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Kailua-Kona

$190+ 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 12/9. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — KOA
Dec 2 — Dec 91
Tue 12/2
Tue 12/9
1 adult, Economy
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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

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3. Compare prices and book

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Cheapflights Tip: The best prices from Chicago to Kona Intl are usually found in September or January, booked 55 days in advance, depart on a Tuesday or Monday and return on a Monday

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 November 2, 2025.

This Alaska Airlines deal was found by Cheapflights users on 11/1. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/88:55 amORD - KOA
1 stop11h 05mAlaska Airlines
Sat 12/139:00 pmKOA - ORD
2 stops22h 50mAlaska Airlines
Deal found 11/1$440
This Alaska Airlines deal was found by Cheapflights users on 10/31. 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.
Thu 12/118:55 amORD - KOA
1 stop11h 05mAlaska Airlines
Thu 12/182:25 pmKOA - ORD
1 stop25h 37mAlaska Airlines
Deal found 10/31$445
This Delta deal was found by Cheapflights users on 10/31. 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 12/117:50 amORD - KOA
1 stop14h 30mDelta
Thu 12/188:43 pmKOA - ORD
2 stops17h 25mDelta
Deal found 10/31$449
This Delta deal was found by Cheapflights users on 10/31. 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.
Mon 11/246:13 pmORD - KOA
1 stop28h 00mDelta
Thu 12/48:43 pmKOA - ORD
1 stop12h 50mDelta
Deal found 10/31$463
This American Airlines deal was found by Cheapflights users on 11/1. 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.
Sat 11/298:30 amORD - KOA
1 stop12h 17mAmerican Airlines
Mon 12/89:55 pmKOA - ORD
1 stop10h 00mAmerican Airlines
Deal found 11/1$475
This Delta deal was found by Cheapflights users on 11/1. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/17:20 amORD - KOA
2 stops16h 05mDelta
Tue 12/98:43 pmKOA - ORD
1 stop12h 50mDelta
Deal found 11/1$478
This Alaska Airlines deal was found by Cheapflights users on 10/31. 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 11/246:00 amORD - KOA
2 stops20h 21mAlaska Airlines
Thu 12/42:20 pmKOA - ORD
1 stop19h 49mAlaska Airlines
Deal found 10/31$489
This Southwest deal was found by Cheapflights users on 11/1. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/15:10 amMDW - KOA
2 stops17h 00mSouthwest
Tue 12/99:15 pmKOA - MDW
1 stop12h 25mSouthwest
Deal found 11/1$539
This Southwest deal was found by Cheapflights users on 11/1. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/85:15 amMDW - KOA
1 stop12h 25mSouthwest
Sat 12/139:15 pmKOA - MDW
1 stop11h 50mSouthwest
Deal found 11/1$625
This Delta deal was found by Cheapflights users on 10/31. 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 12/119:59 amMDW - KOA
2 stops13h 31mDelta
Thu 12/181:50 pmKOA - MDW
2 stops16h 04mDelta
Deal found 10/31$641
This Delta deal was found by Cheapflights users on 11/1. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/296:00 amMDW - KOA
2 stops18h 26mDelta
Mon 12/89:30 pmKOA - MDW
2 stops16h 48mDelta
Deal found 11/1$646
This Delta deal was found by Cheapflights users on 11/1. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/296:00 amMDW - KOA
2 stops18h 26mDelta
Tue 12/98:43 pmKOA - MDW
2 stops17h 17mDelta
Deal found 11/1$688

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 November 2, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$393
(Alaska Airlines)

One-way from

$190
(Alaska Airlines)

Popular in

December

Cheapest in

September

Average price

$888

Good one-way deal

$582 or less
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. 11% potential increase in price ($91 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 November 2025
Search Deals
Price to beat on a one-way flight from Chicago (CHI) to Kona Intl.
Search Deals

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 November 2, 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

