HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Kailua-Kona

$265+ 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 5/14. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — KOA
Apr 29 — May 61
Tue 4/29
Tue 5/6
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Chicago to Kailua-Kona with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

Cheapflights Tip: The best prices from Chicago to Kona Intl are usually found in September or November, booked 76 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 April 24, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$547
(Delta)

One-way from

$265
(Delta)

Popular in

December

Cheapest in

September

Average price

$604
Provider with most accurate pricing for Chicago (CHI)-Kona Intl flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago (CHI)-Kona Intl flights.
Search Deals
From Chicago (CHI) to Kona Intl
Search Deals
One-way flight from Chicago (CHI) to Kona Intl
Search Deals
Highest demand for flights based on searches. 2% potential increase in price ($18 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($24 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in April 2025
Search Deals

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 April 24, 2025.

This Delta deal was found by Cheapflights users on 4/23. 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 5/156:24 amORD - KOA
2 stops17h 46mDelta
Tue 5/209:39 pmKOA - ORD
1 stop10h 51mDelta
Deal found 4/23$547
This United Airlines deal was found by Cheapflights users on 4/21. 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 6/31:55 pmORD - KOA
1 stop11h 08mUnited Airlines
Tue 6/101:05 pmKOA - ORD
1 stop12h 14mUnited Airlines
Deal found 4/21$555
This Delta deal was found by Cheapflights users on 4/21. 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 6/39:16 amMDW - KOA
2 stops14h 54mDelta
Tue 6/108:35 pmKOA - MDW
2 stops16h 05mDelta
Deal found 4/21$558
This Alaska Airlines deal was found by Cheapflights users on 4/22. 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 5/288:00 amORD - KOA
2 stops18h 10mAlaska Airlines
Tue 6/310:09 amKOA - ORD
2 stops14h 31mAlaska Airlines
Deal found 4/22$571
This Southwest deal was found by Cheapflights users on 4/22. 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 8/266:10 amMDW - KOA
1 stop11h 00mSouthwest
Tue 9/28:30 pmKOA - MDW
1 stop10h 15mSouthwest
Deal found 4/22$583
This American Airlines deal was found by Cheapflights users on 4/23. 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 5/137:06 amORD - KOA
1 stop12h 31mAmerican Airlines
Wed 5/211:47 pmKOA - ORD
1 stop11h 06mAmerican Airlines
Deal found 4/23$602

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 April 24, 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

Thu 5/15

6:24 am-7:10 pm

2 stops17h 46m

Kona Intl

Tue 5/20

9:39 pm-1:30 pm

1 stop10h 51m

$547

ChicagoKailua-Kona

MDW - KOA

MDWKOA

Chicago Midway

Tue 6/3

9:16 am-7:10 pm

2 stops14h 54m

Kona Intl

Tue 6/10

8:35 pm-5:40 pm

2 stops16h 05m

$558

ChicagoKailua-Kona

ORD - KOA

ORDKOA

Chicago O'Hare Intl

Tue 6/3

7:51 pm-10:15 pm

1 stop31h 24m

Kona Intl

Tue 6/10

9:20 am-5:40 am

2 stops15h 20m

$573

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

Thu 6/5

5:30 am-12:10 pm

1 stop11h 40m

Kona Intl

Sun 6/8

8:20 pm-12:10 pm

1 stop10h 50m

$763

ChicagoKailua-Kona

ORD - KOA

ORDKOA

Chicago O'Hare Intl

Fri 5/23

9:09 pm-11:26 am

1 stop19h 17m

Kona Intl

Fri 5/30

1:05 pm-11:32 am

1 stop17h 27m

$893

ChicagoKailua-Kona

ORD - KOA

ORDKOA

Chicago O'Hare Intl

Thu 6/5

6:24 am-7:10 pm

2 stops17h 46m

$275

ChicagoKailua-Kona

ORD - KOA

ORDKOA

Chicago O'Hare Intl

Thu 6/5

6:00 am-1:34 pm

1 stop12h 34m

$291

ChicagoKailua-Kona

ORD - KOA

ORDKOA

Chicago O'Hare Intl

Tue 5/6

7:06 am-2:37 pm

1 stop12h 31m

$312

ChicagoKailua-Kona

MDW - KOA

MDWKOA

Chicago Midway

Tue 6/3

9:16 am-7:10 pm

2 stops14h 54m

$317

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/23

Showing 1-10 of 13 results
1
2

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 April.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*2 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars
JustAirTicketPrice Accuracy-Trust Score*3 stars
CheapfaremartPrice Accuracy-Trust Score*1 star
Trip.comPrice Accuracy1 starTrust 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 eDreams the most. eDreams 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?

