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$247+ Cheap flights from Kailua-Kona (KOA) to Chicago (CHI)

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 8/18. Fares are subject to change and may not be available on all flights or dates of travel.
KOA — CHI
Jun 9 — Jun 161
Tue 6/9
Tue 6/16
1 adult, Economy
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Cheap flight deals from Kailua-Kona to Chicago

Cheapest flights from Kailua-Kona to Chicago
Explore the most affordable flight options available from Kailua-Kona to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on May 10, 2026.

This Alaska Airlines deal was found by Cheapflights users on 5/5. 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.
Thu 9/246:00 am
KOA
-
ORD
2 stops12h 57m
Multiple Airlines
Mon 9/286:01 am
ORD
-
KOA
1 stop13h 50m
Multiple Airlines
Deal found 5/5$500
This Alaska Airlines deal was found by Cheapflights users on 5/5. 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.
Thu 9/2412:35 pm
KOA
-
ORD
1 stop12h 47m
Alaska Airlines
Mon 9/286:01 am
ORD
-
KOA
1 stop13h 50m
Alaska Airlines
Deal found 5/5$524
This Alaska Airlines deal was found by Cheapflights users on 5/7. 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 9/112:49 pm
KOA
-
ORD
1 stop12h 33m
Multiple Airlines
Wed 9/29:00 am
ORD
-
KOA
2 stops15h 32m
Multiple Airlines
Deal found 5/7$599
This United Airlines deal was found by Cheapflights users on 5/8. 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.
Mon 6/81:52 pm
KOA
-
ORD
1 stop10h 06m
United Airlines
Thu 6/256:00 am
ORD
-
KOA
1 stop10h 42m
United Airlines
Deal found 5/8$607
This Delta deal was found by Cheapflights users on 5/8. 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 5/289:55 pm
KOA
-
ORD
2 stops16h 25m
Delta
Tue 6/28:42 am
ORD
-
KOA
2 stops15h 38m
Delta
Deal found 5/8$612
This United Airlines deal was found by Cheapflights users on 5/8. 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.
Thu 5/281:52 pm
KOA
-
ORD
1 stop10h 06m
United Airlines
Tue 6/26:00 am
ORD
-
KOA
1 stop10h 42m
United Airlines
Deal found 5/8$633
This Delta deal was found by Cheapflights users on 5/8. 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 6/238:50 pm
KOA
-
ORD
1 stop14h 55m
Delta
Tue 7/77:35 am
ORD
-
KOA
1 stop16h 42m
Delta
Deal found 5/8$656
This Delta deal was found by Cheapflights users on 5/7. 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.
Fri 5/228:50 pm
KOA
-
MDW
2 stops16h 43m
Delta
Sun 5/249:22 am
MDW
-
KOA
2 stops14h 58m
Delta
Deal found 5/7$745
This Southwest deal was found by Cheapflights users on 5/8. 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 6/2210:00 am
KOA
-
MDW
1 stop14h 45m
Southwest
Sun 7/55:00 am
MDW
-
KOA
1 stop12h 45m
Southwest
Deal found 5/8$790
This Delta deal was found by Cheapflights users on 5/8. 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 6/239:37 pm
KOA
-
MDW
2 stops19h 40m
Delta
Tue 7/79:49 am
MDW
-
KOA
2 stops14h 28m
Delta
Deal found 5/8$806
This Southwest deal was found by Cheapflights users on 5/9. 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 6/510:00 am
KOA
-
MDW
1 stop14h 45m
Southwest
Thu 6/116:30 am
MDW
-
KOA
1 stop11h 15m
Southwest
Deal found 5/9$811
This Delta deal was found by Cheapflights users on 5/10. 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 7/149:16 pm
KOA
-
MDW
2 stops16h 09m
Delta
Tue 7/289:19 am
MDW
-
KOA
2 stops14h 58m
Delta
Deal found 5/10$815

Find flight deals from Kailua-Kona to Chicago

Discover tips and strategies to find the most affordable flight options for your journey from Kailua-Kona (KOA) to Chicago (CHI). 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 May 10, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$599
(Alaska Airlines)

One-way from

$247
(Delta)

Popular in

July

Cheapest in

February

Good round-trip deal

$778 or less
Provider with most accurate pricing for Kona Intl-Chicago (CHI) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Kona Intl-Chicago (CHI) flights.
Search Deals
From Kona Intl to Chicago (CHI)
Search Deals
One-way flight from Kona Intl to Chicago (CHI)
Search Deals
Highest demand for flights based on searches. 12% potential increase in price ($86 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($14 potential savings vs. average RT price).
Search Deals
Price to beat on a round-trip flight from Kona Intl to Chicago (CHI).
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Kailua-Kona to Chicago 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 May 10, 2026.
Use the filters below to find and compare flights from Kailua-Kona to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

