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$285+ 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 3/9. Fares are subject to change and may not be available on all flights or dates of travel.
KOA — CHI
Feb 27 — Mar 61
Thu 2/27
Thu 3/6
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 February 22, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$449
(Delta)

One-way from

$285
(Delta)

Popular in

March

Cheapest in

August

Average price

$509

Good one-way deal

$324 or less
Provider with most accurate pricing for Kona Intl-Chicago (CHI) flight deals.
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Provider most trusted by Cheapflights users for Kona Intl-Chicago (CHI) flights.
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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. 13% potential increase in price ($103 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 9% potential price decrease ($57 potential savings vs. average RT price).
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Average for round-trip flights in February 2025
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Price to beat on a one-way flight from Kona Intl to Chicago (CHI).
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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 February 22, 2025.

This Delta deal was found by Cheapflights users on 2/21. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/229:30 pmKOA - ORD
2 stops15h 00mDelta
Wed 4/307:50 amORD - KOA
1 stop14h 49mDelta
Deal found 2/21$449
This Alaska Airlines deal was found by Cheapflights users on 2/21. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/229:33 pmKOA - ORD
1 stop27h 32mAlaska Airlines
Wed 4/306:00 amORD - KOA
1 stop21h 11mAlaska Airlines
Deal found 2/21$521
This Hawaiian Airlines deal was found by Cheapflights users on 2/21. 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 Hawaiian Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/208:00 amKOA - ORD
1 stop10h 59mHawaiian Airlines
Tue 6/36:00 amORD - KOA
1 stop12h 34mHawaiian Airlines
Deal found 2/21$636
This Southwest deal was found by Cheapflights users on 2/21. 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.
Sun 5/1110:00 amKOA - MDW
2 stops14h 20mSouthwest
Sat 5/179:25 pmMDW - KOA
2 stops22h 00mSouthwest
Deal found 2/21$676
This American Airlines deal was found by Cheapflights users on 2/21. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/211:47 pmKOA - ORD
1 stop11h 06mAmerican Airlines
Tue 6/35:38 pmORD - KOA
1 stop23h 39mAmerican Airlines
Deal found 2/21$692
This Southwest deal was found by Cheapflights users on 2/20. 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.
Fri 2/2810:00 amKOA - ORD
2 stops20h 00mSouthwest
Fri 3/76:00 amORD - KOA
2 stops16h 25mSouthwest
Deal found 2/20$708
This Delta deal was found by Cheapflights users on 2/21. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/229:30 pmKOA - MDW
2 stops15h 50mDelta
Wed 4/3010:20 amMDW - KOA
2 stops13h 22mDelta
Deal found 2/21$744
This United Airlines deal was found by Cheapflights users on 2/21. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/85:25 pmKOA - ORD
Nonstop7h 55mUnited Airlines
Wed 3/128:48 amORD - KOA
1 stop16h 06mUnited Airlines
Deal found 2/21$1,044

Find flights from Kailua-Kona to Chicago within your budget

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 February 22, 2025.

