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$221+ 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 4/21. Fares are subject to change and may not be available on all flights or dates of travel.
KOA — CHI
Apr 23 — Apr 301
Thu 4/23
Thu 4/30
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 March 24, 2026.

This Orbitz 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/2010:39 am
KOA
-
ORD
1 stop22h 42m
Alaska Airlines
Mon 4/277:59 pm
ORD
-
KOA
1 stop23h 57m
Alaska Airlines
Deal found 3/23$557
This Expedia 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/221:16 pm
KOA
-
ORD
1 stop18h 57m
Alaska Airlines
Wed 4/298:00 am
ORD
-
KOA
1 stop16h 52m
Alaska Airlines
Deal found 3/21$558
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/228:25 pm
KOA
-
MDW
1 stop11h 45m
Southwest
Wed 4/296:10 am
MDW
-
KOA
2 stops13h 05m
Southwest
Deal found 3/21$564
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/228:25 pm
KOA
-
ORD
1 stop12h 30m
Southwest
Wed 4/296:15 am
ORD
-
KOA
2 stops16h 50m
Southwest
Deal found 3/21$564
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/208:25 pm
KOA
-
ORD
1 stop12h 30m
Southwest
Mon 4/276:15 am
ORD
-
KOA
2 stops13h 15m
Southwest
Deal found 3/23$565
This Expedia 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/231:16 pm
KOA
-
ORD
1 stop18h 57m
Alaska Airlines
Thu 4/308:00 am
ORD
-
KOA
1 stop16h 52m
Alaska Airlines
Deal found 3/24$580
This Alaska Airlines deal was found by Cheapflights users on 3/19. 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.
Mon 4/271:16 pm
KOA
-
ORD
1 stop18h 57m
Alaska Airlines
Tue 4/285:52 pm
ORD
-
KOA
1 stop31h 00m
Alaska Airlines
Deal found 3/19$602
This Alaska Airlines deal was found by Cheapflights users on 3/19. 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.
Mon 4/278:33 am
KOA
-
ORD
2 stops17h 07m
Multiple Airlines
Tue 4/288:50 am
ORD
-
KOA
2 stops16h 36m
Multiple Airlines
Deal found 3/19$609
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 4/288:00 am
KOA
-
ORD
1 stop17h 40m
Alaska Airlines
Wed 4/298:48 pm
ORD
-
KOA
1 stop28h 04m
Alaska Airlines
Deal found 3/23$668
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/910:00 am
KOA
-
MDW
1 stop14h 45m
Southwest
Mon 4/135:10 am
MDW
-
KOA
2 stops14h 20m
Southwest
Deal found 3/23$774
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/58:25 pm
KOA
-
MDW
1 stop13h 35m
Southwest
Thu 4/910:10 am
MDW
-
KOA
2 stops16h 15m
Southwest
Deal found 3/20$805
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/610:50 am
KOA
-
MDW
2 stops13h 20m
Southwest
Sat 6/138:35 pm
MDW
-
KOA
1 stop18h 00m
Southwest
Deal found 3/23$830

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 March 24, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$557
(Orbitz)

One-way from

$221
(American Airlines)

Popular in

May

Cheapest in

February

Good round-trip deal

$778 or less

Good one-way deal

$437 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. 15% potential increase in price ($115 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease ($27 potential savings vs. average RT price).
Search Deals
Price to beat on a round-trip flight from Kona Intl to Chicago (CHI).
Search Deals
Price to beat on a one-way 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 March 24, 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 - MDW

KOAMDW

Kona Intl

Wed 4/22

8:25 pm-1:10 pm

1 stop11h 45m

Chicago Midway

Wed 4/29

6:10 am-2:15 pm

2 stops13h 05m

$564

Kailua-KonaChicago

KOA - ORD

KOAORD

Kona Intl

Thu 4/23

8:25 pm-3:00 pm

2 stops13h 35m

Chicago O'Hare Intl

Thu 4/30

6:15 am-6:05 pm

2 stops16h 50m

$569

Kailua-KonaChicago

KOA - ORD

KOAORD

Kona Intl

Mon 4/27

1:16 pm-1:13 pm

1 stop18h 57m

Chicago O'Hare Intl

Tue 4/28

5:52 pm-7:52 pm

1 stop31h 00m

$602

Kailua-KonaChicago

KOA - ORD

KOAORD

Kona Intl

Mon 4/27

8:33 am-6:40 am

2 stops17h 07m

Chicago O'Hare Intl

Tue 4/28

8:50 am-8:26 pm

2 stops16h 36m

$609

Kailua-KonaChicago

KOA - ORD

KOAORD

Kona Intl

Tue 4/28

8:00 am-6:40 am

1 stop17h 40m

Chicago O'Hare Intl

Wed 4/29

8:48 pm-7:52 pm

1 stop28h 04m

$668

Kailua-KonaChicago

KOA - ORD

KOAORD

Kona Intl

Tue 4/28

12:55 pm-5:15 am

1 stop11h 20m

Chicago O'Hare Intl

Wed 4/29

8:40 am-7:42 pm

2 stops16h 02m

$688

Kailua-KonaChicago

KOA - ORD

KOAORD

Kona Intl

Tue 4/7

1:22 pm-7:18 am

1 stop12h 56m

Chicago O'Hare Intl

Sun 4/12

7:04 am-2:26 pm

1 stop12h 22m

$697

Kailua-KonaChicago

KOA - ORD

KOAORD

Kona Intl

Tue 4/28

10:30 am-6:40 am

2 stops15h 10m

Chicago O'Hare Intl

Wed 4/29

8:48 pm-7:52 pm

1 stop28h 04m

$698

Kailua-KonaChicago

KOA - MDW

KOAMDW

Kona Intl

Sun 4/5

8:25 pm-3:00 pm

1 stop13h 35m

Chicago Midway

Thu 4/9

10:10 am-9:25 pm

2 stops16h 15m

$805

Kailua-KonaChicago

KOA - MDW

KOAMDW

Kona Intl

Sat 6/6

10:50 am-5:10 am

2 stops13h 20m

Chicago Midway

Sat 6/13

8:35 pm-9:35 am

1 stop18h 00m

$830

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/19

Showing 1-10 of 32 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 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 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, January is the cheapest month in which you can book a flight from Kailua-Kona to Chicago (average of $335). Flying from Kailua-Kona to Chicago in June is currently the most expensive (average of $705). 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 KOA to CHI?

Find hourly flight availability from Kailua-Kona to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated March 24, 2026.

When flying from Kailua-Kona to Chicago, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

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 $564, Southwest can have you in Chicago from Kailua-Kona in 11h 45m. The distance between Kailua-Kona and Chicago is about 4213 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 27% 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 Southwest, 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 $564 on average, our data indicates $915 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, January is the cheapest month in which you can book a flight from Kailua-Kona to Chicago (average of $335). Flying from Kailua-Kona to Chicago in June is currently the most expensive (average of $705). 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
Lansing
Merrillville
Hammond
Porter
Benton Harbor

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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 March 24, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$447Average$841FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$447Average$792FlexibilityNo cancel feeOn-time69%

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