HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Kailua-Kona

$205+ 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 9/6. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — KOA
ago. 5 — ago. 121
mar. 8/5
mar. 8/12
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

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

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

Cheapflights Tip: The best prices from Chicago to Kona Intl are usually found in September or October, booked 88 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 julio 31, 2025.

Round-trip from

$405
(Alaska Airlines)

One-way from

$205
(Alaska Airlines)

Popular in

March

Cheapest in

September

Average price

$733
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. 3% potential increase in price ($25 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($23 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in July 2025
Search Deals

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 julio 31, 2025.

This Alaska Airlines deal was found by Cheapflights users on 7/29. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 11/119:20 amORD - KOA
1 stop33h 23mAlaska Airlines
mar. 11/1812:09 pmKOA - ORD
1 stop21h 45mAlaska Airlines
Deal found 7/29$405
This American Airlines deal was found by Cheapflights users on 7/30. 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.
mié. 10/86:03 amORD - KOA
1 stop12h 55mAmerican Airlines
mié. 10/229:45 pmKOA - ORD
1 stop11h 30mAmerican Airlines
Deal found 7/30$406
This Hawaiian Airlines deal was found by Cheapflights users on 7/31. 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 Hawaiian Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 9/83:20 pmORD - KOA
1 stop11h 49mHawaiian Airlines
vie. 9/1212:16 pmKOA - ORD
1 stop11h 44mHawaiian Airlines
Deal found 7/31$418
This Delta deal was found by Cheapflights users on 7/30. 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.
mar. 9/97:15 amORD - KOA
1 stop15h 19mDelta
jue. 9/189:30 pmKOA - ORD
1 stop14h 45mDelta
Deal found 7/30$423
This Southwest deal was found by Cheapflights users on 7/28. 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. 12/35:15 amMDW - KOA
1 stop12h 25mSouthwest
mié. 12/109:15 pmKOA - MDW
1 stop10h 20mSouthwest
Deal found 7/28$508
This Delta deal was found by Cheapflights users on 7/29. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 11/46:00 amMDW - KOA
2 stops17h 53mDelta
jue. 11/69:30 pmKOA - MDW
2 stops31h 10mDelta
Deal found 7/29$613

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 julio 31, 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

6:03 am-1:58 pm

1 stop12h 55m

Kona Intl

mié. 10/22

9:45 pm-2:15 pm

1 stop11h 30m

$406

ChicagoKailua-Kona

ORD - KOA

ORDKOA

Chicago O'Hare Intl

dom. 8/24

6:20 am-3:51 pm

2 stops14h 31m

Kona Intl

jue. 9/4

12:16 pm-5:00 am

1 stop11h 44m

$414

ChicagoKailua-Kona

ORD - KOA

ORDKOA

Chicago O'Hare Intl

lun. 9/8

3:20 pm-10:09 pm

1 stop11h 49m

Kona Intl

vie. 9/12

12:16 pm-5:00 am

1 stop11h 44m

$418

ChicagoKailua-Kona

ORD - KOA

ORDKOA

Chicago O'Hare Intl

mar. 9/9

7:15 am-5:34 pm

1 stop15h 19m

Kona Intl

jue. 9/18

9:30 pm-5:15 pm

1 stop14h 45m

$423

ChicagoKailua-Kona

MDW - KOA

MDWKOA

Chicago Midway

dom. 8/24

5:30 am-1:05 pm

2 stops12h 35m

Kona Intl

mar. 9/2

8:30 pm-1:15 pm

1 stop11h 45m

$552

ChicagoKailua-Kona

MDW - KOA

MDWKOA

Chicago Midway

mié. 10/29

5:04 pm-7:23 pm

2 stops31h 19m

Kona Intl

jue. 11/6

9:30 pm-8:40 am

2 stops31h 10m

$614

ChicagoKailua-Kona

ORD - KOA

ORDKOA

Chicago O'Hare Intl

sáb. 9/6

5:45 pm-11:16 am

1 stop22h 31m

$205

ChicagoKailua-Kona

ORD - KOA

ORDKOA

Chicago O'Hare Intl

mié. 9/10

6:00 am-1:42 pm

1 stop12h 42m

$212

ChicagoKailua-Kona

ORD - KOA

ORDKOA

Chicago O'Hare Intl

jue. 10/2

7:10 am-5:35 pm

2 stops15h 25m

$297

ChicagoKailua-Kona

MDW - KOA

MDWKOA

Chicago Midway

jue. 9/11

5:15 am-12:10 pm

1 stop11h 55m

$305

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/31

Showing 1-10 of 13 results
1
2

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 July 25, 2025.

