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The Big Island

$225+ 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 10/29. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — KOA
Jul 8 — Jul 151
Tue 7/8
Tue 7/15
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 July 3, 2025.

Round-trip from

$465
(Delta)

One-way from

$225
(Alaska Airlines)

Popular in

March

Cheapest in

September

Average price

$716
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. 3% potential increase in price ($24 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 July 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 July 3, 2025.

This Alaska Airlines deal was found by Cheapflights users on 7/2. 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 11/107:55 pmORD - KOA
1 stop22h 48mAlaska Airlines
Tue 11/1812:04 pmKOA - ORD
1 stop21h 50mAlaska Airlines
Deal found 7/2$464
This Delta deal was found by Cheapflights users on 7/2. 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 8/267:15 amORD - KOA
1 stop15h 19mDelta
Thu 9/119:30 pmKOA - ORD
1 stop11h 00mDelta
Deal found 7/2$465
This American Airlines deal was found by Cheapflights users on 7/1. 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.
Mon 8/186:00 amORD - KOA
1 stop12h 29mAmerican Airlines
Mon 8/252:59 pmKOA - ORD
2 stops14h 02mAmerican Airlines
Deal found 7/1$472
This Alaska Airlines deal was found by Cheapflights users on 7/2. 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 10/68:20 amORD - ITO
2 stops17h 11mAlaska Airlines
Fri 10/318:55 amITO - ORD
2 stops16h 27mAlaska Airlines
Deal found 7/2$475
This Southwest deal was found by Cheapflights users on 7/2. 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 10/86:15 amORD - KOA
1 stop11h 45mSouthwest
Wed 10/228:30 pmKOA - ORD
1 stop12h 55mSouthwest
Deal found 7/2$493
This Southwest deal was found by Cheapflights users on 7/2. 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 9/45:15 amMDW - KOA
1 stop11h 55mSouthwest
Fri 9/128:30 pmKOA - MDW
1 stop10h 25mSouthwest
Deal found 7/2$510
This Delta deal was found by Cheapflights users on 7/3. 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 9/46:00 amMDW - KOA
2 stops18h 00mDelta
Fri 9/128:44 pmKOA - MDW
2 stops16h 51mDelta
Deal found 7/3$634
This Southwest deal was found by Cheapflights users on 7/3. 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 8/206:15 amORD - ITO
2 stops16h 55mSouthwest
Tue 8/266:00 amITO - ORD
2 stops12h 40mSouthwest
Deal found 7/3$647
This Southwest deal was found by Cheapflights users on 7/3. 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.
Sun 8/178:00 amMDW - ITO
2 stops15h 10mSouthwest
Sat 8/236:00 amITO - MDW
2 stops12h 05mSouthwest
Deal found 7/3$774
This United Airlines deal was found by Cheapflights users on 7/3. 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.
Tue 9/94:30 pmORD - ITO
2 stops54h 09mUnited Airlines
Wed 9/176:00 amITO - ORD
1 stop19h 23mUnited Airlines
Deal found 7/3$784
This Expedia deal was found by Cheapflights users on 7/3. 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.
Fri 11/146:00 amORD - MUE
2 stops17h 13mMultiple Airlines
Fri 11/217:17 amMUE - ORD
2 stops17h 47mMultiple Airlines
Deal found 7/3$795
This Delta deal was found by Cheapflights users on 6/30. 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.
Sat 9/279:35 amMDW - ITO
2 stops39h 55mDelta
Mon 9/299:43 amITO - MDW
2 stops26h 52mDelta
Deal found 6/30$924

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 July 3, 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