Fly from

Kailua-Kona

Fly to

Chicago

Route

Depart

Return

Price

Kailua-KonaChicago

KOA - ORD

KOAORD

Kona Intl

Tue 4/22

9:30 pm-5:30 pm

2 stops15h 00m

Chicago O'Hare Intl

Wed 4/30

7:50 am-5:39 pm

1 stop14h 49m

$449

Kailua-KonaChicago

KOA - ORD

KOAORD

Kona Intl

Tue 4/22

9:33 pm-6:05 am

1 stop27h 32m

Chicago O'Hare Intl

Wed 4/30

6:00 am-10:11 pm

1 stop21h 11m

$521

Kailua-KonaChicago

KOA - ORD

KOAORD

Kona Intl

Tue 5/20

8:00 am-11:59 pm

1 stop10h 59m

Chicago O'Hare Intl

Tue 6/3

6:00 am-1:34 pm

1 stop12h 34m

$636

Kailua-KonaChicago

KOA - MDW

KOAMDW

Kona Intl

Sun 5/11

10:00 am-5:20 am

2 stops14h 20m

Chicago Midway

Sat 5/17

9:25 pm-2:25 pm

2 stops22h 00m

$676

Kailua-KonaChicago

KOA - ORD

KOAORD

Kona Intl

Wed 5/21

1:47 pm-5:53 am

1 stop11h 06m

Chicago O'Hare Intl

Tue 6/3

5:38 pm-12:17 pm

1 stop23h 39m

$692

Kailua-KonaChicago

KOA - MDW

KOAMDW

Kona Intl

Tue 4/22

9:30 pm-6:20 pm

2 stops15h 50m

Chicago Midway

Wed 4/30

10:20 am-6:42 pm

2 stops13h 22m

$744

Kailua-KonaChicago

KOA - ORD

KOAORD

Kona Intl

Sat 3/8

5:25 pm-5:20 am

Nonstop7h 55m

Chicago O'Hare Intl

Wed 3/12

8:48 am-7:54 pm

1 stop16h 06m

$1,044

Kailua-KonaChicago

KOA - ORD

KOAORD

Kona Intl

Sun 3/9

9:30 pm-9:47 pm

2 stops19h 17m

$285

Kailua-KonaChicago

KOA - ORD

KOAORD

Kona Intl

Fri 5/9

2:15 pm-9:59 pm

2 stops26h 44m

$296

Kailua-KonaChicago

KOA - ORD

KOAORD

Kona Intl

Wed 4/2

9:40 pm-5:23 pm

1 stop14h 43m

$310

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/21

Showing 1-10 of 13 results
1
2

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 February.
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.

Travel insights for flights from Kailua-Kona to Chicago

Get recent, data-driven insights about flights from Kailua-Kona to Chicago including ideal travel times, pricing trends, and more.

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 February 22, 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 52% on airfare.

Rainfall in Chicago by month

Plan your trip to Chicago by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Chicago ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago when rainfall is around 1.7 in.

Temperature in Chicago by month

Plan your trip to Chicago by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Chicago, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

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 February 22, 2025.
See what other customers who have flown with Southwest, Alaska Airlines and Delta 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.
Southwest
8.1
Very good
4,395 reviews

Entertainment

7.6

Crew

8.7

Boarding

8.2

Overall

8.1

Comfort

8.1

Food

7.1

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Southwest
8.1
Very good
4,395 reviews
Southwest
8.1
Very good
4,395 reviews

Entertainment

7.6

Crew

8.7

Boarding

8.2

Overall

8.1

Comfort

8.1

Food

7.1

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Alaska Airlines
8.0
Very good
9,700 reviews
Southwest
8.1
Very good
4,395 reviews

Entertainment

7.6

Crew

8.7

Boarding

8.2

Overall

8.1

Comfort

8.1

Food

7.1

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Delta
8.0
Very good
8,212 reviews
Southwest
8.1
Very good
4,395 reviews

Entertainment

7.6

Crew

8.7

Boarding

8.2

Overall

8.1

Comfort

8.1

Food

7.1

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Hawaiian Airlines
7.9
Good
2,314 reviews
Southwest
8.1
Very good
4,395 reviews

Entertainment

7.6

Crew

8.7

Boarding

8.2

Overall

8.1

Comfort

8.1

Food

7.1

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

United Airlines
7.4
Good
8,759 reviews
Southwest
8.1
Very good
4,395 reviews

Entertainment

7.6

Crew

8.7

Boarding

8.2

Overall

8.1

Comfort

8.1

Food

7.1

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

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. 4 airlines have flights to Chicago from Kona Intl on a regular basis.

  • What are the cheapest airlines flying from Kailua-Kona to Chicago round-trip?

    Currently priced at $449, Delta will fly you from Kailua-Kona to Chicago and back. In addition to Delta, many other airlines offer competitively priced options for your trip. Search Cheapflights for deals from Alaska Airlines and Hawaiian Airlines - these airlines can fly you to your destination from $521 and $636, respectively. Delta is currently priced 31% 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 Delta, with whom users have recently found tickets for as low as $285. However, be on the lookout for offers from Alaska Airlines 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 $324. While the most popular route (Kona Intl - Chicago O'Hare Intl) can be booked for $449 on average our data indicates $324 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, 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 Kailua-Kona?

Book flights to Kailua-Kona if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Benton Harbor
Porter
Lansing
Valparaiso
Chesterton

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Top 4 airlines flying from Kailua-Kona to Chicago

Discover the top 4 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 February 22, 2025.
AirlineCheapestAverageFlexibilityOn-time
Alaska AirlinesCheapest$220Average$574FlexibilityNo cancel feeOn-time75%
DeltaCheapest$222Average$491FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$392Average$677FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$399Average$586FlexibilityNo cancel feeOn-time71%
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