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$259+ 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 9/15. Fares are subject to change and may not be available on all flights or dates of travel.
KOA — CHI
Aug 7 — Aug 141
Fri 8/7
Fri 8/14
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 July 8, 2026.

This Expedia deal was found by Cheapflights users on 7/7. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/2710:35 am
KOA
-
ORD
1 stop21h 47m
Alaska Airlines
Sun 8/308:17 pm
ORD
-
KOA
1 stop23h 31m
Alaska Airlines
Deal found 7/7$533
This Expedia deal was found by Cheapflights users on 7/7. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/278:45 pm
KOA
-
ORD
2 stops17h 36m
Multiple Airlines
Sun 8/308:17 pm
ORD
-
KOA
1 stop23h 31m
Multiple Airlines
Deal found 7/7$539
This Delta deal was found by Cheapflights users on 7/7. 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.
Thu 8/278:42 pm
KOA
-
ORD
2 stops16h 37m
Delta
Sun 8/306:00 am
ORD
-
KOA
2 stops16h 35m
Delta
Deal found 7/7$545
This Southwest deal was found by Cheapflights users on 7/7. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/2710:00 am
KOA
-
MDW
1 stop14h 45m
Southwest
Sun 8/305:25 am
MDW
-
KOA
1 stop12h 15m
Southwest
Deal found 7/7$569
This Alaska Airlines deal was found by Cheapflights users on 7/6. 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 8/511:58 am
KOA
-
ORD
1 stop12h 02m
Alaska Airlines
Tue 8/118:02 am
ORD
-
KOA
1 stop11h 33m
Alaska Airlines
Deal found 7/6$604
This Expedia deal was found by Cheapflights users on 7/4. 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.
Mon 8/248:00 am
KOA
-
ORD
2 stops17h 20m
Multiple Airlines
Sat 8/292:18 pm
ORD
-
KOA
1 stop29h 30m
Multiple Airlines
Deal found 7/4$609
This Expedia deal was found by Cheapflights users on 7/6. 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 8/59:19 am
KOA
-
ORD
2 stops14h 41m
Multiple Airlines
Tue 8/116:00 am
ORD
-
KOA
1 stop13h 35m
Multiple Airlines
Deal found 7/6$610
This American Airlines deal was found by Cheapflights users on 7/4. 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.
Mon 8/249:45 pm
KOA
-
ORD
1 stop13h 20m
American Airlines
Sat 8/2910:35 pm
ORD
-
KOA
1 stop22h 40m
American Airlines
Deal found 7/4$661
This Alaska Airlines deal was found by Cheapflights users on 7/7. 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.
Wed 10/2111:59 am
KOA
-
ORD
1 stop13h 21m
Alaska Airlines
Fri 10/237:20 am
ORD
-
KOA
1 stop12h 26m
Alaska Airlines
Deal found 7/7$684
This Alaska Airlines deal was found by Cheapflights users on 7/7. 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.
Wed 10/217:15 pm
KOA
-
ORD
2 stops18h 05m
Multiple Airlines
Fri 10/237:20 am
ORD
-
KOA
1 stop12h 26m
Multiple Airlines
Deal found 7/7$686
This Southwest deal was found by Cheapflights users on 7/8. 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.
Wed 8/510:00 am
KOA
-
MDW
2 stops14h 45m
Southwest
Tue 8/116:50 am
MDW
-
KOA
1 stop10h 50m
Southwest
Deal found 7/8$690
This Southwest deal was found by Cheapflights users on 7/4. 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.
Tue 7/288:25 pm
KOA
-
MDW
1 stop12h 00m
Southwest
Wed 8/58:50 pm
MDW
-
KOA
2 stops20h 35m
Southwest
Deal found 7/4$791

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 July 8, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$533
(Expedia)

One-way from

$259
(lol.travel)

Popular in

July

Cheapest in

February

Average price

$951

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. 22% potential increase in price ($177 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 6% potential price decrease ($36 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in July 2026
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 July 8, 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

