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$224+ 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 10/15. Fares are subject to change and may not be available on all flights or dates of travel.
KOA — CHI
Oct 11 — Oct 181
Sat 10/11
Sat 10/18
1 adult, Economy
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Cheap 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 September 11, 2025.

Round-trip from

$436
(KAYAK)

One-way from

$224
(Alaska Airlines)

Popular in

March

Cheapest in

October

Average price

$471
From Kona Intl to Chicago (CHI)
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One-way flight from Kona Intl to Chicago (CHI)
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Highest demand for flights based on searches. 24% potential increase in price ($239 potential increase over avg. RT price).
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Cheapest flight prices on average. 8% potential price decrease ($56 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Find 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 September 11, 2025.

This KAYAK deal was found by Cheapflights users on 9/10. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/2311:57 amKOA - ORD
1 stop12h 04mAlaska Airlines
Mon 10/278:00 amORD - KOA
2 stops17h 27mAlaska Airlines
Deal found 9/10$436
This United Airlines deal was found by Cheapflights users on 9/10. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/11:05 pmKOA - ORD
1 stop12h 05mUnited Airlines
Tue 10/76:15 amORD - KOA
1 stop10h 41mUnited Airlines
Deal found 9/10$447
This Delta deal was found by Cheapflights users on 9/10. 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.
Wed 10/19:30 pmKOA - ORD
1 stop10h 50mDelta
Tue 10/77:37 amORD - KOA
2 stops16h 46mDelta
Deal found 9/10$468
This Delta deal was found by Cheapflights users on 9/8. 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 9/308:44 pmKOA - ORD
2 stops22h 12mDelta
Mon 10/67:37 amORD - KOA
1 stop14h 53mDelta
Deal found 9/8$481
This Delta deal was found by Cheapflights users on 9/8. 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.
Wed 10/19:30 pmKOA - ORD
1 stop10h 50mDelta
Mon 10/67:37 amORD - KOA
2 stops16h 46mDelta
Deal found 9/8$491
This United Airlines deal was found by Cheapflights users on 9/10. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/251:40 pmKOA - ORD
1 stop11h 18mUnited Airlines
Mon 9/297:10 amORD - KOA
1 stop13h 36mUnited Airlines
Deal found 9/10$501
This Alaska Airlines deal was found by Cheapflights users on 9/8. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/28:00 amKOA - ORD
1 stop11h 03mAlaska Airlines
Tue 10/78:20 amORD - KOA
2 stops18h 20mAlaska Airlines
Deal found 9/8$504
This Alaska Airlines deal was found by Cheapflights users on 9/8. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/308:00 amKOA - ORD
1 stop11h 03mAlaska Airlines
Tue 10/76:00 amORD - KOA
1 stop20h 40mAlaska Airlines
Deal found 9/8$507
This Southwest deal was found by Cheapflights users on 9/10. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/238:30 pmKOA - MDW
1 stop11h 20mSouthwest
Mon 10/275:40 amMDW - KOA
1 stop12h 20mSouthwest
Deal found 9/10$515
This Delta deal was found by Cheapflights users on 9/8. 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 10/29:30 pmKOA - ORD
1 stop10h 50mDelta
Tue 10/77:37 amORD - KOA
1 stop14h 53mDelta
Deal found 9/8$515
This Delta deal was found by Cheapflights users on 9/8. 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.
Fri 10/38:44 pmKOA - ORD
2 stops13h 29mDelta
Wed 10/87:37 amORD - KOA
2 stops16h 46mDelta
Deal found 9/8$516
This Delta deal was found by Cheapflights users on 9/10. 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.
Thu 9/1811:46 amKOA - MDW
2 stops15h 54mDelta
Tue 9/309:35 amMDW - KOA
2 stops13h 00mDelta
Deal found 9/10$761

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 September 11, 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 10/23

