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Kailua-Kona

$235+ 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 4/20. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — KOA
Apr 24 — May 11
Fri 4/24
Fri 5/1
1 adult, Economy
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Cheap 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 March 25, 2026.

This Alaska Airlines deal was found by Cheapflights users on 3/23. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/283:52 pm
ORD
-
KOA
2 stops24h 05m
Multiple Airlines
Wed 5/63:56 pm
KOA
-
ORD
2 stops26h 47m
Multiple Airlines
Deal found 3/23$508
This Alaska Airlines deal was found by Cheapflights users on 3/24. 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 5/63:52 pm
ORD
-
KOA
2 stops22h 44m
Alaska Airlines
Mon 5/111:16 pm
KOA
-
ORD
1 stop24h 47m
Alaska Airlines
Deal found 3/24$512
This Kiwi.com deal was found by Cheapflights users on 3/21. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/58:50 am
ORD
-
KOA
2 stops29h 45m
Alaska Airlines
Tue 5/121:16 pm
KOA
-
ORD
1 stop24h 34m
Alaska Airlines
Deal found 3/21$529
This American Airlines deal was found by Cheapflights users on 3/23. 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.
Mon 4/137:04 am
ORD
-
KOA
1 stop12h 22m
American Airlines
Wed 4/221:22 pm
KOA
-
ORD
1 stop11h 25m
American Airlines
Deal found 3/23$530
This American Airlines deal was found by Cheapflights users on 3/21. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/57:04 am
ORD
-
KOA
1 stop12h 22m
American Airlines
Tue 5/121:22 pm
KOA
-
ORD
1 stop12h 56m
American Airlines
Deal found 3/21$533
This Orbitz deal was found by Cheapflights users on 3/20. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/53:52 pm
ORD
-
KOA
2 stops24h 05m
Multiple Airlines
Tue 5/198:00 am
KOA
-
ORD
1 stop10h 59m
Multiple Airlines
Deal found 3/20$539
This Expedia deal was found by Cheapflights users on 3/23. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/293:52 pm
ORD
-
KOA
2 stops22h 44m
Alaska Airlines
Wed 5/61:16 pm
KOA
-
ORD
1 stop18h 57m
Alaska Airlines
Deal found 3/23$546
This Delta deal was found by Cheapflights users on 3/25. 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 4/305:15 am
ORD
-
KOA
2 stops17h 28m
Delta
Mon 5/48:50 pm
KOA
-
ORD
1 stop11h 33m
Delta
Deal found 3/25$550
This Kiwi.com deal was found by Cheapflights users on 3/24. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/278:50 am
ORD
-
KOA
2 stops15h 26m
Multiple Airlines
Wed 4/291:16 pm
KOA
-
ORD
1 stop18h 57m
Multiple Airlines
Deal found 3/24$551
This Southwest deal was found by Cheapflights users on 3/22. 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.
Mon 8/176:40 am
MDW
-
KOA
1 stop11h 00m
Southwest
Wed 8/2610:00 am
KOA
-
MDW
1 stop14h 45m
Southwest
Deal found 3/22$554
This Alaska Airlines deal was found by Cheapflights users on 3/20. 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 8/256:00 am
ORD
-
KOA
1 stop12h 42m
Alaska Airlines
Thu 8/278:00 am
KOA
-
ORD
1 stop10h 59m
Alaska Airlines
Deal found 3/20$554
This Alaska Airlines deal was found by Cheapflights users on 3/23. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/216:00 am
ORD
-
KOA
1 stop12h 39m
Alaska Airlines
Wed 4/221:16 pm
KOA
-
ORD
1 stop29h 27m
Alaska Airlines
Deal found 3/23$555

Find 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 March 25, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$508
(Alaska Airlines)

One-way from

$235
(WAYA)

Popular in

December

Cheapest in

January

Average price

$892
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. 5% potential increase in price ($44 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($28 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in March 2026
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 March 25, 2026.
Use the filters below to find and compare flights from Chicago to Kailua-Kona that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoKailua-Kona

