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The Big Island

$187+ 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 12/9. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — KOA
Dec 6 — Dec 131
Sat 12/6
Sat 12/13
1 adult, Economy
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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 November 6, 2025.

This Alaska Airlines deal was found by Cheapflights users on 11/6. 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 12/43:05 pmORD - KOA
2 stops25h 50mAlaska Airlines
Thu 12/112:20 pmKOA - ORD
1 stop19h 49mAlaska Airlines
Deal found 11/6$399
This Alaska Airlines deal was found by Cheapflights users on 11/5. 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.
Sat 12/63:05 pmORD - KOA
1 stop28h 55mAlaska Airlines
Wed 12/102:20 pmKOA - ORD
1 stop29h 30mAlaska Airlines
Deal found 11/5$403
This Kiwi.com deal was found by Cheapflights users on 11/5. 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.
Mon 12/88:55 amORD - KOA
1 stop11h 05mAlaska Airlines
Fri 12/126:00 amKOA - ORD
2 stops13h 50mAlaska Airlines
Deal found 11/5$417
This Orbitz deal was found by Cheapflights users on 11/5. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/73:05 pmORD - KOA
1 stop28h 55mAlaska Airlines
Sat 12/131:45 pmKOA - ORD
2 stops20h 24mAlaska Airlines
Deal found 11/5$420
This Alaska Airlines deal was found by Cheapflights users on 11/5. 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 12/118:55 amORD - KOA
1 stop11h 05mAlaska Airlines
Thu 12/182:25 pmKOA - ORD
1 stop25h 37mAlaska Airlines
Deal found 11/5$425
This Alaska Airlines deal was found by Cheapflights users on 11/4. 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.
Fri 12/58:55 amORD - ITO
2 stops17h 41mAlaska Airlines
Thu 12/117:44 pmITO - ORD
2 stops24h 06mAlaska Airlines
Deal found 11/4$426
This Alaska Airlines deal was found by Cheapflights users on 11/5. 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.
Sat 12/63:05 pmORD - KOA
1 stop28h 55mAlaska Airlines
Sat 12/132:20 pmKOA - ORD
1 stop29h 30mAlaska Airlines
Deal found 11/5$433
This Delta deal was found by Cheapflights users on 11/6. 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 12/49:34 amMDW - KOA
2 stops13h 56mDelta
Thu 12/118:43 pmKOA - MDW
2 stops15h 35mDelta
Deal found 11/6$434
This Alaska Airlines deal was found by Cheapflights users on 11/6. 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 12/48:55 amORD - ITO
2 stops33h 37mAlaska Airlines
Mon 12/88:30 pmITO - ORD
2 stops23h 20mAlaska Airlines
Deal found 11/6$455
This Alaska Airlines deal was found by Cheapflights users on 11/6. 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 12/43:05 pmORD - ITO
2 stops27h 27mAlaska Airlines
Thu 12/116:44 pmITO - ORD
2 stops15h 25mAlaska Airlines
Deal found 11/6$474
This Delta deal was found by Cheapflights users on 11/5. 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 12/69:59 amMDW - KOA
2 stops13h 31mDelta
Wed 12/108:43 pmKOA - MDW
2 stops15h 35mDelta
Deal found 11/5$514
This Delta deal was found by Cheapflights users on 11/5. 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 12/56:00 amMDW - KOA
2 stops16h 21mDelta
Fri 12/128:43 pmKOA - MDW
2 stops17h 23mDelta
Deal found 11/5$530

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 November 6, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$375
(Alaska Airlines)

One-way from

$187
(Alaska Airlines)

Popular in

December

Cheapest in

September

Average price

$888

Good round-trip deal

$1,163 or less

Good one-way deal

$582 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. 11% potential increase in price ($91 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($24 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in November 2025
Search Deals
Price to beat on a round-trip flight from Chicago (CHI) to The Big Island.
Search Deals
Price to beat on a one-way 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 November 6, 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