11:57 am-5:01 am

1 stop12h 04m

Chicago O'Hare Intl

Mon 10/27

8:00 am-8:27 pm

2 stops17h 27m

$436

Kailua-KonaChicago

KOA - ORD

KOAORD

Kona Intl

Thu 10/2

9:30 pm-1:20 pm

1 stop10h 50m

Chicago O'Hare Intl

Mon 10/6

7:37 am-5:30 pm

1 stop14h 53m

$447

Kailua-KonaChicago

KOA - ORD

KOAORD

Kona Intl

Thu 10/23

9:45 pm-3:59 pm

1 stop13h 14m

Chicago O'Hare Intl

Mon 10/27

6:03 am-1:58 pm

1 stop12h 55m

$447

Kailua-KonaChicago

KOA - ORD

KOAORD

Kona Intl

Wed 10/1

1:05 pm-6:10 am

1 stop12h 05m

Chicago O'Hare Intl

Tue 10/7

6:15 am-11:56 am

1 stop10h 41m

$447

Kailua-KonaChicago

KOA - ORD

KOAORD

Kona Intl

Tue 9/30

9:30 pm-1:20 pm

1 stop10h 50m

Chicago O'Hare Intl

Mon 10/6

7:37 am-5:30 pm

1 stop14h 53m

$447

Kailua-KonaChicago

KOA - ORD

KOAORD

Kona Intl

Wed 10/1

9:30 pm-1:20 pm

1 stop10h 50m

Chicago O'Hare Intl

Wed 10/8

7:37 am-7:23 pm

2 stops16h 46m

$481

Kailua-KonaChicago

KOA - ORD

KOAORD

Kona Intl

Wed 10/1

9:30 pm-1:20 pm

1 stop10h 50m

Chicago O'Hare Intl

Mon 10/6

7:37 am-7:23 pm

2 stops16h 46m

$491

Kailua-KonaChicago

KOA - ORD

KOAORD

Kona Intl

Thu 9/25

1:40 pm-5:58 am

1 stop11h 18m

Chicago O'Hare Intl

Mon 9/29

7:10 am-3:46 pm

1 stop13h 36m

$501

Kailua-KonaChicago

KOA - MDW

KOAMDW

Kona Intl

Thu 10/23

8:30 pm-12:50 pm

1 stop11h 20m

Chicago Midway

Mon 10/27

5:40 am-1:00 pm

1 stop12h 20m

$515

Kailua-KonaChicago

KOA - MDW

KOAMDW

Kona Intl

Thu 9/18

12:47 pm-8:40 am

2 stops14h 53m

Chicago Midway

Tue 9/30

9:35 am-5:35 pm

2 stops13h 00m

$761

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/11

Showing 1-10 of 23 results
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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, August is the cheapest month in which you can book a flight from Kailua-Kona to Chicago (average of $245). Flying from Kailua-Kona to Chicago in March is currently the most expensive (average of $321). 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 September 11, 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 58% on airfare.

How much does it cost to fly round-trip from Kailua-Kona to Chicago?

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. 3 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 $447, Alaska Airlines can have you in Chicago from Kailua-Kona in 10h 50m. 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 $429, 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. Search Cheapflights for deals from Alaska Airlines and American Airlines - these airlines can fly you to your destination from $458 and $545, respectively. United Airlines is currently priced 40% 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 $224. However, be on the lookout for offers from Hawaiian Airlines and Southwest, as they are both options that can get you from Kailua-Kona to Chicago for a low price.

  • 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, August is the cheapest month in which you can book a flight from Kailua-Kona to Chicago (average of $245). Flying from Kailua-Kona to Chicago in March is currently the most expensive (average of $321). 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
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Hammond
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Porter
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Top 3 airlines flying from Kailua-Kona to Chicago

Discover the top 3 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 September 11, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$429Average$635FlexibilityNo cancel feeOn-time69%
Alaska AirlinesCheapest$458Average$631FlexibilityNo cancel feeOn-time75%
American AirlinesCheapest$545Average$726FlexibilityNo cancel feeOn-time71%

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