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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 1/18. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — KOA
Dec 7 — Dec 141
Sat 12/7
Sat 12/14
1 adult, Economy
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The best prices from Chicago to Kona Intl are usually found in September or February, booked 77 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 December 2, 2024.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Popular in

March

Cheapest in

September

Round-trip from

$459
(eDestinos)

One-way from

$190
(Trip.com)
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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High demand for flights, 27% potential price rise
Search Deals
Best time to find cheap flights, 19% potential price drop
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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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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 December 2, 2024.

This Alaska Airlines deal was found by Cheapflights users on 12/1. 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.
Wed 12/111:07 pmORD - KOA
1 stop31h 31mAlaska Airlines
Wed 1/152:00 pmKOA - ORD
2 stops19h 07mAlaska Airlines
Deal found 12/1$569
This Delta deal was found by Cheapflights users on 12/1. 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.
Wed 12/116:05 amORD - KOA
1 stop16h 21mDelta
Wed 1/159:00 pmKOA - ORD
1 stop12h 30mDelta
Deal found 12/1$572
This American Airlines deal was found by Cheapflights users on 12/1. 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.
Wed 12/115:00 amORD - KOA
2 stops14h 41mAmerican Airlines
Wed 1/159:40 pmKOA - ORD
2 stops13h 46mAmerican Airlines
Deal found 12/1$607
This Southwest deal was found by Cheapflights users on 12/1. 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.
Thu 12/126:05 amMDW - KOA
1 stop13h 35mSouthwest
Thu 12/197:30 amKOA - MDW
1 stop10h 15mSouthwest
Deal found 12/1$667
This Delta deal was found by Cheapflights users on 12/1. 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.
Tue 12/39:31 amMDW - KOA
2 stops14h 22mDelta
Wed 12/119:00 pmKOA - MDW
2 stops16h 01mDelta
Deal found 12/1$697
This Southwest deal was found by Cheapflights users on 11/30. 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.
Wed 12/46:15 amORD - KOA
1 stop13h 25mSouthwest
Fri 12/66:10 amKOA - ORD
2 stops12h 55mSouthwest
Deal found 11/30$732
This United Airlines deal was found by Cheapflights users on 12/1. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/153:56 pmORD - KOA
2 stops29h 01mUnited Airlines
Sun 12/224:12 pmKOA - ORD
1 stop11h 14mUnited Airlines
Deal found 12/1$757
This Hawaiian Airlines deal was found by Cheapflights users on 12/1. 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 Hawaiian Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/136:32 amORD - KOA
1 stop14h 06mHawaiian Airlines
Thu 12/262:40 pmKOA - ORD
1 stop10h 50mHawaiian Airlines
Deal found 12/1$767
This Mytrip deal was found by Cheapflights users on 12/1. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/305:04 pmMDW - KOA
3 stops33h 24mWestJet
Sat 1/411:35 pmKOA - MDW
3 stops33h 11mWestJet
Deal found 12/1$2,144

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 2,650,959 searches. Data last updated December 2, 2024.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

