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Kailua-Kona

$224+ 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 2/9. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — KOA
oct. 15 — oct. 221
mié. 10/15
mié. 10/22
1 adult, Economy
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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

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 septiembre 15, 2025.

Round-trip from

$440
(Delta)

One-way from

$224
(American Airlines)

Popular in

December

Cheapest in

September

Average price

$577
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. 6% potential increase in price ($53 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($29 potential savings vs. average RT price).
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Average for round-trip flights in September 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 septiembre 15, 2025.

This Delta deal was found by Cheapflights users on 9/13. 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.
mié. 10/87:37 amORD - KOA
2 stops16h 46mDelta
mié. 10/229:30 pmKOA - ORD
1 stop11h 00mDelta
Deal found 9/13$440
This Delta deal was found by Cheapflights users on 9/13. 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.
vie. 10/317:37 amORD - KOA
1 stop14h 53mDelta
lun. 11/108:30 pmKOA - ORD
1 stop13h 04mDelta
Deal found 9/13$441
This Delta deal was found by Cheapflights users on 9/14. 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.
mié. 10/227:37 amORD - KOA
1 stop14h 53mDelta
lun. 10/279:30 pmKOA - ORD
1 stop11h 00mDelta
Deal found 9/14$447
This Alaska Airlines deal was found by Cheapflights users on 9/13. 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.
lun. 10/277:59 pmORD - KOA
1 stop22h 44mAlaska Airlines
vie. 10/3111:09 amKOA - ORD
1 stop21h 45mAlaska Airlines
Deal found 9/13$451
This Alaska Airlines deal was found by Cheapflights users on 9/13. 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.
mié. 10/228:00 amORD - KOA
2 stops18h 14mAlaska Airlines
mar. 11/48:45 amKOA - ORD
1 stop11h 39mAlaska Airlines
Deal found 9/13$452
This Delta deal was found by Cheapflights users on 9/13. 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.
lun. 10/277:37 amORD - KOA
2 stops16h 46mDelta
vie. 10/319:30 pmKOA - ORD
1 stop14h 48mDelta
Deal found 9/13$456
This Alaska Airlines deal was found by Cheapflights users on 9/12. 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.
lun. 10/277:00 amORD - KOA
2 stops15h 32mAlaska Airlines
dom. 11/212:09 pmKOA - ORD
1 stop21h 45mAlaska Airlines
Deal found 9/12$457
This Alaska Airlines deal was found by Cheapflights users on 9/14. 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.
mié. 10/228:00 amORD - KOA
2 stops17h 27mAlaska Airlines
lun. 10/277:13 pmKOA - ORD
2 stops16h 17mAlaska Airlines
Deal found 9/14$458
This Southwest deal was found by Cheapflights users on 9/13. 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.
jue. 11/275:55 amMDW - KOA
1 stop11h 05mSouthwest
sáb. 12/69:15 pmKOA - MDW
2 stops15h 05mSouthwest
Deal found 9/13$482
This Southwest deal was found by Cheapflights users on 9/14. 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.
mié. 10/226:05 amMDW - KOA
1 stop11h 55mSouthwest
lun. 10/278:30 pmKOA - MDW
1 stop13h 40mSouthwest
Deal found 9/14$485
This Southwest deal was found by Cheapflights users on 9/14. 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.
mié. 10/296:05 amMDW - KOA
1 stop11h 55mSouthwest
mié. 11/59:15 pmKOA - MDW
2 stops15h 05mSouthwest
Deal found 9/14$513
This Delta deal was found by Cheapflights users on 9/14. 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.
mié. 10/299:35 amMDW - KOA
2 stops14h 48mDelta
mié. 11/59:30 pmKOA - MDW
2 stops16h 13mDelta
Deal found 9/14$526