Booking 88 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 julio 31, 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.

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 julio 31, 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

Comfort

7.8

Crew

8.5

Food

7.1

Overall

8.0

Boarding

8.1

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

Jonathan,Jul 2025

SEA - BOS

Fantastic Check-in with easy baggage drop. While it took a while to find out which was the gate, the boarding was a dream, the stewards were simply incredible and the flight fantastic.
Alaska Airlines
8.0
Very good
10,000 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Comfort

7.8

Crew

8.5

Food

7.1

Overall

8.0

Boarding

8.1

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

Jonathan,Jul 2025

SEA - BOS

Fantastic Check-in with easy baggage drop. While it took a while to find out which was the gate, the boarding was a dream, the stewards were simply incredible and the flight fantastic.
Southwest
8.0
Very good
4,246 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Comfort

7.8

Crew

8.5

Food

7.1

Overall

8.0

Boarding

8.1

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

Jonathan,Jul 2025

SEA - BOS

Fantastic Check-in with easy baggage drop. While it took a while to find out which was the gate, the boarding was a dream, the stewards were simply incredible and the flight fantastic.
Delta
8.0
Very good
7,981 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Comfort

7.8

Crew

8.5

Food

7.1

Overall

8.0

Boarding

8.1

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

Jonathan,Jul 2025

SEA - BOS

Fantastic Check-in with easy baggage drop. While it took a while to find out which was the gate, the boarding was a dream, the stewards were simply incredible and the flight fantastic.
Hawaiian Airlines
7.8
Good
2,611 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Comfort

7.8

Crew

8.5

Food

7.1

Overall

8.0

Boarding

8.1

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

Jonathan,Jul 2025

SEA - BOS

Fantastic Check-in with easy baggage drop. While it took a while to find out which was the gate, the boarding was a dream, the stewards were simply incredible and the flight fantastic.
United Airlines
7.4
Good
8,900 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Comfort

7.8

Crew

8.5

Food

7.1

Overall

8.0

Boarding

8.1

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

Jonathan,Jul 2025

SEA - BOS

Fantastic Check-in with easy baggage drop. While it took a while to find out which was the gate, the boarding was a dream, the stewards were simply incredible and the flight fantastic.

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.

  • 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 $405. Other airlines that can offer you cheap pricing are American Airlines, from $406, and Hawaiian Airlines, from $418. Alaska Airlines is currently priced 42% below the average price you’ll pay for this route.

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

    $205 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 Delta, with prices starting from $212 and $297, 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 $51 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

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Chicago to Kailua-Kona

See prices for flight routes from nearby airports that may be better suited for you.
O'Hare Intl to Honolulu flights
O'Hare Intl to Kahului flights
Midway to Honolulu flights
O'Hare Intl to Lihue flights
St. Louis to Honolulu flights
O'Hare Intl to Kailua-Kona flights
St. Louis to Kahului flights
Midway to Kahului flights
St. Louis to Lihue flights
O'Hare Intl to Hilo flights
Midway to Lihue flights
St. Louis to Kailua-Kona flights
Midway to Kailua-Kona flights
St. Louis to Hilo flights
Peoria to Honolulu flights
Bloomington to Honolulu flights
Midway to Hilo flights
Moline to Honolulu flights
Peoria to Lihue flights
Peoria to Kahului flights
Decatur to Honolulu flights
Bloomington to Kahului flights
Moline to Kahului flights
Moline to Kailua-Kona flights
Champaign to Honolulu flights
Bloomington to Lihue flights
Evansville to Honolulu flights
Springfield to Kahului flights
Springfield to Honolulu flights
Moline to Lihue flights
Moline to Hilo flights
Evansville to Kahului flights
O'Hare Intl to Waimea (Big Island) flights
O'Hare Intl to Kapalua flights
Evansville to Lihue flights
Dubuque to Honolulu flights
St. Louis to Kapalua flights
Springfield to Lihue flights
O'Hare Intl to Hana flights
St. Louis to Hana flights
Champaign to Kailua-Kona flights
St. Louis to Waimea (Big Island) flights

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 julio 31, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$364Average$589FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$413Average$694FlexibilityNo cancel feeOn-time71%
Alaska AirlinesCheapest$455Average$659FlexibilityNo cancel feeOn-time75%
United AirlinesCheapest$506Average$782FlexibilityNo cancel feeOn-time69%
Hawaiian AirlinesCheapest$535Average$728FlexibilityNo cancel feeOn-time85%
SouthwestCheapest$547Average$705FlexibilityNo cancel feeOn-time63%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.