ChicagoKailua-Kona

MDW - KOA

MDWKOA

Chicago Midway

Thu 1/16

7:15 am-2:45 pm

2 stops35h 30m

Kona Intl

Thu 1/23

10:21 am-12:54 am

3 stops34h 33m

$459

ChicagoKailua-Kona

ORD - KOA

ORDKOA

Chicago O'Hare Intl

Thu 1/16

7:25 am-2:45 pm

2 stops35h 20m

Kona Intl

Thu 1/23

4:25 pm-12:32 am

2 stops28h 07m

$462

ChicagoKailua-Kona

ORD - KOA

ORDKOA

Chicago O'Hare Intl

Sun 1/12

6:55 pm-2:45 pm

2 stops23h 50m

Kona Intl

Fri 1/17

4:25 pm-4:27 pm

2 stops44h 02m

$492

ChicagoKailua-Kona

ORD - KOA

ORDKOA

Chicago O'Hare Intl

Wed 2/5

7:10 am-5:01 pm

1 stop13h 51m

Kona Intl

Mon 2/10

8:55 pm-1:18 pm

1 stop12h 23m

$507

ChicagoKailua-Kona

ORD - KOA

ORDKOA

Chicago O'Hare Intl

Thu 1/23

6:15 am-6:10 pm

2 stops15h 55m

Kona Intl

Tue 2/4

9:00 pm-1:30 pm

1 stop12h 30m

$543

ChicagoKailua-Kona

ORD - KOA

ORDKOA

Chicago O'Hare Intl

Fri 1/10

9:45 am-7:50 pm

1 stop14h 05m

Kona Intl

Sat 1/18

9:40 pm-12:09 pm

1 stop10h 29m

$572

ChicagoKailua-Kona

MDW - KOA

MDWKOA

Chicago Midway

Wed 2/19

8:35 pm-3:50 pm

2 stops23h 15m

Kona Intl

Mon 2/24

9:00 am-11:00 pm

1 stop10h 00m

$583

ChicagoKailua-Kona

ORD - KOA

ORDKOA

Chicago O'Hare Intl

Fri 4/4

6:00 am-2:25 pm

2 stops13h 25m

Kona Intl

Sun 4/13

8:30 pm-3:20 pm

1 stop13h 50m

$655

ChicagoKailua-Kona

MDW - KOA

MDWKOA

Chicago Midway

Sun 1/26

6:00 am-8:55 pm

2 stops18h 55m

Kona Intl

Fri 1/31

9:30 pm-4:12 pm

2 stops14h 42m

$706

ChicagoKailua-Kona

MDW - KOA

MDWKOA

Chicago Midway

Mon 12/30

5:04 pm-10:28 pm

3 stops33h 24m

Kona Intl

Sat 1/4

11:35 pm-12:46 pm

3 stops33h 11m

$2,144

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/1

Showing 1-10 of 20 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 December.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars
PricelinePrice 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 November 22, 2024.

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 $596). 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 December 2, 2024.

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 morning, which can drop the price by up to 8% versus a flight at noon.

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 1, 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 evenings 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 December 2, 2024.
Peruse reviews from past customers who have flown with Alaska Airlines, Delta and American Airlines 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
4,951 reviews

Overall

8.1

Crew

8.7

Food

7.2

Entertainment

7.7

Boarding

8.2

Comfort

8.1

Reviews

1 / 10

Flight was delayed by one hour and 40 minutes. Also baggage was delivered late at Boston. This delay made me miss my connection from Boston to Hyderabad

Southwest
8.1
Very good
4,951 reviews
Southwest
8.1
Very good
4,951 reviews

Overall

8.1

Crew

8.7

Food

7.2

Entertainment

7.7

Boarding

8.2

Comfort

8.1

Reviews

1 / 10

Flight was delayed by one hour and 40 minutes. Also baggage was delivered late at Boston. This delay made me miss my connection from Boston to Hyderabad

Alaska Airlines
8.0
Very good
9,508 reviews
Southwest
8.1
Very good
4,951 reviews

Overall

8.1

Crew

8.7

Food

7.2

Entertainment

7.7

Boarding

8.2

Comfort

8.1

Reviews

1 / 10

Flight was delayed by one hour and 40 minutes. Also baggage was delivered late at Boston. This delay made me miss my connection from Boston to Hyderabad

Delta
8.0
Very good
8,698 reviews
Southwest
8.1
Very good
4,951 reviews

Overall

8.1

Crew

8.7

Food

7.2

Entertainment

7.7

Boarding

8.2

Comfort

8.1

Reviews

1 / 10

Flight was delayed by one hour and 40 minutes. Also baggage was delivered late at Boston. This delay made me miss my connection from Boston to Hyderabad

Hawaiian Airlines
7.9
Good
2,285 reviews
Southwest
8.1
Very good
4,951 reviews

Overall

8.1

Crew

8.7

Food

7.2

Entertainment

7.7

Boarding

8.2

Comfort

8.1

Reviews

1 / 10

Flight was delayed by one hour and 40 minutes. Also baggage was delivered late at Boston. This delay made me miss my connection from Boston to Hyderabad

United Airlines
7.4
Good
9,141 reviews
Southwest
8.1
Very good
4,951 reviews

Overall

8.1

Crew

8.7

Food

7.2

Entertainment

7.7

Boarding

8.2

Comfort

8.1

Reviews

1 / 10

Flight was delayed by one hour and 40 minutes. Also baggage was delivered late at Boston. This delay made me miss my connection from Boston to Hyderabad

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 $492. Other airlines that can offer you cheap pricing are United Airlines, from $507, and Delta, from $552. Alaska Airlines is currently priced 29% below the average price you’ll pay for this route.

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

    $239 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 $286 and $311, 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 $971, our data indicates the cheapest price to be $597. The most popular route (Chicago O'Hare Intl - Kona Intl), is priced around $462.

  • 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 $596). 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.

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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 2,650,959 searches. Data last updated December 2, 2024.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$364Average$640FlexibilityNo cancel feeOn-timeN/A
Alaska AirlinesCheapest$399Average$650FlexibilityNo cancel feeOn-time75%
American AirlinesCheapest$410Average$647FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$471Average$763FlexibilityNo cancel feeOn-time69%
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