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The Big Island

$222+ 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 10/30. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — KOA
Oct 11 — Oct 181
Sat 10/11
Sat 10/18
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 September 11, 2025.

Round-trip from

$431
(Delta)

One-way from

$222
(Delta)

Popular in

March

Cheapest in

September

Average price

$539
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. 3% potential increase in price ($21 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 September 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 September 11, 2025.

This Delta deal was found by Cheapflights users on 9/11. 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 10/227:37 amORD - KOA
2 stops16h 46mDelta
Mon 10/279:30 pmKOA - ORD
1 stop14h 40mDelta
Deal found 9/11$431
This Delta deal was found by Cheapflights users on 9/11. 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 10/227:37 amORD - KOA
2 stops16h 46mDelta
Tue 11/49:30 pmKOA - ORD
2 stops15h 40mDelta
Deal found 9/11$436
This Delta deal was found by Cheapflights users on 9/11. 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.
Sat 11/15:15 pmORD - KOA
2 stops31h 38mDelta
Mon 11/108:30 pmKOA - ORD
1 stop23h 28mDelta
Deal found 9/11$437
This Alaska Airlines deal was found by Cheapflights users on 9/11. 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.
Tue 11/48:00 amORD - ITO
2 stops18h 22mAlaska Airlines
Mon 11/177:43 pmITO - ORD
2 stops24h 41mAlaska Airlines
Deal found 9/11$440
This Delta deal was found by Cheapflights users on 9/11. 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 10/27:10 amORD - KOA
2 stops15h 25mDelta
Mon 10/69:30 pmKOA - ORD
1 stop11h 00mDelta
Deal found 9/11$440
This Delta deal was found by Cheapflights users on 9/11. 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 10/317:37 amORD - KOA
1 stop14h 53mDelta
Mon 11/108:30 pmKOA - ORD
1 stop13h 04mDelta
Deal found 9/11$441
This Alaska Airlines deal was found by Cheapflights users on 9/9. 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 10/207:59 pmORD - KOA
1 stop21h 30mAlaska Airlines
Tue 10/289:20 pmKOA - ORD
1 stop22h 04mAlaska Airlines
Deal found 9/9$444
This Delta deal was found by Cheapflights users on 9/11. 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 10/27:10 amORD - KOA
2 stops15h 25mDelta
Tue 10/78:30 pmKOA - ORD
2 stops15h 40mDelta
Deal found 9/11$445
This Alaska Airlines deal was found by Cheapflights users on 9/11. 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.
Thu 10/238:00 amORD - ITO
2 stops17h 31mAlaska Airlines
Mon 10/279:00 pmITO - ORD
2 stops22h 24mAlaska Airlines
Deal found 9/11$449
This Delta deal was found by Cheapflights users on 9/11. 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 10/307:37 amORD - KOA
1 stop14h 53mDelta
Fri 11/79:30 pmKOA - ORD
1 stop15h 48mDelta
Deal found 9/11$450
This Alaska Airlines deal was found by Cheapflights users on 9/11. 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 10/277:59 pmORD - KOA
1 stop22h 44mAlaska Airlines
Fri 10/3111:09 amKOA - ORD
1 stop21h 45mAlaska Airlines
Deal found 9/11$451
This American Airlines deal was found by Cheapflights users on 9/10. 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.
Thu 10/236:03 amORD - KOA
1 stop12h 55mAmerican Airlines
Sun 11/24:32 pmKOA - ORD
1 stop10h 11mAmerican Airlines
Deal found 9/10$452

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 September 11, 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

Wed 10/22

7:37 am-7:23 pm

2 stops16h 46m

Kona Intl

Tue 11/4

9:30 pm-5:10 pm

1 stop15h 40m

$431

ChicagoKailua-Kona

ORD - KOA

ORDKOA

Chicago O'Hare Intl

Sat 11/1

5:15 pm-7:53 pm

2 stops31h 38m

Kona Intl

Mon 11/10

8:30 pm-11:58 pm

1 stop23h 28m

$437

ChicagoHilo

ORD - ITO

ORDITO

Chicago O'Hare Intl

Tue 11/4

8:00 am-10:22 pm

2 stops18h 22m

Hilo Intl

Mon 11/17

7:43 pm-12:24 am

2 stops24h 41m

$440

ChicagoKailua-Kona

ORD - KOA

ORDKOA

Chicago O'Hare Intl

Thu 10/2

7:10 am-5:35 pm

2 stops15h 25m

Kona Intl

Tue 10/7

9:30 pm-1:30 pm

1 stop11h 00m

$440

ChicagoKailua-Kona

ORD - KOA

ORDKOA

Chicago O'Hare Intl

Wed 10/8

7:37 am-7:23 pm

2 stops16h 46m

Kona Intl

Wed 10/22

9:30 pm-1:30 pm

1 stop11h 00m

$447

ChicagoHilo

ORD - ITO

ORDITO

Chicago O'Hare Intl

Thu 10/23

8:00 am-8:31 pm

2 stops17h 31m

Hilo Intl

Mon 10/27

9:00 pm-12:24 am

2 stops22h 24m

$449

ChicagoHilo

ORD - ITO

ORDITO

Chicago O'Hare Intl

Mon 11/3

6:00 am-10:22 pm

2 stops20h 22m

Hilo Intl

Mon 11/10

9:00 pm-12:24 am

2 stops23h 24m

$449

ChicagoKailua-Kona

ORD - KOA

ORDKOA

Chicago O'Hare Intl

Thu 10/30

7:37 am-5:30 pm

1 stop14h 53m

Kona Intl

Fri 11/7

9:30 pm-5:18 pm

1 stop15h 48m

$450

ChicagoKailua-Kona

ORD - KOA

ORDKOA

Chicago O'Hare Intl

Mon 10/27

7:59 pm-1:43 pm

1 stop22h 44m

Kona Intl

Fri 10/31

11:09 am-1:54 pm

1 stop21h 45m

$451

ChicagoKailua-Kona

ORD - KOA

ORDKOA

Chicago O'Hare Intl

Sun 11/16

7:47 am-6:13 pm

1 stop14h 26m

Kona Intl

Wed 11/26

8:53 pm-1:34 pm

1 stop12h 41m

$452

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/11

Showing 1-10 of 49 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 September 11, 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 September 11, 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

