChicagoKailua-Kona

ORD - KOA

ORDKOA

Chicago O'Hare Intl

Fri 2/20

7:00 am-10:57 pm

1 stop19h 57m

Kona Intl

Wed 2/25

1:10 pm-2:58 pm

1 stop21h 48m

$451

ChicagoHilo

ORD - ITO

ORDITO

Chicago O'Hare Intl

Fri 2/20

8:20 am-10:35 pm

2 stops18h 15m

Hilo Intl

Wed 2/25

8:30 pm-11:59 pm

2 stops23h 29m

$454

ChicagoKailua-Kona

MDW - KOA

MDWKOA

Chicago Midway

Mon 3/2

7:55 am-9:20 pm

2 stops17h 25m

Kona Intl

Wed 3/4

9:25 pm-1:35 pm

1 stop12h 10m

$459

ChicagoKailua-Kona

ORD - KOA

ORDKOA

Chicago O'Hare Intl

Fri 2/27

8:20 am-7:17 am

2 stops26h 57m

Kona Intl

Wed 3/4

1:10 pm-11:59 pm

1 stop30h 49m

$465

ChicagoKailua-Kona

ORD - KOA

ORDKOA

Chicago O'Hare Intl

Mon 2/9

7:20 am-6:30 pm

2 stops15h 10m

Kona Intl

Fri 2/13

10:55 pm-4:41 pm

2 stops13h 46m

$465

ChicagoKailua-Kona

MDW - KOA

MDWKOA

Chicago Midway

Fri 2/20

7:45 am-6:10 pm

2 stops14h 25m

Kona Intl

Wed 2/25

9:25 pm-3:05 pm

2 stops13h 40m

$486

ChicagoKailua-Kona

MDW - KOA

MDWKOA

Chicago Midway

Thu 2/26

7:45 am-6:10 pm

2 stops14h 25m

Kona Intl

Wed 3/4

9:25 pm-1:35 pm

1 stop12h 10m

$487

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/20

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 $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 January 21, 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 January 21, 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
11,775 reviews

Boarding

8.1

Overall

8.0

Entertainment

7.0

Comfort

7.8

Crew

8.5

Food

7.1

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
11,775 reviews
Alaska Airlines
8.0
Very good
11,775 reviews

Boarding

8.1

Overall

8.0

Entertainment

7.0

Comfort

7.8

Crew

8.5

Food

7.1

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
4,266 reviews
Alaska Airlines
8.0
Very good
11,775 reviews

Boarding

8.1

Overall

8.0

Entertainment

7.0

Comfort

7.8

Crew

8.5

Food

7.1

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
8,089 reviews
Alaska Airlines
8.0
Very good
11,775 reviews

Boarding

8.1

Overall

8.0

Entertainment

7.0

Comfort

7.8

Crew

8.5

Food

7.1

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
9,191 reviews
Alaska Airlines
8.0
Very good
11,775 reviews

Boarding

8.1

Overall

8.0

Entertainment

7.0

Comfort

7.8

Crew

8.5

Food

7.1

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
11,174 reviews
Alaska Airlines
8.0
Very good
11,775 reviews

Boarding

8.1

Overall

8.0

Entertainment

7.0

Comfort

7.8

Crew

8.5

Food

7.1

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 16h 12m. Chicago and The Big Island are separated by a distance of 4205 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.

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

    While on average a flight from Chicago to The Big Island is generally $1,392, our data shows the cheapest flight currently is $1,183. When looking at the most popular route, (Chicago O'Hare Intl - Kona Intl), you can expect to pay $364 for that flight.

  • 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

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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.
O'Hare Intl to Honolulu flights
O'Hare Intl to Kahului flights
Midway to Honolulu flights
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Midway to Kahului flights
St. Louis to Kailua-Kona flights
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Midway to Kailua-Kona flights
Midway to Lihue flights
O'Hare Intl to Hilo flights
St. Louis to Lihue flights
Midway to Hilo flights
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Peoria to Honolulu flights
St. Louis to Hilo flights
Evansville to Honolulu flights
Moline to Kailua-Kona flights
Moline to Honolulu flights
Peoria to Kahului flights
Bloomington to Honolulu flights
Moline to Lihue flights
Bloomington to Kahului flights
Bloomington to Lihue flights
Peoria to Lihue flights
O'Hare Intl to Waimea (Big Island) flights
Springfield to Honolulu flights
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O'Hare Intl to Kapalua flights
Decatur to Honolulu flights
Champaign to Honolulu flights
O'Hare Intl to Hana flights
St. Louis to Kapalua flights
Evansville to Kahului flights
St. Louis to Waimea (Big Island) flights
St. Louis to Hana flights
Champaign to Kailua-Kona flights
Springfield to Kahului flights
Springfield to Lihue flights
Dubuque to Honolulu flights
Evansville to Lihue flights

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 January 21, 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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