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The Big Island

$219+ 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 9/23. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — KOA
ago. 30 — sep. 61
sáb. 8/30
sáb. 9/6
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 agosto 25, 2025.

Round-trip from

$417
(Alaska Airlines)

One-way from

$219
(Kiwi.com)

Popular in

March

Cheapest in

September

Average price

$661
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. 2% potential increase in price ($20 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($23 potential savings vs. average RT price).
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Average for round-trip flights in August 2025
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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 agosto 25, 2025.

This Alaska Airlines deal was found by Cheapflights users on 8/23. 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. 12/37:59 pmORD - ITO
2 stops30h 37mAlaska Airlines
jue. 12/1110:56 amITO - ORD
2 stops15h 25mAlaska Airlines
Deal found 8/23$417
This Alaska Airlines deal was found by Cheapflights users on 8/23. 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.
jue. 12/43:05 pmORD - KOA
2 stops25h 50mAlaska Airlines
lun. 12/152:20 pmKOA - ORD
1 stop19h 49mAlaska Airlines
Deal found 8/23$440
This Alaska Airlines deal was found by Cheapflights users on 8/25. 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. 10/282:54 pmORD - KOA
1 stop27h 49mAlaska Airlines
mar. 11/412:09 pmKOA - ORD
1 stop26h 50mAlaska Airlines
Deal found 8/25$445
This Alaska Airlines deal was found by Cheapflights users on 8/23. 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.
jue. 10/238:00 amORD - KOA
1 stop12h 57mAlaska Airlines
mar. 10/2811:09 amKOA - ORD
1 stop26h 50mAlaska Airlines
Deal found 8/23$446
This Delta deal was found by Cheapflights users on 8/25. 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.
mié. 9/177:10 amORD - KOA
1 stop15h 19mDelta
mié. 9/249:30 pmKOA - ORD
1 stop10h 50mDelta
Deal found 8/25$447
This Alaska Airlines deal was found by Cheapflights users on 8/25. 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. 11/127:59 pmORD - ITO
2 stops30h 20mAlaska Airlines
mar. 11/187:43 pmITO - ORD
2 stops14h 11mAlaska Airlines
Deal found 8/25$457
This Alaska Airlines deal was found by Cheapflights users on 8/25. 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. 10/228:00 amORD - ITO
2 stops17h 31mAlaska Airlines
mié. 10/296:00 amITO - ORD
2 stops13h 24mAlaska Airlines
Deal found 8/25$458
This Delta deal was found by Cheapflights users on 8/23. 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.
mié. 10/87:37 amORD - KOA
2 stops16h 46mDelta
mié. 10/229:30 pmKOA - ORD
1 stop11h 00mDelta
Deal found 8/23$467
This United Airlines deal was found by Cheapflights users on 8/24. 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.
jue. 9/257:10 amORD - KOA
1 stop13h 36mUnited Airlines
lun. 9/291:05 pmKOA - ORD
1 stop11h 01mUnited Airlines
Deal found 8/24$471
This Delta deal was found by Cheapflights users on 8/25. 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.
mar. 10/286:08 amORD - KOA
2 stops16h 22mDelta
mar. 11/49:30 pmKOA - ORD
2 stops15h 40mDelta
Deal found 8/25$472
This Alaska Airlines deal was found by Cheapflights users on 8/23. 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.
sáb. 10/1810:00 amORD - KOA
1 stop31h 29mAlaska Airlines
mar. 10/2811:09 amKOA - ORD
1 stop21h 45mAlaska Airlines
Deal found 8/23$475
This Alaska Airlines deal was found by Cheapflights users on 8/23. 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.
vie. 10/3110:00 amORD - KOA
1 stop11h 44mAlaska Airlines
lun. 11/1012:09 pmKOA - ORD
1 stop26h 50mAlaska Airlines
Deal found 8/23$476

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 agosto 25, 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

