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The Big Island

$233+ 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 9/20. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — KOA
Jun 21 — Jun 281
Sat 6/21
Sat 6/28
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 June 16, 2025.

Round-trip from

$466
(Alaska Airlines)

One-way from

$233
(American Airlines)

Popular in

March

Cheapest in

September

Average price

$822
From Chicago (CHI) to The Big Island
Search Deals
One-way flight from Chicago (CHI) to The Big Island
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Highest demand for flights based on searches. 3% potential increase in price ($25 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 June 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 June 16, 2025.

This Alaska Airlines deal was found by Cheapflights users on 6/15. 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 9/2410:00 amORD - ITO
2 stops36h 39mAlaska Airlines
Tue 9/307:00 pmITO - ORD
2 stops23h 59mAlaska Airlines
Deal found 6/15$408
This Delta deal was found by Cheapflights users on 6/16. 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 9/177:30 amORD - KOA
1 stop15h 14mDelta
Wed 9/249:45 pmKOA - ORD
1 stop10h 43mDelta
Deal found 6/16$465
This Alaska Airlines deal was found by Cheapflights users on 6/16. 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 9/171:01 pmORD - KOA
2 stops14h 12mAlaska Airlines
Wed 9/248:00 amKOA - ORD
1 stop10h 59mAlaska Airlines
Deal found 6/16$469
This American Airlines deal was found by Cheapflights users on 6/15. 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.
Fri 8/18:51 pmORD - KOA
1 stop22h 36mAmerican Airlines
Fri 9/59:55 pmKOA - ORD
1 stop13h 03mAmerican Airlines
Deal found 6/15$630
This Trip.com deal was found by Cheapflights users on 6/14. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/163:18 pmORD - KOA
2 stops20h 59mMultiple Airlines
Thu 7/316:00 amKOA - ORD
2 stops27h 13mMultiple Airlines
Deal found 6/14$645
This Delta deal was found by Cheapflights users on 6/13. 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 8/126:04 amMDW - KOA
2 stops17h 56mDelta
Mon 8/188:41 pmKOA - MDW
2 stops15h 56mDelta
Deal found 6/13$659
This Trip.com deal was found by Cheapflights users on 6/14. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/116:00 amORD - KOA
1 stop14h 19mHawaiian Airlines
Mon 7/148:00 amKOA - ORD
1 stop10h 59mHawaiian Airlines
Deal found 6/14$705
This Southwest deal was found by Cheapflights users on 6/15. 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.
Fri 8/15:30 amMDW - KOA
2 stops17h 25mSouthwest
Fri 9/59:15 amKOA - MDW
2 stops14h 55mSouthwest
Deal found 6/15$715
This Trip.com deal was found by Cheapflights users on 6/15. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/143:18 pmORD - ITO
2 stops21h 50mMultiple Airlines
Sun 7/206:00 amITO - ORD
2 stops19h 03mMultiple Airlines
Deal found 6/15$722
This United Airlines deal was found by Cheapflights users on 6/14. 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 7/147:49 pmORD - KOA
2 stops20h 42mUnited Airlines
Mon 7/2110:15 pmKOA - ORD
2 stops19h 51mUnited Airlines
Deal found 6/14$752
This Southwest deal was found by Cheapflights users on 6/15. 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.
Fri 8/17:15 amMDW - ITO
2 stops13h 45mSouthwest
Fri 9/56:55 pmITO - MDW
2 stops16h 50mSouthwest
Deal found 6/15$769
This Southwest deal was found by Cheapflights users on 6/15. 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.
Thu 6/266:15 amORD - ITO
2 stops16h 55mSouthwest
Wed 7/26:00 amITO - ORD
2 stops12h 40mSouthwest
Deal found 6/15$804

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 June 16, 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

