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The Big Island

$175+ 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 3/4. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — KOA
Feb 7 — Feb 141
Sat 2/7
Sat 2/14
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 January 8, 2026.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$310
(Delta)

One-way from

$175
(Delta)

Popular in

December

Cheapest in

September

Average price

$598
Provider with most accurate pricing for Chicago (CHI)-Kona Intl flight deals.
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Provider most trusted by Cheapflights users for Chicago (CHI)-Kona Intl flights.
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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. 6% potential increase in price ($46 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($31 potential savings vs. average RT price).
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Average for round-trip flights in January 2026
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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 January 8, 2026.

This Delta deal was found by Cheapflights users on 1/7. 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.
Tue 2/247:40 amORD - KOA
1 stop15h 59mDelta
Tue 3/108:55 pmKOA - ORD
1 stop11h 29mDelta
Deal found 1/7$310
This Delta deal was found by Cheapflights users on 1/8. 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.
Tue 2/246:30 amORD - KOA
2 stops17h 09mDelta
Mon 3/98:55 pmKOA - ORD
1 stop11h 29mDelta
Deal found 1/8$316
This Delta deal was found by Cheapflights users on 1/6. 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.
Wed 1/287:20 amORD - KOA
2 stops15h 27mDelta
Tue 2/109:55 pmKOA - ORD
1 stop11h 27mDelta
Deal found 1/6$336
This Alaska Airlines deal was found by Cheapflights users on 1/7. 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 3/57:00 amORD - KOA
1 stop19h 57mAlaska Airlines
Mon 3/910:57 pmKOA - ORD
2 stops19h 59mAlaska Airlines
Deal found 1/7$352
This American Airlines deal was found by Cheapflights users on 1/6. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 2/16:00 amORD - KOA
1 stop12h 54mAmerican Airlines
Fri 2/611:00 pmKOA - ORD
1 stop12h 57mAmerican Airlines
Deal found 1/6$358
This Expedia deal was found by Cheapflights users on 1/7. 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 2/248:20 amORD - KOA
2 stops17h 55mMultiple Airlines
Mon 3/910:57 pmKOA - ORD
2 stops19h 59mMultiple Airlines
Deal found 1/7$359
This Delta deal was found by Cheapflights users on 1/7. 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 1/297:30 amORD - KOA
2 stops15h 00mDelta
Thu 2/59:55 pmKOA - ORD
1 stop11h 27mDelta
Deal found 1/7$360
This Delta deal was found by Cheapflights users on 1/6. 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.
Wed 2/257:15 amORD - KOA
2 stops16h 24mDelta
Wed 3/49:55 pmKOA - ORD
2 stops15h 47mDelta
Deal found 1/6$361
This Expedia deal was found by Cheapflights users on 1/7. 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.
Sun 2/13:44 pmORD - KOA
1 stop28h 13mMultiple Airlines
Fri 2/62:21 pmKOA - ORD
2 stops20h 08mMultiple Airlines
Deal found 1/7$363
This American Airlines deal was found by Cheapflights users on 1/8. 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.
Tue 2/248:26 amORD - KOA
2 stops14h 33mAmerican Airlines
Tue 3/109:17 pmKOA - ORD
1 stop10h 14mAmerican Airlines
Deal found 1/8$364
This Southwest deal was found by Cheapflights users on 1/6. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/256:10 amMDW - KOA
1 stop11h 35mSouthwest
Wed 3/49:25 pmKOA - MDW
2 stops12h 50mSouthwest
Deal found 1/6$364
This Alaska Airlines deal was found by Cheapflights users on 1/6. 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.
Wed 2/49:00 amORD - ITO
2 stops16h 24mMultiple Airlines
Wed 2/118:30 pmITO - ORD
2 stops14h 28mMultiple Airlines
Deal found 1/6$371

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 8, 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

