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The Big Island

$280+ 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 6/3. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — KOA
May 6 — May 131
Tue 5/6
Tue 5/13
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 May 1, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$545
(American Airlines)

One-way from

$280
(Alaska Airlines)

Popular in

December

Cheapest in

September

Average price

$678
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. 2% potential increase in price ($15 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($24 potential savings vs. average RT price).
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Average for round-trip flights in May 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 May 1, 2025.

This American Airlines deal was found by Cheapflights users on 4/30. 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 9/305:00 amORD - KOA
1 stop13h 42mAmerican Airlines
Wed 12/1710:27 pmKOA - ORD
1 stop11h 44mAmerican Airlines
Deal found 4/30$545
This Delta deal was found by Cheapflights users on 4/30. 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 9/306:00 amORD - KOA
2 stops16h 44mDelta
Wed 12/1710:45 pmKOA - ORD
1 stop10h 43mDelta
Deal found 4/30$550
This Delta deal was found by Cheapflights users on 4/30. 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.
Sun 9/219:20 amMDW - KOA
2 stops14h 20mDelta
Tue 9/308:40 pmKOA - MDW
2 stops16h 27mDelta
Deal found 4/30$566
This Alaska Airlines deal was found by Cheapflights users on 4/30. 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 6/310:00 amORD - KOA
1 stop17h 15mAlaska Airlines
Mon 6/98:00 amKOA - ORD
1 stop10h 59mAlaska Airlines
Deal found 4/30$571
This Southwest deal was found by Cheapflights users on 4/30. 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.
Tue 5/209:25 pmMDW - KOA
2 stops19h 45mSouthwest
Wed 5/288:30 pmKOA - MDW
1 stop10h 15mSouthwest
Deal found 4/30$664
This Alaska Airlines deal was found by Cheapflights users on 4/30. 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 9/126:20 amORD - ITO
2 stops13h 58mAlaska Airlines
Tue 9/167:49 amITO - ORD
2 stops18h 14mAlaska Airlines
Deal found 4/30$710
This Southwest deal was found by Cheapflights users on 4/30. 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 5/286:15 amORD - ITO
2 stops16h 55mSouthwest
Wed 6/46:00 amITO - ORD
2 stops12h 40mSouthwest
Deal found 4/30$724
This United Airlines deal was found by Cheapflights users on 4/30. 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.
Mon 7/77:10 amORD - KOA
1 stop13h 09mUnited Airlines
Fri 7/181:10 pmKOA - ORD
1 stop11h 29mUnited Airlines
Deal found 4/30$792
This United Airlines deal was found by Cheapflights users on 4/30. 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.
Mon 9/19:30 amORD - ITO
1 stop27h 37mUnited Airlines
Sun 9/77:49 amITO - ORD
1 stop17h 34mUnited Airlines
Deal found 4/30$796
This Delta deal was found by Cheapflights users on 4/30. 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 6/46:20 pmORD - ITO
2 stops27h 41mDelta
Thu 6/125:25 pmITO - ORD
2 stops18h 55mDelta
Deal found 4/30$931
This Travelocity deal was found by Cheapflights users on 4/30. 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 Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/26:00 amORD - MUE
2 stops18h 13mMultiple Airlines
Sat 8/97:17 amMUE - ORD
2 stops17h 23mMultiple Airlines
Deal found 4/30$999
This Delta deal was found by Cheapflights users on 4/30. 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 6/106:00 amMDW - ITO
2 stops18h 09mDelta
Tue 6/1710:44 amITO - MDW
2 stops17h 57mDelta
Deal found 4/30$1,176

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 May 1, 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 6/4