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 septiembre 15, 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

mié. 10/8

7:37 am-7:23 pm

2 stops16h 46m

Kona Intl

mié. 10/22

8:30 pm-5:10 pm

2 stops15h 40m

$445

ChicagoKailua-Kona

ORD - KOA

ORDKOA

Chicago O'Hare Intl

lun. 2/2

2:00 pm-10:35 pm

1 stop12h 35m

Kona Intl

lun. 2/9

8:00 am-11:59 pm

1 stop11h 59m

$447

ChicagoKailua-Kona

ORD - KOA

ORDKOA

Chicago O'Hare Intl

mar. 2/24

12:45 pm-8:51 pm

1 stop12h 06m

Kona Intl

mié. 3/4

8:55 pm-11:42 am

1 stop10h 47m

$447

ChicagoKailua-Kona

ORD - KOA

ORDKOA

Chicago O'Hare Intl

lun. 1/5

7:30 am-6:55 pm

1 stop15h 25m

Kona Intl

lun. 1/12

8:45 pm-1:25 pm

1 stop12h 40m

$447

ChicagoKailua-Kona

ORD - KOA

ORDKOA

Chicago O'Hare Intl

jue. 1/29

2:00 pm-10:35 pm

1 stop12h 35m

Kona Intl

mié. 2/4

10:00 pm-1:04 pm

1 stop11h 04m

$447

ChicagoKailua-Kona

ORD - KOA

ORDKOA

Chicago O'Hare Intl

mar. 1/20

7:30 am-6:55 pm

1 stop15h 25m

Kona Intl

mié. 1/28

8:45 pm-1:25 pm

1 stop12h 40m

$447

ChicagoKailua-Kona

ORD - KOA

ORDKOA

Chicago O'Hare Intl

mar. 1/27

7:30 am-6:55 pm

1 stop15h 25m

Kona Intl

lun. 2/2

9:55 pm-1:25 pm

1 stop11h 30m

$447

ChicagoKailua-Kona

ORD - KOA

ORDKOA

Chicago O'Hare Intl

mar. 1/27

7:30 am-6:55 pm

1 stop15h 25m

Kona Intl

mié. 2/4

9:55 pm-1:25 pm

1 stop11h 30m

$447

ChicagoKailua-Kona

ORD - KOA

ORDKOA

Chicago O'Hare Intl

lun. 1/19

7:30 am-6:55 pm

1 stop15h 25m

Kona Intl

jue. 1/29

8:45 pm-1:25 pm

1 stop12h 40m

$447

ChicagoKailua-Kona

ORD - KOA

ORDKOA

Chicago O'Hare Intl

mié. 2/25

11:05 am-8:51 pm

1 stop13h 46m

Kona Intl

mar. 3/3

10:55 pm-2:50 pm

2 stops11h 55m

$452

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/14

Showing 1-10 of 34 results
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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 September 12, 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, 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 septiembre 15, 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 51% 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 septiembre 15, 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
10,000 reviews

Overall

8.0

Comfort

7.8

Entertainment

7.0

Boarding

8.1

Food

7.1

Crew

8.5

Reviews

1 / 20
6.0
Good

Hannah,Aug 2025

SFO - SAN

Ticket said TSA pre check, but then the TSA agent said that Alaska Airlines has not actually entered the pre check information for the ticket, so I had to use regular security. During boarding, I have a disability and need to board early. The Alaska Airlines employee announced disability boarding, but then immediately announced 2 other groups to board, so I still had to fight the crowds. On the plane, the stewardess was brusk and rude. Seats were very uncomfortable, especially on lower back.
Alaska Airlines
8.0
Very good
10,000 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Overall

8.0

Comfort

7.8

Entertainment

7.0

Boarding

8.1

Food

7.1

Crew

8.5

Reviews

1 / 20
6.0
Good

Hannah,Aug 2025

SFO - SAN

Ticket said TSA pre check, but then the TSA agent said that Alaska Airlines has not actually entered the pre check information for the ticket, so I had to use regular security. During boarding, I have a disability and need to board early. The Alaska Airlines employee announced disability boarding, but then immediately announced 2 other groups to board, so I still had to fight the crowds. On the plane, the stewardess was brusk and rude. Seats were very uncomfortable, especially on lower back.
Southwest
8.0
Very good
4,245 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Overall