Boarding

8.1

Entertainment

7.0

Comfort

7.8

Food

7.1

Crew

8.5

Overall

8.0

Reviews

1 / 20
6.0
Good

Hannah,Aug 2025

SFO - SAN

Ticket said TSA pre check, but then the TSA agent said that Alaska Airlines has not actually entered the pre check information for the ticket, so I had to use regular security. During boarding, I have a disability and need to board early. The Alaska Airlines employee announced disability boarding, but then immediately announced 2 other groups to board, so I still had to fight the crowds. On the plane, the stewardess was brusk and rude. Seats were very uncomfortable, especially on lower back.
Alaska Airlines
8.0
Very good
10,000 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Boarding

8.1

Entertainment

7.0

Comfort

7.8

Food

7.1

Crew

8.5

Overall

8.0

Reviews

1 / 20
6.0
Good

Hannah,Aug 2025

SFO - SAN

Ticket said TSA pre check, but then the TSA agent said that Alaska Airlines has not actually entered the pre check information for the ticket, so I had to use regular security. During boarding, I have a disability and need to board early. The Alaska Airlines employee announced disability boarding, but then immediately announced 2 other groups to board, so I still had to fight the crowds. On the plane, the stewardess was brusk and rude. Seats were very uncomfortable, especially on lower back.
Southwest
8.0
Very good
4,248 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Boarding

8.1

Entertainment

7.0

Comfort

7.8

Food

7.1

Crew

8.5

Overall

8.0

Reviews

1 / 20
6.0
Good

Hannah,Aug 2025

SFO - SAN

Ticket said TSA pre check, but then the TSA agent said that Alaska Airlines has not actually entered the pre check information for the ticket, so I had to use regular security. During boarding, I have a disability and need to board early. The Alaska Airlines employee announced disability boarding, but then immediately announced 2 other groups to board, so I still had to fight the crowds. On the plane, the stewardess was brusk and rude. Seats were very uncomfortable, especially on lower back.
Delta
8.0
Very good
7,960 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Boarding

8.1

Entertainment

7.0

Comfort

7.8

Food

7.1

Crew

8.5

Overall

8.0

Reviews

1 / 20
6.0
Good

Hannah,Aug 2025

SFO - SAN

Ticket said TSA pre check, but then the TSA agent said that Alaska Airlines has not actually entered the pre check information for the ticket, so I had to use regular security. During boarding, I have a disability and need to board early. The Alaska Airlines employee announced disability boarding, but then immediately announced 2 other groups to board, so I still had to fight the crowds. On the plane, the stewardess was brusk and rude. Seats were very uncomfortable, especially on lower back.
United Airlines
7.4
Good
8,937 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Boarding

8.1

Entertainment

7.0

Comfort

7.8

Food

7.1

Crew

8.5

Overall

8.0

Reviews

1 / 20
6.0
Good

Hannah,Aug 2025

SFO - SAN

Ticket said TSA pre check, but then the TSA agent said that Alaska Airlines has not actually entered the pre check information for the ticket, so I had to use regular security. During boarding, I have a disability and need to board early. The Alaska Airlines employee announced disability boarding, but then immediately announced 2 other groups to board, so I still had to fight the crowds. On the plane, the stewardess was brusk and rude. Seats were very uncomfortable, especially on lower back.
American Airlines
7.2
Good
10,000 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Boarding

8.1

Entertainment

7.0

Comfort

7.8

Food

7.1

Crew

8.5

Overall

8.0

Reviews

1 / 20
6.0
Good

Hannah,Aug 2025

SFO - SAN

Ticket said TSA pre check, but then the TSA agent said that Alaska Airlines has not actually entered the pre check information for the ticket, so I had to use regular security. During boarding, I have a disability and need to board early. The Alaska Airlines employee announced disability boarding, but then immediately announced 2 other groups to board, so I still had to fight the crowds. On the plane, the stewardess was brusk and rude. Seats were very uncomfortable, especially on lower back.

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 46m. 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?

    $222 is the cheapest one-way deal found within the past few days, from Delta. You may also be able to find cheap deals on American Airlines and Southwest, with prices starting from $224 and $224, 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 O'Hare Intl - Hilo 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.
O'Hare Intl to Honolulu flights
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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 September 11, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$421Average$656FlexibilityNo cancel feeOn-timeN/A
Alaska AirlinesCheapest$423Average$797FlexibilityNo cancel feeOn-time75%
American AirlinesCheapest$426Average$726FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$472Average$893FlexibilityNo cancel feeOn-time69%
Hawaiian AirlinesCheapest$535Average$681FlexibilityNo cancel feeOn-time85%
SouthwestCheapest$593Average$724FlexibilityNo cancel feeOn-time63%

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