Kailua-KonaChicago

KOA - ORD

KOAORD

Kona Intl

Thu 9/24

12:35 pm-6:22 am

1 stop12h 47m

Chicago O'Hare Intl

Mon 9/28

6:01 am-2:51 pm

1 stop13h 50m

$524

Kailua-KonaChicago

KOA - ORD

KOAORD

Kona Intl

Thu 9/24

6:00 am-11:57 pm

2 stops12h 57m

Chicago O'Hare Intl

Mon 9/28

9:00 am-6:17 pm

2 stops14h 17m

$580

Kailua-KonaChicago

KOA - ORD

KOAORD

Kona Intl

Tue 9/1

12:49 pm-6:22 am

1 stop12h 33m

Chicago O'Hare Intl

Wed 9/2

9:00 am-7:32 pm

2 stops15h 32m

$599
Quickest round-trip

Kailua-KonaChicago

KOA - ORD

KOAORD

Kona Intl

Mon 6/8

1:52 pm-4:58 am

1 stop10h 06m

Chicago O'Hare Intl

Thu 6/25

6:00 am-11:42 am

1 stop10h 42m

$607

Kailua-KonaChicago

KOA - ORD

KOAORD

Kona Intl

Fri 6/5

1:52 pm-5:53 am

1 stop11h 01m

Chicago O'Hare Intl

Thu 6/11

12:45 pm-7:31 pm

1 stop11h 46m

$660

Kailua-KonaChicago

KOA - ORD

KOAORD

Kona Intl

Tue 6/30

8:50 pm-6:58 pm

2 stops17h 08m

Chicago O'Hare Intl

Wed 7/8

6:30 am-7:17 pm

2 stops17h 47m

$668

Kailua-KonaChicago

KOA - ORD

KOAORD

Kona Intl

Tue 7/14

9:16 pm-6:57 pm

2 stops16h 41m

Chicago O'Hare Intl

Tue 7/28

6:55 am-5:35 pm

1 stop15h 40m

$680

Kailua-KonaChicago

KOA - ORD

KOAORD

Kona Intl

Thu 7/16

9:16 pm-6:57 pm

2 stops16h 41m

Chicago O'Hare Intl

Tue 7/28

6:55 am-5:35 pm

1 stop15h 40m

$690

Kailua-KonaChicago

KOA - MDW

KOAMDW

Kona Intl

Fri 5/22

8:50 pm-6:33 pm

2 stops16h 43m

Chicago Midway

Sun 5/24

9:22 am-7:20 pm

2 stops14h 58m

$745

Kailua-KonaChicago

KOA - MDW

KOAMDW

Kona Intl

Fri 6/5

10:00 am-5:45 am

1 stop14h 45m

Chicago Midway

Thu 6/11

6:30 am-12:45 pm

1 stop11h 15m

$811

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/5

Showing 1-10 of 33 resultsSorted by cheapest first
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Compare providers for flights from Kailua-Kona to Chicago

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 Kailua-Kona to Chicago in May.
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 Kailua-Kona-Chicago flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Kailua-Kona-Chicago flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Kailua-Kona-Chicago flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Kailua-Kona-Chicago 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 Kailua-Kona-Chicago 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 Kailua-Kona to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from Kailua-Kona 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 Kailua-Kona to Chicago

What is the cheapest month to book a flight from Kailua-Kona to Chicago?

Currently, June is the cheapest month in which you can book a flight from Kailua-Kona to Chicago (average of $311). Flying from Kailua-Kona to Chicago in May is currently the most expensive (average of $762). 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.

Related info for your journey

Find useful and relevant information for your journey from Kailua-Kona to Chicago. 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 from for flights from Kailua-Kona to Chicago?

    For a flight from Kailua-Kona to Chicago, you will be flying from Kona Intl. Kona Intl (KOA) is just 7.7 mi from the center of the city. Kona Intl is the only Kailua-Kona airport and it handles 0 outbound flights to Chicago per day. 2 airlines have flights to Chicago from Kona Intl on a regular basis.

  • How long is the flight from Kailua-Kona to Chicago?

    For as low as $607, Alaska Airlines can have you in Chicago from Kailua-Kona in 10h 06m. The distance between Kailua-Kona and Chicago 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 Kailua-Kona to Chicago round-trip?

    Currently priced at $447, American Airlines will fly you from Kailua-Kona to Chicago and back. In addition to American Airlines, many other airlines offer competitively priced options for your trip. Check Cheapflights for deals on United Airlines for as low as $447. American Airlines is currently priced 23% below the average price you’ll pay for this route.

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

    The cheapest airline one-way is Alaska Airlines, with whom users have recently found tickets for as low as $223. However, be on the lookout for offers from Delta and American Airlines, as they are both options that can get you from Kailua-Kona to Chicago for a low price.

  • What are the cheapest flights from Kailua-Kona to Chicago?

    Looking at all options, your cheapest flight can be booked for $334. While the most popular route (Kona Intl - Chicago O'Hare Intl) can be booked for $604 on average, our data indicates $1,394 when flying from Kailua-Kona to Chicago.

  • Can I find deals for flights from Kailua-Kona to Chicago that include hotel bookings?

    Yes. In addition to deals on Kailua-Kona to Chicago flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Kailua-Kona to Chicago?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Kailua-Kona to Chicago.

  • Can I find deals for business class flights from Kailua-Kona to Chicago?

    Yes. Cheapflights offers flight deals from Kailua-Kona to Chicago 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 Kailua-Kona to Chicago?

    Currently, June is the cheapest month in which you can book a flight from Kailua-Kona to Chicago (average of $311). Flying from Kailua-Kona to Chicago in May is currently the most expensive (average of $762). 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

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Benton Harbor
Lansing
Merrillville
Hammond
Porter

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Top 2 airlines flying from Kailua-Kona to Chicago

Discover the top 2 airlines that operate flights from Kailua-Kona to Chicago. 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 May 10, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$447Average$757FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$447Average$718FlexibilityNo cancel feeOn-time69%

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