6:20 pm-5:31 pm

1 stop28h 11m

Kona Intl

Mon 6/16

9:40 pm-12:03 am

1 stop21h 23m

$558

ChicagoKailua-Kona

ORD - KOA

ORDKOA

Chicago O'Hare Intl

Tue 6/3

10:00 am-10:15 pm

1 stop17h 15m

Kona Intl

Mon 6/9

8:00 am-11:59 pm

1 stop10h 59m

$571

ChicagoKailua-Kona

MDW - KOA

MDWKOA

Chicago Midway

Mon 6/2

9:20 am-7:10 pm

2 stops14h 50m

Kona Intl

Tue 6/10

8:35 pm-6:41 pm

2 stops17h 06m

$592

ChicagoKailua-Kona

ORD - KOA

ORDKOA

Chicago O'Hare Intl

Tue 5/13

7:06 am-2:37 pm

1 stop12h 31m

Kona Intl

Wed 5/21

1:47 pm-5:53 am

1 stop11h 06m

$602

ChicagoKailua-Kona

MDW - KOA

MDWKOA

Chicago Midway

Tue 5/20

9:25 pm-12:10 pm

2 stops19h 45m

Kona Intl

Wed 5/28

8:30 pm-11:45 am

1 stop10h 15m

$664

ChicagoHilo

ORD - ITO

ORDITO

Chicago O'Hare Intl

Wed 5/28

6:15 am-6:10 pm

2 stops16h 55m

Hilo Intl

Wed 6/4

6:00 am-11:40 pm

2 stops12h 40m

$724

ChicagoKailua-Kona

ORD - KOA

ORDKOA

Chicago O'Hare Intl

Mon 7/7

7:10 am-3:19 pm

1 stop13h 09m

Kona Intl

Fri 7/18

1:10 pm-5:39 am

1 stop11h 29m

$792

ChicagoKailua-Kona

ORD - KOA

ORDKOA

Chicago O'Hare Intl

Wed 7/2

6:15 am-5:55 pm

2 stops16h 40m

Kona Intl

Thu 7/10

6:00 am-11:40 pm

2 stops12h 40m

$834

ChicagoHilo

ORD - ITO

ORDITO

Chicago O'Hare Intl

Tue 6/10

6:00 am-5:57 pm

2 stops16h 57m

Hilo Intl

Tue 6/17

5:25 pm-11:59 pm

2 stops25h 34m

$872

ChicagoHilo

ORD - ITO

ORDITO

Chicago O'Hare Intl

Tue 6/10

4:48 pm-5:57 pm

2 stops30h 09m

Hilo Intl

Tue 6/17

8:36 am-11:04 pm

2 stops33h 28m

$906

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/30

Showing 1-10 of 24 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 May 1, 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.

Rainfall in The Big Island by month

Plan your trip to The Big Island by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in The Big Island ranges from 1.6 - 2.8 inches per month. January is typically the wettest month, when rainfall can reach 2.8 in. February is typically the driest time to visit The Big Island when rainfall is around 1.6 in.

Temperature in The Big Island by month

Plan your trip to The Big Island by taking into account the average temperature totals by month.

If weather is an important factor for your trip to The Big Island, use this chart to help with planning. For those seeking warmer temperatures, August is the ideal time of year to visit, when temperatures reach an average of 77.0 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 71.6 F).

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 May 1, 2025.
Peruse reviews from past customers who have flown with Alaska Airlines, Southwest and Delta from Chicago to The Big Island to help guide your decision. 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
9,968 reviews

Overall

8.0

Entertainment

7.1

Crew

8.5

Boarding

8.2

Food

7.1

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Alaska Airlines
8.0
Very good
9,968 reviews
Alaska Airlines
8.0
Very good
9,968 reviews

Overall

8.0

Entertainment

7.1

Crew

8.5

Boarding

8.2

Food

7.1

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Southwest
8.0
Very good
4,294 reviews
Alaska Airlines
8.0
Very good
9,968 reviews

Overall

8.0

Entertainment

7.1

Crew

8.5

Boarding

8.2

Food

7.1

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Delta
8.0
Very good
7,934 reviews
Alaska Airlines
8.0
Very good
9,968 reviews

Overall

8.0

Entertainment

7.1

Crew

8.5

Boarding

8.2

Food

7.1

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Hawaiian Airlines
7.9
Good
2,409 reviews
Alaska Airlines
8.0
Very good
9,968 reviews

Overall

8.0

Entertainment

7.1

Crew

8.5

Boarding

8.2

Food

7.1

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
United Airlines
7.4
Good
8,696 reviews
Alaska Airlines
8.0
Very good
9,968 reviews

Overall

8.0

Entertainment

7.1

Crew

8.5

Boarding

8.2

Food

7.1

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.

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.

  • What are the cheapest airlines to fly from Chicago to The Big Island one-way?

    $280 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 Delta, with prices starting from $291 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 - 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, 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
O'Hare Intl to Kahului flights
Midway to Honolulu flights
O'Hare Intl to Kailua-Kona flights
St. Louis to Honolulu flights
O'Hare Intl to Lihue flights
Midway to Kahului flights
St. Louis to Kahului flights
Midway to Kailua-Kona flights
Midway to Lihue flights
St. Louis to Lihue flights
O'Hare Intl to Hilo flights
St. Louis to Kailua-Kona flights
Bloomington to Kahului flights
Peoria to Honolulu flights
St. Louis to Hilo flights
Peoria to Kahului flights
Moline to Honolulu flights
Bloomington to Honolulu flights
Midway to Hilo flights
St. Louis to Kapalua flights
Evansville to Honolulu flights
Springfield to Honolulu flights
O'Hare Intl to Waimea (Big Island) flights
Moline to Kahului flights
O'Hare Intl to Kapalua flights
Moline to Lihue flights
Peoria to Lihue flights
Evansville to Lihue flights
St. Louis to Waimea (Big Island) flights
O'Hare Intl to Hana flights
Evansville to Kahului flights
Dubuque to Honolulu flights
St. Louis to Hana flights
Decatur to Honolulu flights
Springfield to Kahului flights
Springfield to Lihue flights
Moline to Hilo flights
Bloomington to Lihue flights
Champaign to Honolulu flights
Moline to Kailua-Kona 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 May 1, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$318Average$568FlexibilityNo cancel feeOn-timeN/A
Alaska AirlinesCheapest$409Average$647FlexibilityNo cancel feeOn-time75%
American AirlinesCheapest$412Average$689FlexibilityNo cancel feeOn-time71%
Hawaiian AirlinesCheapest$445Average$733FlexibilityNo cancel feeOn-time85%
United AirlinesCheapest$509Average$847FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$593Average$718FlexibilityNo cancel feeOn-time63%

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