Mon 9/1

6:20 am-5:39 pm

2 stops16h 19m

Hilo Intl

Fri 9/5

6:00 am-7:03 am

2 stops20h 03m

$466

ChicagoKailua-Kona

ORD - KOA

ORDKOA

Chicago O'Hare Intl

Fri 8/1

8:51 pm-2:27 pm

1 stop22h 36m

Kona Intl

Fri 9/5

9:55 pm-3:58 pm

1 stop13h 03m

$630

ChicagoKailua-Kona

ORD - KOA

ORDKOA

Chicago O'Hare Intl

Mon 8/11

8:00 am-3:19 pm

1 stop12h 19m

Kona Intl

Sun 8/17

9:30 pm-2:13 pm

1 stop11h 43m

$633

ChicagoKailua-Kona

ORD - KOA

ORDKOA

Chicago O'Hare Intl

Fri 7/4

5:37 pm-5:33 pm

2 stops28h 56m

Kona Intl

Thu 7/10

9:47 pm-5:20 pm

1 stop14h 33m

$644

ChicagoKailua-Kona

ORD - KOA

ORDKOA

Chicago O'Hare Intl

Wed 7/16

3:18 pm-7:17 am

2 stops20h 59m

Kona Intl

Thu 7/31

6:00 am-2:13 pm

2 stops27h 13m

$645

ChicagoKailua-Kona

MDW - KOA

MDWKOA

Chicago Midway

Tue 8/12

6:04 am-7:00 pm

2 stops17h 56m

Kona Intl

Mon 8/18

8:41 pm-5:37 pm

2 stops15h 56m

$659

ChicagoKailua-Kona

ORD - KOA

ORDKOA

Chicago O'Hare Intl

Fri 7/11

6:00 am-3:19 pm

1 stop14h 19m

Kona Intl

Mon 7/14

8:00 am-11:59 pm

1 stop10h 59m

$705

ChicagoKailua-Kona

MDW - KOA

MDWKOA

Chicago Midway

Fri 8/1

5:30 am-5:55 pm

2 stops17h 25m

Kona Intl

Fri 9/5

9:15 am-5:10 am

2 stops14h 55m

$715

ChicagoHilo

ORD - ITO

ORDITO

Chicago O'Hare Intl

Mon 7/14

3:18 pm-8:08 am

2 stops21h 50m

Hilo Intl

Sun 7/20

6:00 am-6:03 am

2 stops19h 03m

$722

ChicagoKailua-Kona

ORD - KOA

ORDKOA

Chicago O'Hare Intl

Mon 7/14

7:49 pm-11:31 am

2 stops20h 42m

Kona Intl

Mon 7/21

10:15 pm-11:06 pm

2 stops19h 51m

$752

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/15

Showing 1-10 of 31 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 June 16, 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 June 16, 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
10,000 reviews

Food

7.1

Overall

8.0

Boarding

8.1

Comfort

7.8

Crew

8.5

Entertainment

7.1

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
10,000 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Food

7.1

Overall

8.0

Boarding

8.1

Comfort

7.8

Crew

8.5

Entertainment

7.1

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
4,278 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Food

7.1

Overall

8.0

Boarding

8.1

Comfort

7.8

Crew

8.5

Entertainment

7.1

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
7,963 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Food

7.1

Overall

8.0

Boarding

8.1

Comfort

7.8

Crew

8.5

Entertainment

7.1

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
2,500 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Food

7.1

Overall

8.0

Boarding

8.1

Comfort

7.8

Crew

8.5

Entertainment

7.1

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
8,801 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Food

7.1

Overall

8.0

Boarding

8.1

Comfort

7.8

Crew

8.5

Entertainment

7.1

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?

    $233 is the cheapest one-way deal found within the past few days, from American Airlines. You may also be able to find cheap deals on Alaska Airlines and Southwest, with prices starting from $236 and $278, 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
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Midway to Kahului flights
Midway to Lihue flights
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O'Hare Intl to Hilo flights
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Midway to Hilo flights
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Moline to Kahului flights
Evansville to Kahului flights
O'Hare Intl to Kapalua flights
Bloomington to Kahului flights
St. Louis to Hilo flights
Peoria to Kahului flights
O'Hare Intl to Hana flights
O'Hare Intl to Waimea (Big Island) flights
Moline to Kailua-Kona flights
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St. Louis to Waimea (Big Island) flights
Moline to Hilo flights
Bloomington to Lihue flights
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Springfield to Honolulu flights
Champaign to Honolulu flights
Springfield to Lihue 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 June 16, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$364Average$561FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$412Average$693FlexibilityNo cancel feeOn-time71%
Alaska AirlinesCheapest$417Average$791FlexibilityNo cancel feeOn-time75%
United AirlinesCheapest$509Average$875FlexibilityNo cancel feeOn-time69%
Hawaiian AirlinesCheapest$535Average$681FlexibilityNo cancel feeOn-time85%
SouthwestCheapest$547Average$724FlexibilityNo cancel feeOn-time63%

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