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Kailua-Kona

$290+ Cheap flights from Chicago (CHI) to Kailua-Kona (KOA)

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 8/30. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — KOA
Jun 17 — Jun 241
Tue 6/17
Tue 6/24
1 adult, Economy
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Cheapflights Tip: The best prices from Chicago to Kona Intl are usually found in September or April, booked 88 days in advance, depart on a Tuesday or Monday and return on a Monday

Cheap flight deals from Chicago to Kailua-Kona

Discover tips and strategies to find the most affordable flight options for your journey from Chicago (CHI) to Kailua-Kona (KOA). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated June 12, 2025.

Round-trip from

$437
(Delta)

One-way from

$290
(Alaska Airlines)

Popular in

March

Cheapest in

September

Average price

$827
From Chicago (CHI) to Kona Intl
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One-way flight from Chicago (CHI) to Kona Intl
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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 ($22 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 Kailua-Kona

Cheapest flights from Chicago to Kailua-Kona
Explore the most affordable flight options available from Chicago to Kailua-Kona. Find the lowest fares from popular airlines and budget airlines, with prices last updated on June 12, 2025.

This Delta deal was found by Cheapflights users on 6/10. 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 9/97:15 amORD - KOA
1 stop15h 19mDelta
Thu 9/189:45 pmKOA - ORD
1 stop10h 43mDelta
Deal found 6/10$437
This American Airlines deal was found by Cheapflights users on 6/11. 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.
Wed 10/295:00 amORD - KOA
2 stops13h 46mAmerican Airlines
Tue 11/49:25 pmKOA - ORD
1 stop10h 51mAmerican Airlines
Deal found 6/11$442
This Alaska Airlines deal was found by Cheapflights users on 6/11. 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 10/206:00 amORD - KOA
2 stops13h 49mAlaska Airlines
Tue 10/286:11 pmKOA - ORD
2 stops22h 28mAlaska Airlines
Deal found 6/11$479
This Southwest deal was found by Cheapflights users on 6/10. 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 9/166:10 amMDW - KOA
1 stop11h 00mSouthwest
Mon 9/228:30 pmKOA - MDW
1 stop10h 15mSouthwest
Deal found 6/10$560
This Hawaiian Airlines deal was found by Cheapflights users on 6/10. 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 Hawaiian Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/168:00 amORD - KOA
1 stop13h 34mHawaiian Airlines
Mon 9/228:00 amKOA - ORD
1 stop10h 59mHawaiian Airlines
Deal found 6/10$606
This Delta deal was found by Cheapflights users on 6/11. 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 9/26:00 amMDW - KOA
2 stops18h 00mDelta
Tue 9/98:41 pmKOA - MDW
2 stops16h 56mDelta
Deal found 6/11$641
This Trip.com deal was found by Cheapflights users on 6/10. 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.
Sat 7/267:49 pmORD - KOA
2 stops16h 28mMultiple Airlines
Sat 8/26:00 amKOA - ORD
2 stops19h 03mMultiple Airlines
Deal found 6/10$661

Cheapflights Fare Finder

Customize your flight search to find flights from Chicago to Kailua-Kona 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 12, 2025.
Use the filters below to find and compare flights from Chicago to Kailua-Kona that are best for you.

Fly from

Chicago

Fly to

Kailua-Kona

Route

Depart

Return

Price

ChicagoKailua-Kona

ORD - KOA

ORDKOA

Chicago O'Hare Intl

Tue 9/9

7:15 am-5:34 pm

1 stop15h 19m

Kona Intl

Thu 9/18

9:45 pm-1:28 pm

1 stop10h 43m

$437

ChicagoKailua-Kona

ORD - KOA

ORDKOA

Chicago O'Hare Intl

Tue 9/9

6:20 am-10:13 pm

2 stops20h 53m

Kona Intl

Mon 9/15

9:32 pm-7:03 am

1 stop28h 31m

$497

ChicagoKailua-Kona

ORD - KOA

ORDKOA

Chicago O'Hare Intl

Mon 9/1

5:00 am-2:04 pm

1 stop14h 04m

Kona Intl

Tue 9/9

9:55 pm-5:18 pm

2 stops14h 23m

$515

ChicagoKailua-Kona

ORD - KOA

ORDKOA

Chicago O'Hare Intl

Sun 8/24

7:15 am-3:46 pm

1 stop13h 31m

Kona Intl

Sat 8/30

1:15 pm-5:23 am

1 stop11h 08m

$590

ChicagoKailua-Kona

MDW - KOA

MDWKOA

Chicago Midway

Tue 9/2

6:00 am-7:00 pm

2 stops18h 00m

Kona Intl

Tue 9/9

8:41 pm-6:37 pm

2 stops16h 56m

$641

ChicagoKailua-Kona

ORD - KOA

ORDKOA

Chicago O'Hare Intl

Sat 7/26

7:49 pm-7:17 am

2 stops16h 28m

Kona Intl

Sat 8/2

6:00 am-6:03 am

2 stops19h 03m

$661

ChicagoKailua-Kona

MDW - KOA

MDWKOA

Chicago Midway

Wed 8/20

8:40 am-6:10 pm

2 stops14h 30m

Kona Intl

Fri 8/29

9:15 am-5:10 am

2 stops14h 55m

$663

ChicagoKailua-Kona

ORD - KOA

ORDKOA

Chicago O'Hare Intl

Sat 7/26

3:09 pm-10:04 pm

1 stop11h 55m

Kona Intl

Sat 8/2

9:30 pm-5:40 am

1 stop27h 10m

$789

ChicagoKailua-Kona

ORD - KOA

ORDKOA

Chicago O'Hare Intl

Sat 8/30

2:07 pm-11:16 am

2 stops26h 09m

$290

ChicagoKailua-Kona

ORD - KOA

ORDKOA

Chicago O'Hare Intl

Sat 8/30

7:15 am-5:34 pm

1 stop15h 19m

$308

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/9

Showing 1-10 of 16 results
1
2

Best time to book a flight from Chicago to Kailua-Kona

Have a flexible travel schedule? Discover the best time to fly to Kailua-Kona 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 Kailua-Kona

How far ahead should I book a flight from Chicago to Kailua-Kona?