Thu 8/27

10:00 am-5:45 am

1 stop14h 45m

Chicago Midway

Sun 8/30

5:25 am-12:40 pm

1 stop12h 15m

$569
Quickest round-trip

Kailua-KonaChicago

KOA - ORD

KOAORD

Kona Intl

Wed 8/5

11:58 am-5:00 am

1 stop12h 02m

Chicago O'Hare Intl

Tue 8/11

8:02 am-2:35 pm

1 stop11h 33m

$604

Kailua-KonaChicago

KOA - ORD

KOAORD

Kona Intl

Mon 8/24

8:00 am-6:20 am

2 stops17h 20m

Chicago O'Hare Intl

Sat 8/29

2:18 pm-2:48 pm

1 stop29h 30m

$609

Kailua-KonaChicago

KOA - ORD

KOAORD

Kona Intl

Wed 10/21

11:59 am-6:20 am

1 stop13h 21m

Chicago O'Hare Intl

Fri 10/23

7:20 am-2:46 pm

1 stop12h 26m

$684

Kailua-KonaChicago

KOA - ORD

KOAORD

Kona Intl

Wed 10/21

7:15 pm-6:20 pm

2 stops18h 05m

Chicago O'Hare Intl

Fri 10/23

7:20 am-2:46 pm

1 stop12h 26m

$686

Kailua-KonaChicago

KOA - MDW

KOAMDW

Kona Intl

Wed 8/5

10:00 am-5:45 am

1 stop14h 45m

Chicago Midway

Tue 8/11

6:50 am-12:40 pm

1 stop10h 50m

$715

Kailua-KonaChicago

KOA - MDW

KOAMDW

Kona Intl

Tue 7/28

8:25 pm-1:25 pm

1 stop12h 00m

Chicago Midway

Wed 8/5

8:50 pm-12:25 pm

2 stops20h 35m

$791

Kailua-KonaChicago

KOA - MDW

KOAMDW

Kona Intl

Wed 8/5

10:05 pm-6:33 pm

2 stops15h 28m

Chicago Midway

Tue 8/11

9:59 am-7:17 pm

2 stops14h 18m

$821

Kailua-KonaChicago

KOA - MDW

KOAMDW

Kona Intl

Sun 7/19

10:50 am-5:55 am

1 stop14h 05m

Chicago Midway

Sat 7/25

8:35 pm-9:35 am

1 stop18h 00m

$846
Cheapest one-way

Kailua-KonaChicago

KOA - MDW

KOAMDW

Kona Intl

Thu 12/17

9:00 am-5:45 am

1 stop16h 45m

$337

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/7

Showing 1-10 of 25 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 July.
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 May is currently the most expensive (average of $821). 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.

Reviews of airlines servicing Chicago

Get insights into the airlines that provide service to Chicago. 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 Chicago. Reviews last updated July 8, 2026.
See what other customers who have flown with United Airlines from Kailua-Kona to Chicago have to say. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
United Airlines
7.4
Good
9,948 reviews

Boarding

7.7

Overall

7.4

Entertainment

7.1

Food

6.7

Comfort

7.3

Crew

8.1

Reviews

1 / 20
2.0
Mediocre

Deb,Jan 2025

MKE - ORD

It was terrible! So much to say, but in a nutshell we used vouchers from United because our last trip with them was awful with many mishaps and errors made. Unfortunately, this trip was even worse!
United Airlines
7.4
Good
9,948 reviews
United Airlines
7.4
Good
9,948 reviews

Boarding

7.7

Overall

7.4

Entertainment

7.1

Food

6.7

Comfort

7.3

Crew

8.1

Reviews

1 / 20
2.0
Mediocre

Deb,Jan 2025

MKE - ORD

It was terrible! So much to say, but in a nutshell we used vouchers from United because our last trip with them was awful with many mishaps and errors made. Unfortunately, this trip was even worse!

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 $604, Southwest can have you in Chicago from Kailua-Kona in 12h 02m. 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 $422, 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 32% 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 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 $534 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, 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 May is currently the most expensive (average of $821). 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
Hammond
Lansing
Merrillville
Valparaiso
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 July 8, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$422Average$834FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$447Average$704FlexibilityNo cancel feeOn-time69%

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