Kailua-Kona

$247+ 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 8/19. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — KOA
Jun 10 — Jun 171
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Cheap 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 May 11, 2026.

This Alaska Airlines deal was found by Cheapflights users on 5/8. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/252:18 pm
ORD
-
KOA
1 stop29h 33m
Alaska Airlines
Thu 8/2710:35 am
KOA
-
ORD
1 stop21h 47m
Alaska Airlines
Deal found 5/8$494
This Alaska Airlines deal was found by Cheapflights users on 5/8. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/192:18 pm
ORD
-
KOA
1 stop29h 33m
Multiple Airlines
Fri 9/256:00 am
KOA
-
ORD
2 stops12h 57m
Multiple Airlines
Deal found 5/8$499
This Delta deal was found by Cheapflights users on 5/8. 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 8/257:45 am
ORD
-
KOA
2 stops14h 50m
Delta
Thu 8/279:55 pm
KOA
-
ORD
1 stop10h 46m
Delta
Deal found 5/8$500
This Southwest deal was found by Cheapflights users on 5/7. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/238:50 pm
MDW
-
KOA
2 stops20h 50m
Southwest
Wed 9/3010:00 am
KOA
-
MDW
1 stop14h 45m
Southwest
Deal found 5/7$505
This United Airlines deal was found by Cheapflights users on 5/8. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/26:03 am
ORD
-
KOA
1 stop10h 43m
United Airlines
Wed 9/28:00 pm
KOA
-
ORD
1 stop11h 19m
United Airlines
Deal found 5/8$524
This Alaska Airlines deal was found by Cheapflights users on 5/7. 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.
Mon 8/316:01 am
ORD
-
KOA
1 stop13h 50m
Multiple Airlines
Wed 9/28:18 am
KOA
-
ORD
2 stops17h 04m
Multiple Airlines
Deal found 5/7$530
This Delta deal was found by Cheapflights users on 5/9. 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 8/115:28 am
ORD
-
KOA
2 stops18h 49m
Delta
Wed 8/269:06 pm
KOA
-
ORD
1 stop11h 17m
Delta
Deal found 5/9$531
This Expedia deal was found by Cheapflights users on 5/5. 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.
Wed 9/237:00 am
ORD
-
KOA
2 stops13h 47m
Multiple Airlines
Wed 9/3010:51 am
KOA
-
ORD
2 stops14h 31m
Multiple Airlines
Deal found 5/5$535
This Southwest deal was found by Cheapflights users on 5/9. 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 8/198:50 pm
MDW
-
KOA
2 stops20h 35m
Southwest
Tue 8/2510:00 am
KOA
-
MDW
1 stop14h 45m
Southwest
Deal found 5/9$535
This United Airlines deal was found by Cheapflights users on 5/8. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/26:00 am
ORD
-
KOA
1 stop10h 42m
United Airlines
Tue 6/91:52 pm
KOA
-
ORD
1 stop11h 01m
United Airlines
Deal found 5/8$536
This Alaska Airlines deal was found by Cheapflights users on 5/9. 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 6/13:28 pm
ORD
-
KOA
1 stop11h 46m
Alaska Airlines
Mon 6/88:00 am
KOA
-
ORD
1 stop10h 59m
Alaska Airlines
Deal found 5/9$540
This Kiwi.com deal was found by Cheapflights users on 5/5. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/27:40 am
ORD
-
KOA
2 stops16h 06m
Multiple Airlines
Tue 6/98:00 am
KOA
-
ORD
1 stop10h 59m
Multiple Airlines
Deal found 5/5$545

Find 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 May 11, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$505
(Southwest)

One-way from

$247
(American Airlines)

Popular in

December

Cheapest in

January

Average price

$732
Provider with most accurate pricing for Chicago (CHI)-Kona Intl flight deals.
Provider most trusted by Cheapflights users for Chicago (CHI)-Kona Intl flights.
From Chicago (CHI) to Kona Intl
One-way flight from Chicago (CHI) to Kona Intl
Highest demand for flights based on searches. 5% potential increase in price ($43 potential increase over avg. RT price).
Cheapest flight prices on average. 4% potential price decrease ($34 potential savings vs. average RT price).
Average for round-trip flights in May 2026

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 May 11, 2026.
Use the filters below to find and compare flights from Chicago to Kailua-Kona that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoKailua-Kona

