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$211+ 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 1/23. Fares are subject to change and may not be available on all flights or dates of travel.
KOA — CHI
Jan 17 — Jan 241
Sat 1/17
Sat 1/24
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 December 18, 2025.

This American Airlines deal was found by Cheapflights users on 12/16. 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 12/316:30 pmKOA - ORD
1 stop11h 14mAmerican Airlines
Sun 1/48:15 amORD - KOA
1 stop12h 23mAmerican Airlines
Deal found 12/16$712
This Delta deal was found by Cheapflights users on 12/16. 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 12/3110:55 pmKOA - ORD
2 stops18h 41mDelta
Sun 1/47:25 amORD - KOA
1 stop12h 23mDelta
Deal found 12/16$717
This American Airlines deal was found by Cheapflights users on 12/16. 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.
Fri 12/266:30 pmKOA - ORD
1 stop10h 10mAmerican Airlines
Sun 12/286:00 amORD - KOA
1 stop12h 54mAmerican Airlines
Deal found 12/16$948
This American Airlines deal was found by Cheapflights users on 12/16. 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 12/2410:09 pmKOA - ORD
1 stop15h 43mAmerican Airlines
Mon 12/295:21 amORD - KOA
1 stop13h 55mAmerican Airlines
Deal found 12/16$969
This United Airlines deal was found by Cheapflights users on 12/16. 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.
Wed 12/2411:20 pmKOA - ORD
1 stop25h 17mUnited Airlines
Mon 12/299:15 pmORD - KOA
2 stops19h 36mUnited Airlines
Deal found 12/16$977
This Southwest deal was found by Cheapflights users on 12/16. 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 12/243:40 pmKOA - ORD
2 stops17h 50mSouthwest
Mon 12/297:15 amORD - KOA
2 stops14h 55mSouthwest
Deal found 12/16$984
This Southwest deal was found by Cheapflights users on 12/16. 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 12/249:15 pmKOA - MDW
1 stop12h 25mSouthwest
Mon 12/295:10 amMDW - KOA
1 stop12h 30mSouthwest
Deal found 12/16$1,023
This Southwest deal was found by Cheapflights users on 12/16. 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 12/269:15 pmKOA - ORD
2 stops12h 50mSouthwest
Sun 12/287:15 amORD - KOA
2 stops14h 55mSouthwest
Deal found 12/16$1,044
This Delta deal was found by Cheapflights users on 12/16. 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 12/3110:55 pmKOA - MDW
2 stops14h 24mDelta
Sun 1/49:29 amMDW - KOA
2 stops14h 06mDelta
Deal found 12/16$1,204
This Alaska Airlines deal was found by Cheapflights users on 12/16. 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 12/312:25 pmKOA - ORD
1 stop20h 12mAlaska Airlines
Wed 1/78:00 amORD - KOA
1 stop12h 55mAlaska Airlines
Deal found 12/16$2,267
This Alaska Airlines deal was found by Cheapflights users on 12/16. 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 12/316:16 pmKOA - ORD
2 stops16h 25mMultiple Airlines
Wed 1/78:00 amORD - KOA
1 stop12h 55mMultiple Airlines
Deal found 12/16$2,399

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 December 18, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$393
(Alaska Airlines)

One-way from

$211
(American Airlines)

Popular in

March

Cheapest in

December

Average price

$424

Good one-way deal

$516 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)
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One-way flight from Kona Intl to Chicago (CHI)
Search Deals
Highest demand for flights based on searches. 18% potential increase in price ($160 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 7% potential price decrease ($48 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
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 December 18, 2025.
Use the filters below to find and compare flights from Kailua-Kona to Chicago that are best for you.