Mon 1/12

9:00 am-6:26 am

2 stops25h 26m

Kona Intl

Mon 1/26

2:24 pm-11:37 pm

1 stop29h 13m

$399

ChicagoKailua-Kona

ORD - KOA

ORDKOA

Chicago O'Hare Intl

Tue 1/13

9:00 am-3:27 pm

1 stop34h 27m

Kona Intl

Wed 1/21

2:51 pm-11:37 pm

1 stop28h 46m

$403

ChicagoKailua-Kona

ORD - KOA

ORDKOA

Chicago O'Hare Intl

Thu 1/15

3:49 pm-10:44 am

2 stops22h 55m

Kona Intl

Thu 1/22

2:51 pm-2:29 pm

1 stop19h 38m

$440

ChicagoKailua-Kona

ORD - KOA

ORDKOA

Chicago O'Hare Intl

Mon 12/8

3:05 pm-4:00 pm

1 stop28h 55m

Kona Intl

Sat 12/13

2:20 pm-11:50 pm

1 stop29h 30m

$443

ChicagoKailua-Kona

ORD - KOA

ORDKOA

Chicago O'Hare Intl

Thu 12/11

8:50 am-7:30 pm

2 stops14h 40m

Kona Intl

Thu 12/18

8:43 pm-6:08 pm

2 stops17h 25m

$454

ChicagoKailua-Kona

ORD - KOA

ORDKOA

Chicago O'Hare Intl

Thu 1/15

7:30 am-6:47 pm

1 stop15h 17m

Kona Intl

Thu 1/22

8:45 pm-1:22 pm

1 stop12h 37m

$464

ChicagoKailua-Kona

ORD - KOA

ORDKOA

Chicago O'Hare Intl

Sat 11/29

8:30 am-4:47 pm

1 stop12h 17m

Kona Intl

Mon 12/8

9:55 pm-11:55 am

1 stop10h 00m

$475

ChicagoKailua-Kona

ORD - KOA

ORDKOA

Chicago O'Hare Intl

Thu 1/15

3:49 pm-10:44 am

2 stops22h 55m

Kona Intl

Sun 1/25

1:43 pm-2:29 pm

2 stops20h 46m

$476

ChicagoKailua-Kona

ORD - KOA

ORDKOA

Chicago O'Hare Intl

Mon 12/1

7:20 am-7:25 pm

2 stops16h 05m

Kona Intl

Mon 12/8

8:43 pm-1:33 pm

1 stop12h 50m

$478

ChicagoKailua-Kona

MDW - KOA

MDWKOA

Chicago Midway

Tue 1/13

6:10 am-1:45 pm

1 stop11h 35m

Kona Intl

Wed 1/21

9:25 pm-2:45 pm

2 stops13h 20m

$586

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/1

Showing 1-10 of 33 results
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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 November.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star
eDreamsPrice Accuracy3 starsTrust Score*3 stars
Trip.comPrice Accuracy2 starsTrust Score*3 stars
CheapfaremartPrice Accuracy-Trust Score*1 star
JustAirTicketPrice Accuracy-Trust Score*1 star

*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 eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Chicago-Kailua-Kona flight deals on Cheapflights vs. eDreams >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 October 31, 2025.

Booking 55 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 $420). Flying from Chicago to Kailua-Kona in July is currently the most expensive (average of $667). 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 November 2, 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 evening, which can drop the price by up to 39% versus a flight in the morning.

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

What’s the top layover airport for flights from Chicago to Kailua-Kona?

Share of 1-stop round-trip flights from Chicago to Kailua-Kona chosen by Cheapflights users in the past 12 months, using the same layover each way.

Seattle (SEA) – chosen by Cheapflights users on 95% of 1-stop itineraries from Chicago to Kailua-Kona on Cheapflights.

What’s the cheapest layover airport for flights from Chicago to Kailua-Kona?

Average round-trip fare for 1-stop flights from Chicago to Kailua-Kona, chosen by Cheapflights users in the past 12 months, with the same layover each way.

Las Vegas (LAS) is the most affordable 1-stop option, with an average round-trip price of $442.

What’s the fastest layover option from Chicago to Kailua-Kona?

Shortest average travel time for 1-stop one-way flights from Chicago to Kailua-Kona, based on itineraries clicked by Cheapflights users over the past 12 months, grouped by layover airport.

Flights via Las Vegas (LAS) have the shortest average one-way travel time for 1-stop routes: 10h 55m.

Which airport typically offers the quickest layover for flights from Chicago to Kailua-Kona?

Average layover duration for 1-stop one-way flights from Chicago to Kailua-Kona, chosen by Cheapflights users in the last 12 months, grouped by stopover airport.

Flights via Las Vegas (LAS) offer the fastest connection on this route, with an average layover time of 2h 10m.

