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The Big Island

$171+ 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 3/10. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — KOA
feb. 28 — mar. 71
sáb. 2/28
sáb. 3/7
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 enero 29, 2026.

This Alaska Airlines deal was found by Cheapflights users on 1/26. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 4/293:52 pm
ORD
-
KOA
1 stop28h 04m
Alaska Airlines
lun. 5/41:16 pm
KOA
-
ORD
1 stop24h 47m
Alaska Airlines
Deal found 1/26$382
This Alaska Airlines deal was found by Cheapflights users on 1/26. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 4/293:52 pm
ORD
-
KOA
1 stop28h 04m
Alaska Airlines
mié. 5/61:16 pm
KOA
-
ORD
1 stop24h 47m
Alaska Airlines
Deal found 1/26$392
This Alaska Airlines deal was found by Cheapflights users on 1/26. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 4/288:50 am
ORD
-
KOA
2 stops18h 26m
Multiple Airlines
lun. 5/41:16 pm
KOA
-
ORD
1 stop24h 47m
Multiple Airlines
Deal found 1/26$398
This Alaska Airlines deal was found by Cheapflights users on 1/26. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 4/277:59 pm
ORD
-
KOA
1 stop23h 57m
Alaska Airlines
jue. 5/71:16 pm
KOA
-
ORD
1 stop18h 57m
Alaska Airlines
Deal found 1/26$402
This Alaska Airlines deal was found by Cheapflights users on 1/28. 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.
mar. 2/243:07 pm
ORD
-
KOA
1 stop28h 46m
Alaska Airlines
mar. 3/31:10 pm
KOA
-
ORD
1 stop21h 48m
Alaska Airlines
Deal found 1/28$403
This Alaska Airlines deal was found by Cheapflights users on 1/26. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 4/288:50 am
ORD
-
KOA
2 stops18h 26m
Multiple Airlines
mié. 5/61:16 pm
KOA
-
ORD
1 stop24h 47m
Multiple Airlines
Deal found 1/26$408
This Alaska Airlines deal was found by Cheapflights users on 1/26. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom. 5/37:59 pm
ORD
-
KOA
1 stop23h 57m
Alaska Airlines
jue. 5/71:16 pm
KOA
-
ORD
1 stop24h 47m
Alaska Airlines
Deal found 1/26$412
This Alaska Airlines deal was found by Cheapflights users on 1/28. 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.
lun. 2/233:07 pm
ORD
-
KOA
1 stop28h 46m
Alaska Airlines
mar. 3/31:10 pm
KOA
-
ORD
1 stop21h 48m
Alaska Airlines
Deal found 1/28$413
This Alaska Airlines deal was found by Cheapflights users on 1/28. 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.
mar. 2/248:20 am
ORD
-
KOA
2 stops26h 57m
Multiple Airlines
mar. 3/37:50 pm
KOA
-
ORD
2 stops24h 09m
Multiple Airlines
Deal found 1/28$415
This Kiwi.com deal was found by Cheapflights users on 1/28. 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.
lun. 3/21:00 pm
ORD
-
KOA
1 stop13h 57m
Multiple Airlines
mar. 3/109:01 pm
KOA
-
ORD
2 stops12h 57m
Multiple Airlines
Deal found 1/28$416
This Kiwi.com deal was found by Cheapflights users on 1/28. 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.
mié. 2/258:20 am
ORD
-
KOA
2 stops17h 55m
Multiple Airlines
mié. 3/410:17 pm
KOA
-
ORD
1 stop11h 54m
Multiple Airlines
Deal found 1/28$417
This Alaska Airlines deal was found by Cheapflights users on 1/26. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 4/278:50 am
ORD
-
KOA
2 stops18h 26m
Multiple Airlines
jue. 5/71:16 pm
KOA
-
ORD
1 stop24h 47m
Multiple Airlines
Deal found 1/26$418

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 enero 29, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$382
(Alaska Airlines)

One-way from

$171
(Kiwi.com)

Popular in

December

Cheapest in

September

Average price

$593
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 ($51 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease ($32 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 2026
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 enero 29, 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