Tue 2/24

7:40 am-7:39 pm

1 stop15h 59m

Kona Intl

Tue 3/10

8:55 pm-6:06 pm

2 stops16h 11m

$316

ChicagoKailua-Kona

ORD - KOA

ORDKOA

Chicago O'Hare Intl

Thu 2/5

7:30 am-6:30 pm

2 stops15h 00m

Kona Intl

Thu 2/12

9:55 pm-1:22 pm

1 stop11h 27m

$360

ChicagoHilo

ORD - ITO

ORDITO

Chicago O'Hare Intl

Wed 2/4

9:00 am-9:24 pm

2 stops16h 24m

Hilo Intl

Wed 2/11

8:30 pm-2:58 pm

2 stops14h 28m

$371

ChicagoKailua-Kona

ORD - KOA

ORDKOA

Chicago O'Hare Intl

Fri 1/30

7:30 am-6:47 pm

1 stop15h 17m

Kona Intl

Fri 2/6

10:55 pm-4:38 pm

2 stops13h 43m

$373

ChicagoKailua-Kona

ORD - KOA

ORDKOA

Chicago O'Hare Intl

Thu 2/19

2:20 pm-6:30 pm

2 stops32h 10m

Kona Intl

Wed 2/25

9:55 pm-1:22 pm

1 stop11h 27m

$391

ChicagoKailua-Kona

ORD - KOA

ORDKOA

Chicago O'Hare Intl

Fri 2/20

7:40 am-6:30 pm

2 stops14h 50m

Kona Intl

Wed 2/25

9:55 pm-1:22 pm

1 stop11h 27m

$395

ChicagoKailua-Kona

ORD - KOA

ORDKOA

Chicago O'Hare Intl

Sun 2/8

2:06 pm-10:44 am

2 stops24h 38m

Kona Intl

Wed 2/11

10:50 am-2:58 pm

1 stop24h 08m

$396

ChicagoKailua-Kona

ORD - KOA

ORDKOA

Chicago O'Hare Intl

Thu 2/19

7:40 am-6:30 pm

2 stops14h 50m

Kona Intl

Tue 2/24

9:55 pm-1:22 pm

1 stop11h 27m

$400

ChicagoKailua-Kona

ORD - KOA

ORDKOA

Chicago O'Hare Intl

Wed 3/4

7:15 am-7:39 pm

2 stops16h 24m

Kona Intl

Thu 3/12

9:55 pm-9:34 pm

2 stops18h 39m

$400

ChicagoHilo

ORD - ITO

ORDITO

Chicago O'Hare Intl

Mon 1/26

9:00 am-9:24 pm

2 stops16h 24m

Hilo Intl

Mon 2/2

5:59 pm-2:38 pm

2 stops16h 39m

$408

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/8

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 $421). Flying from Chicago to The Big Island in July is currently the most expensive (average of $668). 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 8, 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 8, 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
11,661 reviews

Boarding

8.1

Crew

8.5

Food

7.1

Entertainment

7.0

Comfort

7.8

Overall

8.0

Reviews

1 / 20
4.0
Okay

Anonymous,Dec 2025

SEA - MSY

I really got a lesson in upgrades. I let my seat get chosen . Both times a middle seat...on purpose ...even when we were not full. That's petty I sat behind the first class . They got more than 1 drink ...and a snack . .and the staff actually talked to them...behind a see thru shawl/sheet in the aisle....... You could see over the seats just fine and you could hear the voices just fine. But the sheet let You KNOW. Your not welcome here. For a moment I regretted not spending 300 dollars per seat so I could see a smile and eat a sandwhich and enjoy my seat . The married couple drank champain and laughed and flirted with each other. It looked so happy and care free MONEY really does buy happiness ..the hateful glares and sighs from my seat mates brought me back to reality I wasn't rich and I still had 2 hours left in this middle seat.
Alaska Airlines
8.0
Very good
11,661 reviews
Alaska Airlines
8.0
Very good
11,661 reviews

Boarding

8.1

Crew

8.5

Food

7.1

Entertainment

7.0

Comfort

7.8

Overall

8.0

Reviews

1 / 20
4.0
Okay

Anonymous,Dec 2025

SEA - MSY

I really got a lesson in upgrades. I let my seat get chosen . Both times a middle seat...on purpose ...even when we were not full. That's petty I sat behind the first class . They got more than 1 drink ...and a snack . .and the staff actually talked to them...behind a see thru shawl/sheet in the aisle....... You could see over the seats just fine and you could hear the voices just fine. But the sheet let You KNOW. Your not welcome here. For a moment I regretted not spending 300 dollars per seat so I could see a smile and eat a sandwhich and enjoy my seat . The married couple drank champain and laughed and flirted with each other. It looked so happy and care free MONEY really does buy happiness ..the hateful glares and sighs from my seat mates brought me back to reality I wasn't rich and I still had 2 hours left in this middle seat.
Southwest
8.0
Very good
4,250 reviews
Alaska Airlines
8.0
Very good
11,661 reviews