Sun 2/1

9:00 am-3:57 pm

1 stop34h 57m

Kona Intl

Wed 2/11

2:51 pm-11:10 pm

1 stop28h 19m

$383

ChicagoHilo

ORD - ITO

ORDITO

Chicago O'Hare Intl

Sun 1/25

3:49 pm-5:29 pm

2 stops29h 40m

Hilo Intl

Fri 1/30

6:00 am-2:29 pm

2 stops28h 29m

$414

ChicagoKailua-Kona

ORD - KOA

ORDKOA

Chicago O'Hare Intl

Mon 12/8

3:05 pm-4:00 pm

1 stop28h 55m

Kona Intl

Fri 12/12

2:20 pm-11:50 pm

1 stop29h 30m

$423

ChicagoHilo

ORD - ITO

ORDITO

Chicago O'Hare Intl

Thu 1/22

9:00 am-9:24 pm

2 stops16h 24m

Hilo Intl

Thu 1/29

8:59 am-2:29 pm

2 stops25h 30m

$425

ChicagoKailua-Kona

ORD - KOA

ORDKOA

Chicago O'Hare Intl

Thu 1/15

9:00 am-8:28 pm

2 stops15h 28m

Kona Intl

Thu 1/22

6:00 am-11:37 pm

2 stops13h 37m

$425

ChicagoHilo

ORD - ITO

ORDITO

Chicago O'Hare Intl

Fri 12/5

8:55 am-10:36 pm

2 stops17h 41m

Hilo Intl

Thu 12/11

7:44 pm-11:50 pm

2 stops24h 06m

$426

ChicagoKailua-Kona

ORD - KOA

ORDKOA

Chicago O'Hare Intl

Fri 12/5

8:55 am-4:00 pm

1 stop11h 05m

Kona Intl

Fri 12/12

6:00 am-11:50 pm

2 stops13h 50m

$451

ChicagoKailua-Kona

MDW - KOA

MDWKOA

Chicago Midway

Wed 1/28

6:00 am-6:47 pm

2 stops16h 47m

Kona Intl

Wed 2/4

8:45 pm-5:32 pm

2 stops16h 47m

$454

ChicagoKailua-Kona

MDW - KOA

MDWKOA

Chicago Midway

Wed 2/25

9:34 am-7:34 pm

2 stops14h 00m

Kona Intl

Tue 3/3

9:45 pm-5:37 pm

2 stops15h 52m

$455

ChicagoHilo

ORD - ITO

ORDITO

Chicago O'Hare Intl

Thu 12/4

8:55 am-2:32 pm

2 stops33h 37m

Hilo Intl

Mon 12/8

8:30 pm-11:50 pm

2 stops23h 20m

$455

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/5

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, January is the cheapest month in which you can book a flight from Chicago to The Big Island (average of $420). Flying from Chicago to The Big Island in July is currently the most expensive (average of $667). 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 November 6, 2025.

When flying from Chicago to The Big Island, the time of day you fly usually plays a role in the price. Save by searching for a flight at noon, which can drop the price by up to 31% versus a flight in the evening.

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 November 6, 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
11,247 reviews

Food

7.1

Comfort

7.8

Crew

8.5

Entertainment

7.0

Overall

8.0

Boarding

8.1

Reviews

1 / 20
10.0
Excellent

Anonymous,Sep 2025

BOS - HNL

The flight was awesome but a little long. I would prefer a flight with a layover. The amount of space available was minimal and a little uncomfortable for that long of a flight.
Alaska Airlines
8.0
Very good
11,247 reviews
Alaska Airlines
8.0
Very good
11,247 reviews

Food

7.1

Comfort

7.8

Crew

8.5

Entertainment

7.0

Overall

8.0

Boarding

8.1

Reviews

1 / 20
10.0
Excellent

Anonymous,Sep 2025

BOS - HNL

The flight was awesome but a little long. I would prefer a flight with a layover. The amount of space available was minimal and a little uncomfortable for that long of a flight.
Southwest
8.0
Very good
4,241 reviews
Alaska Airlines
8.0
Very good
11,247 reviews

Food

7.1

Comfort

7.8

Crew

8.5

Entertainment

7.0

Overall

8.0

Boarding

8.1

Reviews

1 / 20
10.0
Excellent

Anonymous,Sep 2025

BOS - HNL

The flight was awesome but a little long. I would prefer a flight with a layover. The amount of space available was minimal and a little uncomfortable for that long of a flight.
Delta
7.9
Good
8,001 reviews
Alaska Airlines
8.0
Very good
11,247 reviews

Food

7.1

Comfort

7.8

Crew

8.5

Entertainment

7.0

Overall

8.0

Boarding

8.1

Reviews

1 / 20
10.0
Excellent

Anonymous,Sep 2025

BOS - HNL

The flight was awesome but a little long. I would prefer a flight with a layover. The amount of space available was minimal and a little uncomfortable for that long of a flight.
United Airlines
7.4
Good
9,007 reviews
Alaska Airlines
8.0
Very good
11,247 reviews

Food

7.1

Comfort

7.8

Crew

8.5

Entertainment

7.0

Overall

8.0

Boarding

8.1

Reviews

1 / 20
10.0
Excellent

Anonymous,Sep 2025

BOS - HNL

The flight was awesome but a little long. I would prefer a flight with a layover. The amount of space available was minimal and a little uncomfortable for that long of a flight.
American Airlines
7.2
Good
11,040 reviews
Alaska Airlines
8.0
Very good
11,247 reviews

Food

7.1

Comfort

7.8

Crew

8.5

Entertainment

7.0

Overall

8.0

Boarding

8.1

Reviews

1 / 20
10.0
Excellent

Anonymous,Sep 2025

BOS - HNL

The flight was awesome but a little long. I would prefer a flight with a layover. The amount of space available was minimal and a little uncomfortable for that long of a flight.

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 47m. 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?

    $187 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 Delta and Southwest, with prices starting from $227 and $290, 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.

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

    While on average a flight from Chicago to The Big Island is generally $873, our data shows the cheapest flight currently is $582. When looking at the most popular route, (Chicago O'Hare Intl - Kona Intl), you can expect to pay $404 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, January is the cheapest month in which you can book a flight from Chicago to The Big Island (average of $420). Flying from Chicago to The Big Island in July is currently the most expensive (average of $667). 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 November 6, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$371Average$668FlexibilityNo cancel feeOn-timeN/A
Hawaiian AirlinesCheapest$429Average$651FlexibilityNo cancel feeOn-time85%
Alaska AirlinesCheapest$441Average$705FlexibilityNo cancel feeOn-time75%
United AirlinesCheapest$447Average$1,005FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$466Average$731FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$593Average$742FlexibilityNo cancel feeOn-time63%

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