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Kailua-Kona

$297+ 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 2/3. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — KOA
Feb 4 — Feb 111
Tue 2/4
Tue 2/11
1 adult, Economy
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The best prices from Chicago to Kona Intl are usually found in September or April, 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 January 30, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$551
(Delta)

One-way from

$297
(Alaska Airlines)

Popular in

December

Cheapest in

September

Average price

$622
Provider with most accurate pricing for Chicago (CHI)-Kona Intl flight deals.
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Provider most trusted by Cheapflights users for Chicago (CHI)-Kona Intl flights.
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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. 4% potential increase in price ($36 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($25 potential savings vs. average RT price).
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Average for round-trip flights in January 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 January 30, 2025.

This Delta deal was found by Cheapflights users on 1/30. 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 5/156:00 amORD - KOA
2 stops17h 39mDelta
Tue 5/209:45 pmKOA - ORD
1 stop10h 46mDelta
Deal found 1/30$552
This Alaska Airlines deal was found by Cheapflights users on 1/30. 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 3/47:45 amORD - KOA
1 stop19h 48mAlaska Airlines
Tue 3/1110:09 amKOA - ORD
2 stops21h 55mAlaska Airlines
Deal found 1/30$554
This American Airlines deal was found by Cheapflights users on 1/30. 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 3/49:50 amORD - KOA
1 stop14h 22mAmerican Airlines
Tue 3/119:10 pmKOA - ORD
1 stop10h 04mAmerican Airlines
Deal found 1/30$564
This Mytrip deal was found by Cheapflights users on 1/30. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/146:00 amORD - KOA
3 stops29h 25mMultiple Airlines
Mon 5/192:55 pmKOA - ORD
2 stops21h 18mMultiple Airlines
Deal found 1/30$582
This Southwest deal was found by Cheapflights users on 1/30. 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 3/48:35 pmMDW - KOA
2 stops24h 15mSouthwest
Tue 3/117:50 amKOA - MDW
1 stop11h 00mSouthwest
Deal found 1/30$589
This Delta deal was found by Cheapflights users on 1/30. 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 4/2410:15 amMDW - KOA
2 stops13h 24mDelta
Sat 5/38:30 pmKOA - MDW
2 stops12h 52mDelta
Deal found 1/30$594
This Southwest deal was found by Cheapflights users on 1/30. 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.
Fri 1/315:45 amORD - KOA
1 stop14h 05mSouthwest
Fri 2/79:00 amKOA - ORD
2 stops21h 20mSouthwest
Deal found 1/30$647
This United Airlines deal was found by Cheapflights users on 1/30. 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.
Sat 3/17:37 pmORD - KOA
2 stops21h 16mUnited Airlines
Sun 3/910:55 pmKOA - ORD
2 stops20h 28mUnited Airlines
Deal found 1/30$664
This Hawaiian Airlines deal was found by Cheapflights users on 1/29. 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.
Wed 2/122:07 pmORD - KOA
1 stop13h 37mHawaiian Airlines
Sat 2/159:00 amKOA - ORD
1 stop10h 59mHawaiian Airlines
Deal found 1/29$803

Find flights from Chicago to Kailua-Kona within your budget

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 January 30, 2025.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