Boarding

8.1

Crew

8.5

Food

7.1

Entertainment

7.0

Comfort

7.8

Overall

8.0

Reviews

1 / 20
4.0
Okay

Anonymous,Dec 2025

SEA - MSY

I really got a lesson in upgrades. I let my seat get chosen . Both times a middle seat...on purpose ...even when we were not full. That's petty I sat behind the first class . They got more than 1 drink ...and a snack . .and the staff actually talked to them...behind a see thru shawl/sheet in the aisle....... You could see over the seats just fine and you could hear the voices just fine. But the sheet let You KNOW. Your not welcome here. For a moment I regretted not spending 300 dollars per seat so I could see a smile and eat a sandwhich and enjoy my seat . The married couple drank champain and laughed and flirted with each other. It looked so happy and care free MONEY really does buy happiness ..the hateful glares and sighs from my seat mates brought me back to reality I wasn't rich and I still had 2 hours left in this middle seat.
Delta
7.9
Good
8,025 reviews
Alaska Airlines
8.0
Very good
11,661 reviews

Boarding

8.1

Crew

8.5

Food

7.1

Entertainment

7.0

Comfort

7.8

Overall

8.0

Reviews

1 / 20
4.0
Okay

Anonymous,Dec 2025

SEA - MSY

I really got a lesson in upgrades. I let my seat get chosen . Both times a middle seat...on purpose ...even when we were not full. That's petty I sat behind the first class . They got more than 1 drink ...and a snack . .and the staff actually talked to them...behind a see thru shawl/sheet in the aisle....... You could see over the seats just fine and you could hear the voices just fine. But the sheet let You KNOW. Your not welcome here. For a moment I regretted not spending 300 dollars per seat so I could see a smile and eat a sandwhich and enjoy my seat . The married couple drank champain and laughed and flirted with each other. It looked so happy and care free MONEY really does buy happiness ..the hateful glares and sighs from my seat mates brought me back to reality I wasn't rich and I still had 2 hours left in this middle seat.
United Airlines
7.4
Good
9,139 reviews
Alaska Airlines
8.0
Very good
11,661 reviews

Boarding

8.1

Crew

8.5

Food

7.1

Entertainment

7.0

Comfort

7.8

Overall

8.0

Reviews

1 / 20
4.0
Okay

Anonymous,Dec 2025

SEA - MSY

I really got a lesson in upgrades. I let my seat get chosen . Both times a middle seat...on purpose ...even when we were not full. That's petty I sat behind the first class . They got more than 1 drink ...and a snack . .and the staff actually talked to them...behind a see thru shawl/sheet in the aisle....... You could see over the seats just fine and you could hear the voices just fine. But the sheet let You KNOW. Your not welcome here. For a moment I regretted not spending 300 dollars per seat so I could see a smile and eat a sandwhich and enjoy my seat . The married couple drank champain and laughed and flirted with each other. It looked so happy and care free MONEY really does buy happiness ..the hateful glares and sighs from my seat mates brought me back to reality I wasn't rich and I still had 2 hours left in this middle seat.
American Airlines
7.2
Good
11,095 reviews
Alaska Airlines
8.0
Very good
11,661 reviews

Boarding

8.1

Crew

8.5

Food

7.1

Entertainment

7.0

Comfort

7.8

Overall

8.0

Reviews

1 / 20
4.0
Okay

Anonymous,Dec 2025

SEA - MSY

I really got a lesson in upgrades. I let my seat get chosen . Both times a middle seat...on purpose ...even when we were not full. That's petty I sat behind the first class . They got more than 1 drink ...and a snack . .and the staff actually talked to them...behind a see thru shawl/sheet in the aisle....... You could see over the seats just fine and you could hear the voices just fine. But the sheet let You KNOW. Your not welcome here. For a moment I regretted not spending 300 dollars per seat so I could see a smile and eat a sandwhich and enjoy my seat . The married couple drank champain and laughed and flirted with each other. It looked so happy and care free MONEY really does buy happiness ..the hateful glares and sighs from my seat mates brought me back to reality I wasn't rich and I still had 2 hours left in this middle seat.

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 35m. 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 $421). Flying from Chicago to The Big Island in July is currently the most expensive (average of $668). 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 January 8, 2026.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$371Average$619FlexibilityNo cancel feeOn-timeN/A
Alaska AirlinesCheapest$424Average$774FlexibilityNo cancel feeOn-time75%
Hawaiian AirlinesCheapest$429Average$651FlexibilityNo cancel feeOn-time85%
United AirlinesCheapest$447Average$1,110FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$452Average$715FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$593Average$722FlexibilityNo cancel feeOn-time63%

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