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 November 2, 2025.
Get a feel of what it's like to fly with Alaska Airlines, Southwest, and Delta 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.
Alaska Airlines
8.0
Very good
11,232 reviews

Overall

8.0

Food

7.1

Crew

8.5

Entertainment

7.0

Boarding

8.1

Comfort

7.8

Reviews

1 / 20
10.0
Excellent

Anonymous,Sep 2025

BOS - HNL

The flight was awesome but a little long. I would prefer a flight with a layover. The amount of space available was minimal and a little uncomfortable for that long of a flight.
Alaska Airlines
8.0
Very good
11,232 reviews
Alaska Airlines
8.0
Very good
11,232 reviews

Overall

8.0

Food

7.1

Crew

8.5

Entertainment

7.0

Boarding

8.1

Comfort

7.8

Reviews

1 / 20
10.0
Excellent

Anonymous,Sep 2025

BOS - HNL

The flight was awesome but a little long. I would prefer a flight with a layover. The amount of space available was minimal and a little uncomfortable for that long of a flight.
Southwest
8.0
Very good
4,241 reviews
Alaska Airlines
8.0
Very good
11,232 reviews

Overall

8.0

Food

7.1

Crew

8.5

Entertainment

7.0

Boarding

8.1

Comfort

7.8

Reviews

1 / 20
10.0
Excellent

Anonymous,Sep 2025

BOS - HNL

The flight was awesome but a little long. I would prefer a flight with a layover. The amount of space available was minimal and a little uncomfortable for that long of a flight.
Delta
7.9
Good
7,997 reviews
Alaska Airlines
8.0
Very good
11,232 reviews

Overall

8.0

Food

7.1

Crew

8.5

Entertainment

7.0

Boarding

8.1

Comfort

7.8

Reviews

1 / 20
10.0
Excellent

Anonymous,Sep 2025

BOS - HNL

The flight was awesome but a little long. I would prefer a flight with a layover. The amount of space available was minimal and a little uncomfortable for that long of a flight.
United Airlines
7.4
Good
8,994 reviews
Alaska Airlines
8.0
Very good
11,232 reviews

Overall

8.0

Food

7.1

Crew

8.5

Entertainment

7.0

Boarding

8.1

Comfort

7.8

Reviews

1 / 20
10.0
Excellent

Anonymous,Sep 2025

BOS - HNL

The flight was awesome but a little long. I would prefer a flight with a layover. The amount of space available was minimal and a little uncomfortable for that long of a flight.
American Airlines
7.2
Good
11,033 reviews
Alaska Airlines
8.0
Very good
11,232 reviews

Overall

8.0

Food

7.1

Crew

8.5

Entertainment

7.0

Boarding

8.1

Comfort

7.8

Reviews

1 / 20
10.0
Excellent

Anonymous,Sep 2025

BOS - HNL

The flight was awesome but a little long. I would prefer a flight with a layover. The amount of space available was minimal and a little uncomfortable for that long of a flight.

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.

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

    A quick flight from Chicago to Kailua-Kona can take about 11h 35m. Alaska Airlines provides one of the quickest options available for as low as $586. The distance from Chicago to Kailua-Kona is about 4213 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 $371. Other airlines that can offer you cheap pricing are Hawaiian Airlines, from $429, and Alaska Airlines, from $441. Delta is currently priced 49% below the average price you’ll pay for this route.

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

    $190 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 Southwest, with prices starting from $227 and $357, respectively.

  • What are the cheapest flights from Chicago to Kailua-Kona?

    Looking for the cheapest flight from Chicago to Kailua-Kona? While on average our users pay $582, our data indicates the cheapest price to be $582. The most popular route (Chicago O'Hare Intl - Kona Intl), is priced around $437.

  • 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 $43 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, January is the cheapest month in which you can book a flight from Chicago to Kailua-Kona (average of $420). Flying from Chicago to Kailua-Kona in July is currently the most expensive (average of $667). 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

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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 November 2, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$371Average$668FlexibilityNo cancel feeOn-timeN/A
Hawaiian AirlinesCheapest$429Average$651FlexibilityNo cancel feeOn-time85%
Alaska AirlinesCheapest$441Average$663FlexibilityNo cancel feeOn-time75%
United AirlinesCheapest$447Average$738FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$467Average$736FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$593Average$717FlexibilityNo cancel feeOn-time63%

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