ORD - KOA

ORDKOA

Chicago O'Hare Intl

Tue 8/25

7:45 am-5:35 pm

2 stops14h 50m

Kona Intl

Thu 8/27

9:55 pm-6:19 pm

2 stops15h 24m

$505

ChicagoKailua-Kona

ORD - KOA

ORDKOA

Chicago O'Hare Intl

Tue 6/2

6:00 am-11:42 am

1 stop10h 42m

Kona Intl

Tue 6/9

7:00 am-10:59 pm

1 stop10h 59m

$570

ChicagoKailua-Kona

ORD - KOA

ORDKOA

Chicago O'Hare Intl

Sat 5/30

7:45 am-7:20 pm

2 stops16h 35m

Kona Intl

Sat 6/6

9:55 pm-1:50 pm

1 stop10h 55m

$602

ChicagoKailua-Kona

ORD - KOA

ORDKOA

Chicago O'Hare Intl

Fri 8/21

2:18 pm-2:51 pm

1 stop29h 33m

Kona Intl

Fri 8/28

10:35 am-1:22 pm

1 stop21h 47m

$613

ChicagoKailua-Kona

ORD - KOA

ORDKOA

Chicago O'Hare Intl

Fri 8/21

7:59 pm-2:51 pm

1 stop23h 52m

Kona Intl

Thu 8/27

10:35 am-1:22 pm

1 stop21h 47m

$613

ChicagoKailua-Kona

ORD - KOA

ORDKOA

Chicago O'Hare Intl

Tue 8/18

7:00 am-5:35 pm

1 stop15h 35m

Kona Intl

Sat 8/22

9:55 pm-1:41 pm

1 stop10h 46m

$614

ChicagoKailua-Kona

ORD - KOA

ORDKOA

Chicago O'Hare Intl

Mon 8/17

2:20 pm-12:15 pm

1 stop26h 55m

Kona Intl

Sat 8/22

6:00 am-11:41 pm

2 stops12h 41m

$619

ChicagoKailua-Kona

ORD - KOA

ORDKOA

Chicago O'Hare Intl

Fri 8/21

8:42 pm-1:38 pm

2 stops21h 56m

Kona Intl

Fri 8/28

10:35 am-1:22 pm

1 stop21h 47m

$620

ChicagoKailua-Kona

ORD - KOA

ORDKOA

Chicago O'Hare Intl

Fri 8/21

8:28 am-7:17 pm

2 stops15h 49m

Kona Intl

Thu 8/27

9:55 pm-1:41 pm

1 stop10h 46m

$620
Quickest round-trip

ChicagoKailua-Kona

ORD - KOA

ORDKOA

Chicago O'Hare Intl

Thu 5/21

6:00 am-11:42 am

1 stop10h 42m

Kona Intl

Wed 5/27

8:00 pm-11:23 am

1 stop10h 23m

$633

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/6

Showing 1-10 of 36 resultsSorted by cheapest first
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Compare providers for flights from Chicago to Kailua-Kona

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Chicago to Kailua-Kona in May.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Chicago-Kailua-Kona flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Chicago-Kailua-Kona flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Chicago-Kailua-Kona flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Chicago-Kailua-Kona flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Chicago-Kailua-Kona flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

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?

Booking 60 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, January is the cheapest month in which you can book a flight from Chicago to Kailua-Kona (average of $262). Flying from Chicago to Kailua-Kona in May is currently the most expensive (average of $444). 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.

How much does it cost to fly round-trip from Chicago to Kailua-Kona?

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 May 11, 2026.
Get a feel of what it's like to fly with Southwest,Alaska Airlines, andDelta from Chicago to Kailua-Kona by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.

Entertainment

7.5

Boarding

8.1

Overall

8.0

Comfort

8.0

Crew

8.6

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.

Entertainment

7.5

Boarding

8.1

Overall

8.0

Comfort

8.0

Crew

8.6

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.

Entertainment

7.5

Boarding

8.1

Overall

8.0

Comfort

8.0

Crew

8.6

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.

Entertainment

7.5

Boarding

8.1

Overall

8.0

Comfort

8.0

Crew

8.6

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.

Entertainment

7.5

Boarding

8.1

Overall

8.0

Comfort

8.0

Crew

8.6

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.

Entertainment

7.5

Boarding

8.1

Overall

8.0

Comfort

8.0

Crew

8.6

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.

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. 5 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.

  • How long is the flight from Chicago to Kailua-Kona?

    A quick flight from Chicago to Kailua-Kona can take about 10h 42m. Delta provides one of the quickest options available for as low as $570. The distance from Chicago to Kailua-Kona is about 4205 mi. Both multi-stop and nonstop flights can be found to your destination and back.

  • 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 $343. Other airlines that can offer you cheap pricing are Alaska Airlines, from $418, and Southwest, from $442. Delta is currently priced 54% below the average price you’ll pay for this route.

  • What are the cheapest airlines to fly from Chicago to Kailua-Kona 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 American Airlines and United Airlines, with prices starting from $247 and $366, respectively.

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

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

    Most Los Angeles visitors opt to spend their time experiencing Hollywood Bowl, Little Tokyo, and Hollywood Walk of Fame. Hollywood Bowl, Little Tokyo, and Hollywood Walk of Fame are located about 12.4 mi, 12.2 mi, and 11.7 mi, respectively from Los Angeles. Travelers in need of a car in Los Angeles can rent one for about $42 per day.

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

  • 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, January is the cheapest month in which you can book a flight from Chicago to Kailua-Kona (average of $262). Flying from Chicago to Kailua-Kona in May is currently the most expensive (average of $444). 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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Top 5 airlines flying from Chicago to Kailua-Kona

Discover the top 5 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 May 11, 2026.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$343Average$594FlexibilityNo cancel feeOn-timeN/A
Alaska AirlinesCheapest$418Average$668FlexibilityNo cancel feeOn-time75%
SouthwestCheapest$442Average$813FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$447Average$685FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$447Average$933FlexibilityNo cancel feeOn-time69%

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