Fly from

Kailua-Kona

Fly to

Chicago

Route

Depart

Return

Price

Kailua-KonaChicago

KOA - ORD

KOAORD

Kona Intl

Thu 1/15

2:51 pm-11:37 pm

1 stop28h 46m

Chicago O'Hare Intl

Thu 1/22

3:44 pm-3:57 pm

1 stop28h 13m

$393

Kailua-KonaChicago

KOA - ORD

KOAORD

Kona Intl

Thu 1/15

2:51 pm-2:29 pm

1 stop19h 38m

Chicago O'Hare Intl

Thu 1/22

9:00 am-9:30 pm

2 stops16h 30m

$399

Kailua-KonaChicago

KOA - ORD

KOAORD

Kona Intl

Wed 1/14

2:51 pm-2:29 pm

1 stop19h 38m

Chicago O'Hare Intl

Sun 1/18

3:44 pm-3:57 pm

1 stop28h 13m

$413

Kailua-KonaChicago

KOA - ORD

KOAORD

Kona Intl

Sat 1/24

2:24 pm-11:37 pm

1 stop29h 13m

Chicago O'Hare Intl

Sat 1/31

3:44 pm-3:57 pm

1 stop28h 13m

$432

Kailua-KonaChicago

KOA - ORD

KOAORD

Kona Intl

Wed 1/14

6:00 am-11:50 pm

2 stops13h 50m

Chicago O'Hare Intl

Sun 1/18

3:44 pm-3:57 pm

1 stop28h 13m

$447

Kailua-KonaChicago

KOA - ORD

KOAORD

Kona Intl

Sat 1/24

2:24 pm-2:29 pm

1 stop20h 05m

Chicago O'Hare Intl

Sat 1/31

9:00 am-7:18 am

2 stops26h 18m

$461

Kailua-KonaChicago

KOA - ORD

KOAORD

Kona Intl

Wed 2/18

1:10 pm-11:59 pm

1 stop30h 49m

Chicago O'Hare Intl

Sun 2/22

3:07 pm-3:53 pm

1 stop28h 46m

$488

Kailua-KonaChicago

KOA - ORD

KOAORD

Kona Intl

Wed 2/18

1:10 pm-11:59 pm

1 stop30h 49m

Chicago O'Hare Intl

Sun 2/22

8:20 am-8:13 am

2 stops27h 53m

$537

Kailua-KonaChicago

KOA - MDW

KOAMDW

Kona Intl

Wed 12/31

10:55 pm-5:19 pm

2 stops14h 24m

Chicago Midway

Sun 1/4

9:29 am-7:35 pm

2 stops14h 06m

$1,204

Kailua-KonaChicago

KOA - MDW

KOAMDW

Kona Intl

Thu 1/1

9:55 pm-5:19 pm

2 stops15h 24m

Chicago Midway

Mon 1/5

6:45 am-9:30 pm

2 stops18h 45m

$1,434

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/17

Showing 1-10 of 29 results
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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 December.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star

*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 eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Kailua-Kona-Chicago flight deals on Cheapflights vs. eDreams >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 eDreams the most. eDreams 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, October is the cheapest month in which you can book a flight from Kailua-Kona to Chicago (average of $447). Flying from Kailua-Kona to Chicago in April is currently the most expensive (average of $752). 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 December 18, 2025.

One of the essential ways to save on airfare from Kailua-Kona to Chicago is to remain as flexible as possible. Flights that are in the afternoon tend to be the most expensive. A flight in the morning could potentially save you up to 67% on airfare.

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 $1,204, Alaska Airlines can have you in Chicago from Kailua-Kona in 14h 24m. 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, United Airlines will fly you from Kailua-Kona to Chicago and back. In addition to United Airlines, many other airlines offer competitively priced options for your trip. Check Cheapflights for deals on American Airlines for as low as $545. United Airlines is currently priced 35% 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 American Airlines and Delta, 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 $362. While the most popular route (Kona Intl - Chicago O'Hare Intl) can be booked for $426 on average, our data indicates $632 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, October is the cheapest month in which you can book a flight from Kailua-Kona to Chicago (average of $447). Flying from Kailua-Kona to Chicago in April is currently the most expensive (average of $752). 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 December 18, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$447Average$792FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$545Average$653FlexibilityNo cancel feeOn-time71%

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