Tue 8/26

7:15 am-5:34 pm

1 stop15h 19m

Kona Intl

Thu 9/11

9:30 pm-1:30 pm

1 stop11h 00m

$465

ChicagoKailua-Kona

ORD - KOA

ORDKOA

Chicago O'Hare Intl

Tue 8/26

8:00 am-3:55 pm

1 stop12h 55m

Kona Intl

Sat 9/6

6:00 am-12:04 am

2 stops13h 04m

$470

ChicagoKailua-Kona

ORD - KOA

ORDKOA

Chicago O'Hare Intl

Mon 8/18

6:00 am-1:29 pm

1 stop12h 29m

Kona Intl

Mon 8/25

2:59 pm-10:01 am

2 stops14h 02m

$472

ChicagoHilo

ORD - ITO

ORDITO

Chicago O'Hare Intl

Sat 9/27

7:00 am-4:56 pm

2 stops14h 56m

Hilo Intl

Mon 9/29

5:26 pm-2:24 pm

2 stops15h 58m

$476

ChicagoKailua-Kona

MDW - KOA

MDWKOA

Chicago Midway

Thu 9/4

5:15 am-12:10 pm

1 stop11h 55m

Kona Intl

Fri 9/12

8:30 pm-11:55 am

1 stop10h 25m

$510

ChicagoKailua-Kona

MDW - KOA

MDWKOA

Chicago Midway

Thu 9/4

6:00 am-7:00 pm

2 stops18h 00m

Kona Intl

Fri 9/12

8:44 pm-6:35 pm

2 stops16h 51m

$634

ChicagoHilo

ORD - ITO

ORDITO

Chicago O'Hare Intl

Wed 8/20

6:15 am-6:10 pm

2 stops16h 55m

Hilo Intl

Tue 8/26

6:00 am-11:40 pm

2 stops12h 40m

$647

ChicagoHilo

MDW - ITO

MDWITO

Chicago Midway

Sun 8/17

8:00 am-6:10 pm

2 stops15h 10m

Hilo Intl

Sat 8/23

6:00 am-11:05 pm

2 stops12h 05m

$774

ChicagoHilo

ORD - ITO

ORDITO

Chicago O'Hare Intl

Tue 9/9

4:30 pm-5:39 pm

2 stops54h 09m

Hilo Intl

Wed 9/17

6:00 am-6:23 am

1 stop19h 23m

$784

ChicagoWaimea (Big Island)

ORD - MUE

ORDMUE

Chicago O'Hare Intl

Sat 8/16

7:18 pm-6:53 am

2 stops40h 35m

Waimea (Big Island) Waimea Kohala

Sat 8/23

7:17 am-7:03 am

2 stops18h 46m

$892

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/3

Showing 1-10 of 23 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 July 3, 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 July 3, 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

Comfort

7.8

Food

7.1

Overall

8.0

Crew

8.5

Entertainment

7.1

Boarding

8.1

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

Comfort

7.8

Food

7.1

Overall

8.0

Crew

8.5

Entertainment

7.1

Boarding

8.1

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
4,266 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Comfort

7.8

Food

7.1

Overall

8.0

Crew

8.5

Entertainment

7.1

Boarding

8.1

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
7,982 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Comfort

7.8

Food

7.1

Overall

8.0

Crew

8.5

Entertainment

7.1

Boarding

8.1

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
8,861 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Comfort

7.8

Food

7.1

Overall

8.0

Crew

8.5

Entertainment

7.1

Boarding

8.1

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
American Airlines
7.2
Good
10,000 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Comfort

7.8

Food

7.1

Overall

8.0

Crew

8.5

Entertainment

7.1

Boarding

8.1

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?

    $225 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 Southwest and American Airlines, with prices starting from $233 and $317, 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
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O'Hare Intl to Waimea (Big Island) 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 July 3, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$364Average$614FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$414Average$694FlexibilityNo cancel feeOn-time71%
Alaska AirlinesCheapest$416Average$792FlexibilityNo cancel feeOn-time75%
United AirlinesCheapest$507Average$846FlexibilityNo cancel feeOn-time69%
Hawaiian AirlinesCheapest$535Average$681FlexibilityNo cancel feeOn-time85%
SouthwestCheapest$547Average$724FlexibilityNo cancel feeOn-time63%

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