ORD - KOA

ORDKOA

Chicago O'Hare Intl

Tue 4/21

6:00 am-1:39 pm

1 stop12h 39m

Kona Intl

Wed 4/22

1:16 pm-11:43 pm

1 stop29h 27m

$555

ChicagoKailua-Kona

ORD - KOA

ORDKOA

Chicago O'Hare Intl

Mon 5/4

3:52 pm-2:56 pm

1 stop28h 04m

Kona Intl

Mon 5/11

1:16 pm-1:13 pm

1 stop18h 57m

$558

ChicagoKailua-Kona

MDW - KOA

MDWKOA

Chicago Midway

Fri 5/8

10:10 am-9:25 pm

2 stops16h 15m

Kona Intl

Thu 5/14

10:00 am-5:45 am

1 stop14h 45m

$566

ChicagoKailua-Kona

ORD - KOA

ORDKOA

Chicago O'Hare Intl

Thu 4/30

8:00 am-7:52 pm

1 stop16h 52m

Kona Intl

Mon 5/4

1:16 pm-1:13 pm

1 stop18h 57m

$580

ChicagoKailua-Kona

MDW - KOA

MDWKOA

Chicago Midway

Sun 4/19

5:45 am-1:15 pm

1 stop12h 30m

Kona Intl

Sun 4/26

7:00 pm-1:45 pm

2 stops13h 45m

$596

ChicagoKailua-Kona

ORD - KOA

ORDKOA

Chicago O'Hare Intl

Tue 4/21

8:20 am-6:26 am

2 stops27h 06m

Kona Intl

Wed 4/22

7:46 pm-4:56 pm

2 stops16h 10m

$607

ChicagoKailua-Kona

ORD - KOA

ORDKOA

Chicago O'Hare Intl

Mon 5/4

6:15 am-6:05 pm

2 stops16h 50m

Kona Intl

Mon 5/11

8:25 pm-6:50 pm

2 stops17h 25m

$613

ChicagoKailua-Kona

ORD - KOA

ORDKOA

Chicago O'Hare Intl

Fri 4/17

2:09 pm-10:59 am

1 stop25h 50m

Kona Intl

Fri 4/24

1:16 pm-1:13 pm

1 stop18h 57m

$618
Quickest round-trip

ChicagoKailua-Kona

MDW - KOA

MDWKOA

Chicago Midway

Fri 4/17

5:10 am-1:15 pm

1 stop13h 05m

Kona Intl

Fri 4/24

7:00 pm-12:15 pm

2 stops12h 15m

$624

ChicagoKailua-Kona

ORD - KOA

ORDKOA

Chicago O'Hare Intl

Mon 5/4

7:59 pm-3:21 pm

2 stops24h 22m

Kona Intl

Mon 5/11

1:16 pm-1:13 pm

1 stop18h 57m

$628

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/22

Showing 1-10 of 28 resultsSorted by cheapest first
1
2
3

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 March.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust 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.

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 March 13, 2026.

Booking 61 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, March is the cheapest month in which you can book a flight from Chicago to Kailua-Kona (average of $371). Flying from Chicago to Kailua-Kona in July is currently the most expensive (average of $668). 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 March 25, 2026.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Chicago to Kailua-Kona as you normally would.

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 March 25, 2026.
Get a feel of what it's like to fly with Southwest,Alaska Airlines, andDelta 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.
Southwest
8.0
Very good
4,332 reviews

Crew

8.6

Food

7.0

Overall

8.0

Comfort

8.0

Entertainment

7.5

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
Southwest
8.0
Very good
4,332 reviews
Southwest
8.0
Very good
4,332 reviews

Crew

8.6

Food

7.0

Overall

8.0

Comfort

8.0

Entertainment

7.5

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
Alaska Airlines
7.9
Good
12,108 reviews
Southwest
8.0
Very good
4,332 reviews

Crew

8.6

Food

7.0

Overall

8.0

Comfort

8.0

Entertainment

7.5

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
Delta
7.9
Good
8,327 reviews
Southwest
8.0
Very good
4,332 reviews

Crew

8.6

Food

7.0

Overall

8.0

Comfort

8.0

Entertainment

7.5

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
United Airlines
7.4
Good
9,477 reviews
Southwest
8.0
Very good
4,332 reviews

Crew

8.6

Food

7.0

Overall

8.0

Comfort

8.0

Entertainment

7.5

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
American Airlines
7.1
Good
11,494 reviews
Southwest
8.0
Very good
4,332 reviews

Crew

8.6

Food

7.0

Overall

8.0

Comfort

8.0

Entertainment

7.5

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.

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 12h 39m. Alaska Airlines provides one of the quickest options available for as low as $555. The distance from Chicago to Kailua-Kona is about 4205 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 $350. Other airlines that can offer you cheap pricing are Alaska Airlines, from $418, and Hawaiian Airlines, from $429. Delta is currently priced 50% below the average price you’ll pay for this route.

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

    $195 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 United Airlines, with prices starting from $233 and $382, 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 12.4 mi, 11.7 mi, and 10.9 mi, respectively from Los Angeles. Travelers in need of a car in Los Angeles can rent one for about $44 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, March is the cheapest month in which you can book a flight from Chicago to Kailua-Kona (average of $371). Flying from Chicago to Kailua-Kona in July is currently the most expensive (average of $668). 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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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 March 25, 2026.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$350Average$639FlexibilityNo cancel feeOn-timeN/A
Alaska AirlinesCheapest$418Average$667FlexibilityNo cancel feeOn-time75%
Hawaiian AirlinesCheapest$429Average$571FlexibilityNo cancel feeOn-time85%
SouthwestCheapest$442Average$807FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$447Average$706FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$447Average$852FlexibilityNo cancel feeOn-time69%

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