8.0

Comfort

7.8

Entertainment

7.0

Boarding

8.1

Food

7.1

Crew

8.5

Reviews

1 / 20
6.0
Good

Hannah,Aug 2025

SFO - SAN

Ticket said TSA pre check, but then the TSA agent said that Alaska Airlines has not actually entered the pre check information for the ticket, so I had to use regular security. During boarding, I have a disability and need to board early. The Alaska Airlines employee announced disability boarding, but then immediately announced 2 other groups to board, so I still had to fight the crowds. On the plane, the stewardess was brusk and rude. Seats were very uncomfortable, especially on lower back.
Delta
8.0
Very good
7,956 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Overall

8.0

Comfort

7.8

Entertainment

7.0

Boarding

8.1

Food

7.1

Crew

8.5

Reviews

1 / 20
6.0
Good

Hannah,Aug 2025

SFO - SAN

Ticket said TSA pre check, but then the TSA agent said that Alaska Airlines has not actually entered the pre check information for the ticket, so I had to use regular security. During boarding, I have a disability and need to board early. The Alaska Airlines employee announced disability boarding, but then immediately announced 2 other groups to board, so I still had to fight the crowds. On the plane, the stewardess was brusk and rude. Seats were very uncomfortable, especially on lower back.
United Airlines
7.4
Good
8,931 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Overall

8.0

Comfort

7.8

Entertainment

7.0

Boarding

8.1

Food

7.1

Crew

8.5

Reviews

1 / 20
6.0
Good

Hannah,Aug 2025

SFO - SAN

Ticket said TSA pre check, but then the TSA agent said that Alaska Airlines has not actually entered the pre check information for the ticket, so I had to use regular security. During boarding, I have a disability and need to board early. The Alaska Airlines employee announced disability boarding, but then immediately announced 2 other groups to board, so I still had to fight the crowds. On the plane, the stewardess was brusk and rude. Seats were very uncomfortable, especially on lower back.
American Airlines
7.2
Good
10,000 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Overall

8.0

Comfort

7.8

Entertainment

7.0

Boarding

8.1

Food

7.1

Crew

8.5

Reviews

1 / 20
6.0
Good

Hannah,Aug 2025

SFO - SAN

Ticket said TSA pre check, but then the TSA agent said that Alaska Airlines has not actually entered the pre check information for the ticket, so I had to use regular security. During boarding, I have a disability and need to board early. The Alaska Airlines employee announced disability boarding, but then immediately announced 2 other groups to board, so I still had to fight the crowds. On the plane, the stewardess was brusk and rude. Seats were very uncomfortable, especially on lower back.

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 05m. Delta provides one of the quickest options available for as low as $482. 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 $421. Other airlines that can offer you cheap pricing are Alaska Airlines, from $423, and American Airlines, from $429. Delta is currently priced 41% below the average price you’ll pay for this route.

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

    $224 is the cheapest one-way deal found within the past few days, from Hawaiian Airlines. You may also be able to find cheap deals on American Airlines and Alaska Airlines, with prices starting from $224 and $229, 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 The Wiltern. Hollywood Bowl, Hollywood Walk of Fame, and The Wiltern are located about 12.5 mi, 11.7 mi, and 10.0 mi, respectively from Los Angeles. Travelers in need of a car in Los Angeles can rent one for about $41 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

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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 septiembre 15, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$421Average$656FlexibilityNo cancel feeOn-timeN/A
Alaska AirlinesCheapest$423Average$658FlexibilityNo cancel feeOn-time75%
American AirlinesCheapest$426Average$726FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$472Average$773FlexibilityNo cancel feeOn-time69%
Hawaiian AirlinesCheapest$535Average$681FlexibilityNo cancel feeOn-time85%
SouthwestCheapest$593Average$705FlexibilityNo cancel feeOn-time63%

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