ChicagoKailua-Kona

ORD - KOA

ORDKOA

Chicago O'Hare Intl

Fri 5/2

7:00 am-6:39 pm

2 stops16h 39m

Kona Intl

Wed 5/7

9:45 pm-6:01 pm

2 stops15h 16m

$550

ChicagoKailua-Kona

ORD - KOA

ORDKOA

Chicago O'Hare Intl

Fri 2/28

7:45 am-11:33 pm

1 stop19h 48m

Kona Intl

Sun 3/9

10:02 pm-11:59 pm

1 stop20h 57m

$573

ChicagoKailua-Kona

ORD - KOA

ORDKOA

Chicago O'Hare Intl

Tue 2/18

8:05 am-8:12 pm

2 stops16h 07m

Kona Intl

Tue 3/4

9:45 pm-3:23 pm

2 stops13h 38m

$575

ChicagoKailua-Kona

MDW - KOA

MDWKOA

Chicago Midway

Tue 3/4

8:35 pm-4:50 pm

2 stops24h 15m

Kona Intl

Tue 3/11

7:50 am-11:50 pm

1 stop11h 00m

$589

ChicagoKailua-Kona

MDW - KOA

MDWKOA

Chicago Midway

Thu 4/24

10:15 am-6:39 pm

2 stops13h 24m

Kona Intl

Sat 5/3

8:30 pm-2:22 pm

2 stops12h 52m

$594

ChicagoKailua-Kona

ORD - KOA

ORDKOA

Chicago O'Hare Intl

Sun 5/4

6:15 am-12:55 pm

1 stop11h 40m

Kona Intl

Thu 5/15

8:30 pm-4:45 pm

2 stops15h 15m

$606

ChicagoKailua-Kona

ORD - KOA

ORDKOA

Chicago O'Hare Intl

Sun 2/23

6:10 pm-12:53 pm

2 stops22h 43m

Kona Intl

Sat 3/1

11:10 pm-4:52 am

1 stop25h 42m

$796

ChicagoKailua-Kona

ORD - KOA

ORDKOA

Chicago O'Hare Intl

Wed 2/12

2:07 pm-11:44 pm

1 stop13h 37m

Kona Intl

Sat 2/15

9:00 am-11:59 pm

1 stop10h 59m

$803

ChicagoKailua-Kona

ORD - KOA

ORDKOA

Chicago O'Hare Intl

Tue 2/4

7:45 am-4:25 pm

1 stop12h 40m

$297

ChicagoKailua-Kona

ORD - KOA

ORDKOA

Chicago O'Hare Intl

Sat 3/8

8:13 am-8:38 pm

1 stop16h 25m

$316

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/28

Showing 1-10 of 14 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 January.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars
CheapfaremartPrice Accuracy-Trust Score*3 stars
PricelinePrice Accuracy1 starTrust Score*3 stars
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 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.

Travel insights for flights from Chicago to Kailua-Kona

Get recent, data-driven insights about flights from Chicago to Kailua-Kona including ideal travel times, pricing trends, and more.

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 January 24, 2025.

Booking 64 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 $618). 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 January 30, 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 January 30, 2025.
Peruse reviews from past customers who have flown with Southwest, Alaska Airlines 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.
Southwest
8.1
Very good
4,585 reviews

Food

7.1

Boarding

8.2

Overall

8.1

Crew

8.7

Comfort

8.1

Entertainment

7.7

Reviews

1 / 20

6.0
Good

Lauren,Dec 2024

MCI - DCA

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Southwest
8.1
Very good
4,585 reviews
Southwest
8.1
Very good
4,585 reviews

Food

7.1

Boarding

8.2

Overall

8.1

Crew

8.7

Comfort

8.1

Entertainment

7.7

Reviews

1 / 20

6.0
Good

Lauren,Dec 2024

MCI - DCA

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Alaska Airlines
8.0
Very good
9,688 reviews
Southwest
8.1
Very good
4,585 reviews

Food

7.1

Boarding

8.2

Overall

8.1

Crew

8.7

Comfort

8.1

Entertainment

7.7

Reviews

1 / 20

6.0
Good

Lauren,Dec 2024

MCI - DCA

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Delta
8.0
Very good
8,454 reviews
Southwest
8.1
Very good
4,585 reviews

Food

7.1

Boarding

8.2

Overall

8.1

Crew

8.7

Comfort

8.1

Entertainment

7.7

Reviews

1 / 20

6.0
Good

Lauren,Dec 2024

MCI - DCA

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Hawaiian Airlines
7.9
Good
2,320 reviews
Southwest
8.1
Very good
4,585 reviews

Food

7.1

Boarding

8.2

Overall

8.1

Crew

8.7

Comfort

8.1

Entertainment

7.7

Reviews

1 / 20

6.0
Good

Lauren,Dec 2024

MCI - DCA

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

United Airlines
7.4
Good
8,913 reviews
Southwest
8.1
Very good
4,585 reviews

Food

7.1

Boarding

8.2

Overall

8.1

Crew

8.7

Comfort

8.1

Entertainment

7.7

Reviews

1 / 20

6.0
Good

Lauren,Dec 2024

MCI - DCA

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

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. 4 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 $551. Other airlines that can offer you cheap pricing are Alaska Airlines, from $573, and American Airlines, from $575. 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?

    $297 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 Southwest, with prices starting from $316 and $318, 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 $37 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 $618). 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 4 airlines flying from Chicago to Kailua-Kona

Discover the top 4 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 January 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$350Average$641FlexibilityNo cancel feeOn-timeN/A
Alaska AirlinesCheapest$414Average$648FlexibilityNo cancel feeOn-time75%
American AirlinesCheapest$416Average$680FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$473Average$758FlexibilityNo cancel feeOn-time69%
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