ChicagoHilo

ORD - ITO

ORDITO

Chicago O'Hare Intl

mié. 12/3

7:59 pm-10:36 pm

2 stops30h 37m

Hilo Intl

jue. 12/11

10:56 am-6:21 am

2 stops15h 25m

$417

ChicagoKailua-Kona

ORD - KOA

ORDKOA

Chicago O'Hare Intl

jue. 12/4

3:05 pm-12:55 pm

2 stops25h 50m

Kona Intl

lun. 12/15

2:20 pm-2:09 pm

1 stop19h 49m

$440

ChicagoKailua-Kona

ORD - KOA

ORDKOA

Chicago O'Hare Intl

mar. 10/28

2:54 pm-1:43 pm

1 stop27h 49m

Kona Intl

mar. 11/4

12:09 pm-6:59 pm

1 stop26h 50m

$445

ChicagoKailua-Kona

ORD - KOA

ORDKOA

Chicago O'Hare Intl

jue. 10/23

8:00 am-3:57 pm

1 stop12h 57m

Kona Intl

mar. 10/28

11:09 am-6:59 pm

1 stop26h 50m

$446

ChicagoKailua-Kona

ORD - KOA

ORDKOA

Chicago O'Hare Intl

mié. 9/24

10:49 am-7:24 pm

1 stop13h 35m

Kona Intl

mié. 10/1

7:40 pm-1:12 pm

1 stop12h 32m

$447

ChicagoKailua-Kona

ORD - KOA

ORDKOA

Chicago O'Hare Intl

mié. 9/17

7:10 am-5:29 pm

1 stop15h 19m

Kona Intl

mié. 9/24

9:30 pm-1:20 pm

1 stop10h 50m

$447

ChicagoKailua-Kona

ORD - KOA

ORDKOA

Chicago O'Hare Intl

jue. 9/25

7:10 am-5:29 pm

1 stop15h 19m

Kona Intl

lun. 9/29

9:30 pm-1:20 pm

1 stop10h 50m

$447

ChicagoKailua-Kona

ORD - KOA

ORDKOA

Chicago O'Hare Intl

jue. 12/4

7:10 am-4:18 pm

1 stop13h 08m

Kona Intl

lun. 12/15

2:15 pm-6:19 am

1 stop12h 04m

$447

ChicagoKailua-Kona

ORD - KOA

ORDKOA

Chicago O'Hare Intl

mié. 12/10

10:00 am-9:30 pm

1 stop15h 30m

Kona Intl

lun. 12/15

2:20 pm-2:09 pm

1 stop19h 49m

$447

ChicagoKailua-Kona

ORD - KOA

ORDKOA

Chicago O'Hare Intl

mié. 9/17

5:45 pm-11:16 am

1 stop22h 31m

Kona Intl

mié. 9/24

8:00 am-12:03 am

1 stop11h 03m

$447

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/24

Showing 1-10 of 56 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, October is the cheapest month in which you can book a flight from Chicago to The Big Island (average of $409). Flying from Chicago to The Big Island in June is currently the most expensive (average of $624). 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 agosto 25, 2025.

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 agosto 25, 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
10,000 reviews

Overall

8.0

Boarding

8.1

Crew

8.5

Entertainment

7.0

Food

7.1

Comfort

7.8

Reviews

1 / 20
10.0
Excellent

Anonymous,Aug 2025

PDX - SJC

They had no snacks and had to pay for the Wifi.
Alaska Airlines
8.0
Very good
10,000 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Overall

8.0

Boarding

8.1

Crew

8.5

Entertainment

7.0

Food

7.1

Comfort

7.8

Reviews

1 / 20
10.0
Excellent

Anonymous,Aug 2025

PDX - SJC

They had no snacks and had to pay for the Wifi.
Southwest
8.0
Very good
4,243 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Overall

8.0

Boarding

8.1

Crew

8.5

Entertainment

7.0

Food

7.1

Comfort

7.8

Reviews

1 / 20
10.0
Excellent

Anonymous,Aug 2025

PDX - SJC

They had no snacks and had to pay for the Wifi.
Delta
8.0
Very good
7,981 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Overall

8.0

Boarding

8.1

Crew

8.5

Entertainment

7.0

Food

7.1

Comfort

7.8

Reviews

1 / 20
10.0
Excellent

Anonymous,Aug 2025

PDX - SJC

They had no snacks and had to pay for the Wifi.
United Airlines
7.4
Good
8,940 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Overall

8.0

Boarding

8.1

Crew

8.5

Entertainment

7.0

Food

7.1

Comfort

7.8

Reviews

1 / 20
10.0
Excellent

Anonymous,Aug 2025

PDX - SJC

They had no snacks and had to pay for the Wifi.
American Airlines
7.2
Good
10,000 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Overall

8.0

Boarding

8.1

Crew

8.5

Entertainment

7.0

Food

7.1

Comfort

7.8

Reviews

1 / 20
10.0
Excellent

Anonymous,Aug 2025

PDX - SJC

They had no snacks and had to pay for the Wifi.

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 11h. 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?

    $224 is the cheapest one-way deal found within the past few days, from Delta. You may also be able to find cheap deals on Alaska Airlines and Southwest, with prices starting from $229 and $312, 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 - Hilo Intl, Chicago O'Hare Intl - Kona Intl and Chicago Midway - Kona 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, October is the cheapest month in which you can book a flight from Chicago to The Big Island (average of $409). Flying from Chicago to The Big Island in June is currently the most expensive (average of $624). 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.
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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 agosto 25, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$413Average$708FlexibilityNo cancel feeOn-time71%
DeltaCheapest$421Average$619FlexibilityNo cancel feeOn-timeN/A
Alaska AirlinesCheapest$429Average$769FlexibilityNo cancel feeOn-time75%
United AirlinesCheapest$490Average$895FlexibilityNo cancel feeOn-time69%
Hawaiian AirlinesCheapest$535Average$728FlexibilityNo cancel feeOn-time85%
SouthwestCheapest$593Average$724FlexibilityNo cancel feeOn-time63%

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