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 April 18, 2025.

Booking 76 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 April 24, 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 43% versus a flight in the morning.

What is the cheapest day to fly from Chicago to Kailua-Kona?

Use this chart to determine the cheapest time to fly round-trip from Chicago to Kailua-Kona. Price data was last updated on December 16, 2024.

Travelers seeking maximum savings on their Chicago to Kailua-Kona flight should consider departing on Tuesday afternoons when fares are most often at their lowest. Saturday mornings flights should be avoided if possible as fares are typically the most expensive at this time.

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 April 24, 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
9,918 reviews

Boarding

8.2

Overall

8.0

Crew

8.5

Entertainment

7.1

Comfort

7.9

Food

7.1

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >
Alaska Airlines
8.0
Very good
9,918 reviews
Alaska Airlines
8.0
Very good
9,918 reviews

Boarding

8.2

Overall

8.0

Crew

8.5

Entertainment

7.1

Comfort

7.9

Food

7.1

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >
Southwest
8.0
Very good
4,286 reviews
Alaska Airlines
8.0
Very good
9,918 reviews

Boarding

8.2

Overall

8.0

Crew

8.5

Entertainment

7.1

Comfort

7.9

Food

7.1

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >
Delta
8.0
Very good
7,920 reviews
Alaska Airlines
8.0
Very good
9,918 reviews

Boarding

8.2

Overall

8.0

Crew

8.5

Entertainment

7.1

Comfort

7.9

Food

7.1

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >
Hawaiian Airlines
7.9
Good
2,393 reviews
Alaska Airlines
8.0
Very good
9,918 reviews

Boarding

8.2

Overall

8.0

Crew

8.5

Entertainment

7.1

Comfort

7.9

Food

7.1

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >
United Airlines
7.4
Good
8,685 reviews
Alaska Airlines
8.0
Very good
9,918 reviews

Boarding

8.2

Overall

8.0

Crew

8.5

Entertainment

7.1

Comfort

7.9

Food

7.1

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >

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 $547. Other airlines that can offer you cheap pricing are Alaska Airlines, from $569, and American Airlines, from $602. Delta is currently priced 21% below the average price you’ll pay for this route.

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

    $265 is the cheapest one-way deal found within the past few days, from Delta. You may also be able to find cheap deals on American Airlines and Alaska Airlines, with prices starting from $278 and $280, 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 Los Angeles most frequently.

  • 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, Hollywood Walk of Fame, and L.A. Live. Hollywood Bowl, Hollywood Walk of Fame, and L.A. Live are located about 12.5 mi, 11.7 mi, and 10.8 mi, respectively from Los Angeles. Travelers in need of a car in Los Angeles can rent one for about $40 per day.

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

    Chicago to Kailua-Kona flights have a layover in Seattle 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

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Chicago to Kailua-Kona

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
O'Hare Intl to Lihue flights
St. Louis to Honolulu flights
Midway to Kahului flights
St. Louis to Kahului flights
Midway to Kailua-Kona flights
Midway to Lihue flights
St. Louis to Lihue flights
St. Louis to Kailua-Kona flights
O'Hare Intl to Hilo flights
Peoria to Honolulu flights
Moline to Honolulu flights
Midway to Hilo flights
Bloomington to Honolulu flights
Champaign to Honolulu flights
Evansville to Honolulu flights
St. Louis to Hilo flights
Decatur to Honolulu flights
O'Hare Intl to Kapalua flights
Moline to Lihue flights
O'Hare Intl to Waimea (Big Island) flights
Peoria to Lihue flights
Moline to Kahului flights
Peoria to Kahului flights
St. Louis to Kapalua flights
O'Hare Intl to Hana flights
Evansville to Lihue flights
Bloomington to Kahului flights
Bloomington to Lihue flights
Evansville to Kahului flights
St. Louis to Waimea (Big Island) flights
Springfield to Lihue flights
St. Louis to Hana flights
Springfield to Kahului flights
Springfield to Honolulu flights
Dubuque to Honolulu flights
Champaign to Kailua-Kona flights
Moline to Kailua-Kona flights
Moline to Hilo flights

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 April 24, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$318Average$582FlexibilityNo cancel feeOn-timeN/A
Alaska AirlinesCheapest$409Average$645FlexibilityNo cancel feeOn-time75%
American AirlinesCheapest$413Average$690FlexibilityNo cancel feeOn-time71%
Hawaiian AirlinesCheapest$445Average$788FlexibilityNo cancel feeOn-time85%
United AirlinesCheapest$511Average$782FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$593Average$673FlexibilityNo cancel feeOn-time63%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.