mar. 4/28

8:50 am-10:16 pm

2 stops18h 26m

Kona Intl

lun. 5/4

1:16 pm-7:03 pm

1 stop24h 47m

$398

ChicagoKailua-Kona

ORD - KOA

ORDKOA

Chicago O'Hare Intl

lun. 4/27

3:52 pm-2:56 pm

1 stop28h 04m

Kona Intl

mié. 5/6

1:16 pm-7:03 pm

1 stop24h 47m

$402

ChicagoKailua-Kona

ORD - KOA

ORDKOA

Chicago O'Hare Intl

mar. 2/24

3:07 pm-3:53 pm

1 stop28h 46m

Kona Intl

mar. 3/3

4:27 pm-2:58 pm

2 stops18h 31m

$408

ChicagoKailua-Kona

ORD - KOA

ORDKOA

Chicago O'Hare Intl

lun. 3/2

3:07 pm-3:53 pm

1 stop28h 46m

Kona Intl

mié. 3/4

10:17 pm-2:11 pm

1 stop11h 54m

$422

ChicagoKailua-Kona

ORD - KOA

ORDKOA

Chicago O'Hare Intl

mar. 4/28

7:15 am-7:03 pm

1 stop16h 48m

Kona Intl

jue. 5/7

9:45 pm-5:22 pm

1 stop14h 37m

$424

ChicagoKailua-Kona

ORD - KOA

ORDKOA

Chicago O'Hare Intl

mar. 4/28

7:15 am-7:03 pm

1 stop16h 48m

Kona Intl

mar. 5/5

8:50 pm-4:39 pm

1 stop14h 49m

$424

ChicagoKailua-Kona

ORD - KOA

ORDKOA

Chicago O'Hare Intl

lun. 3/2

3:07 pm-3:53 pm

1 stop28h 46m

Kona Intl

mié. 3/4

6:56 pm-2:11 pm

2 stops15h 15m

$428

ChicagoKailua-Kona

ORD - KOA

ORDKOA

Chicago O'Hare Intl

mié. 4/15

8:00 am-5:31 pm

1 stop14h 31m

Kona Intl

jue. 4/23

6:00 am-11:43 pm

2 stops12h 43m

$428

ChicagoKailua-Kona

ORD - KOA

ORDKOA

Chicago O'Hare Intl

lun. 4/27

8:50 am-10:16 pm

2 stops18h 26m

Kona Intl

mar. 5/5

1:16 pm-7:03 pm

1 stop24h 47m

$428

ChicagoKailua-Kona

ORD - KOA

ORDKOA

Chicago O'Hare Intl

mié. 4/29

7:15 am-7:03 pm

1 stop16h 48m

Kona Intl

mar. 5/5

8:50 pm-6:13 pm

2 stops16h 23m

$430

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/27

Showing 1-10 of 54 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 $374). 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 enero 29, 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 enero 29, 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
11,807 reviews

Entertainment

7.0

Crew

8.5

Comfort

7.8

Overall

8.0

Boarding

8.1

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
11,807 reviews
Alaska Airlines
8.0
Very good
11,807 reviews

Entertainment

7.0

Crew

8.5

Comfort

7.8

Overall

8.0

Boarding

8.1

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
4,267 reviews
Alaska Airlines
8.0
Very good
11,807 reviews

Entertainment

7.0

Crew

8.5

Comfort

7.8

Overall

8.0

Boarding

8.1

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
8,128 reviews
Alaska Airlines
8.0
Very good
11,807 reviews

Entertainment

7.0

Crew

8.5

Comfort

7.8

Overall

8.0

Boarding

8.1

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
9,215 reviews
Alaska Airlines
8.0
Very good
11,807 reviews

Entertainment

7.0

Crew

8.5

Comfort

7.8

Overall

8.0

Boarding

8.1

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
11,205 reviews
Alaska Airlines
8.0
Very good
11,807 reviews

Entertainment

7.0

Crew

8.5

Comfort

7.8

Overall

8.0

Boarding

8.1

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 13h 20m. 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 $374). 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

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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
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St. Louis to Kahului flights
St. Louis to Kailua-Kona flights
Midway to Lihue flights
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O'Hare Intl to Hilo flights
Midway to Hilo flights
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Evansville to Honolulu flights
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Moline to Honolulu flights
Moline to Kailua-Kona flights
Peoria to Kahului flights
Bloomington to Honolulu flights
Decatur to Honolulu flights
Moline to Lihue flights
Bloomington to Kahului flights
Bloomington to Lihue flights
Champaign to Honolulu flights
O'Hare Intl to Waimea (Big Island) flights
Peoria to Lihue flights
Springfield to Honolulu flights
Springfield to Kahului flights
O'Hare Intl to Kapalua flights
Evansville to Lihue flights
Dubuque to Honolulu flights
St. Louis to Kapalua flights
St. Louis to Waimea (Big Island) flights
Evansville to Kahului flights
St. Louis to Hana flights
Springfield to Lihue flights
Moline to Hilo flights
O'Hare Intl to Hana flights
Champaign to Kailua-Kona 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 enero 29, 2026.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$265Average$577FlexibilityNo cancel feeOn-timeN/A
Alaska AirlinesCheapest$419Average$777FlexibilityNo cancel feeOn-time75%
Hawaiian AirlinesCheapest$429Average$632FlexibilityNo cancel feeOn-time85%
United AirlinesCheapest$447Average$1,099FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$453Average$711FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$578Average$696FlexibilityNo cancel feeOn-time63%

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