Use this chart to determine the optimal time to book a round-trip flight from Chicago to Kailua-Kona. Price data was last updated on June 9, 2025.

Booking 88 days in advance of your planned departure date is, on average, the best time to get cheap flights from Chicago to Kailua-Kona. The general trend is that the closer you book to the departure date, the more expensive your flight will be.

What is the cheapest month to book a flight from Chicago to Kailua-Kona?

Currently, October is the cheapest month in which you can book a flight from Chicago to Kailua-Kona (average of $409). Flying from Chicago to Kailua-Kona 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 KOA?

Find hourly flight availability from Chicago to Kailua-Kona. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated June 12, 2025.

When flying from Chicago to Kailua-Kona, the time of day you fly usually plays a role in the price. Save by searching for a flight in the afternoon, which can drop the price by up to 42% versus a flight in the morning.

Rainfall in Kailua-Kona by month

Plan your trip to Kailua-Kona by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Kailua-Kona 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 Kailua-Kona when rainfall is around 1.6 in.

Temperature in Kailua-Kona by month

Plan your trip to Kailua-Kona by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Kailua-Kona, 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 Kailua-Kona

Get insights into the airlines that provide service to Kailua-Kona. 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 Kailua-Kona. Reviews last updated June 12, 2025.
Peruse reviews from past customers who have flown with Alaska Airlines, Southwest and Delta from Chicago to Kailua-Kona to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Alaska Airlines
8.0
Very good
10,000 reviews

Entertainment

7.1

Crew

8.5

Overall

8.0

Comfort

7.8

Boarding

8.1

Food

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

Entertainment

7.1

Crew

8.5

Overall

8.0

Comfort

7.8

Boarding

8.1

Food

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
4,287 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Entertainment

7.1

Crew

8.5

Overall

8.0

Comfort

7.8

Boarding

8.1

Food

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
7,950 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Entertainment

7.1

Crew

8.5

Overall

8.0

Comfort

7.8

Boarding

8.1

Food

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
2,494 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Entertainment

7.1

Crew

8.5

Overall

8.0

Comfort

7.8

Boarding

8.1

Food

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
8,790 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Entertainment

7.1

Crew

8.5

Overall

8.0

Comfort

7.8

Boarding

8.1

Food

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 Kailua-Kona. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly into for flights to Kailua-Kona from Chicago?

    Kona Intl (KOA), located 7.7 mi from the city center, is the airport you fly into when you book flights from Chicago to Kailua-Kona. 6 airlines have flights to Kona Intl from Chicago on a regular basis. Booking flights from Chicago to Kona Intl should not be difficult; the airport handles an average of 0 inbound flights from Chicago per day.

  • What are the cheapest airlines flying from Chicago to Kailua-Kona round-trip?

    Cheapflights users have booked flights from Chicago to Kailua-Kona round-trip from $437. Other airlines that can offer you cheap pricing are American Airlines, from $442, and Alaska Airlines, from $479. Delta is currently priced 37% below the average price you’ll pay for this route.

  • What are the cheapest airlines to fly from Chicago to Kailua-Kona one-way?

    $290 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 American Airlines, with prices starting from $308 and $312, respectively.

  • Where are the most common layover locations when flying from Chicago to Kailua-Kona?

    Flights departing from Chicago and landing in Kailua-Kona layover in Seattle most frequently.

  • What are some popular things to do or see while on a layover in Seattle?

    Most Seattle visitors opt to spend their time experiencing Pike Place Market, Space Needle, and Seattle Waterfront. Pike Place Market, Space Needle, and Seattle Waterfront are located about 11.2 mi, 12.0 mi, and 10.9 mi, respectively from Seattle/Tacoma Intl. Travelers in need of a car in Seattle can rent one for about $55 per day.

  • Where are the least popular layover locations for Chicago to Kailua-Kona flights?

    Chicago to Kailua-Kona flights have a layover in Los Angeles least often.

  • Can I find deals for flights from Chicago to Kailua-Kona that include hotel bookings?

    Yes. In addition to deals on Chicago to Kailua-Kona flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Chicago to Kailua-Kona?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Chicago to Kailua-Kona.

  • Can I find deals for business class flights from Chicago to Kailua-Kona?

    Yes. Cheapflights offers flight deals from Chicago to Kailua-Kona 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 Kailua-Kona?

    Currently, October is the cheapest month in which you can book a flight from Chicago to Kailua-Kona (average of $409). Flying from Chicago to Kailua-Kona 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 Kailua-Kona

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 Kailua-Kona

Discover the top 6 airlines that operate flights from Chicago to Kailua-Kona. 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 12, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$364Average$564FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$412Average$695FlexibilityNo cancel feeOn-time71%
Alaska AirlinesCheapest$417Average$646FlexibilityNo cancel feeOn-time75%
United AirlinesCheapest$509Average$792FlexibilityNo cancel feeOn-time69%
Hawaiian AirlinesCheapest$535Average$728FlexibilityNo cancel feeOn-time85%
SouthwestCheapest$547Average$705FlexibilityNo cancel feeOn-time63%

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