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$219+ 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 9/10. Fares are subject to change and may not be available on all flights or dates of travel.
KOA — CHI
Jun 17 — Jun 241
Tue 6/17
Tue 6/24
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 June 12, 2025.

Round-trip from

$621
(Alaska Airlines)

One-way from

$219
(American Airlines)

Popular in

March

Cheapest in

September

Average price

$658
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. 23% potential increase in price ($230 potential increase over avg. RT price).
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Cheapest flight prices on average. 8% potential price decrease ($55 potential savings vs. average RT price).
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Average for round-trip flights in June 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 June 12, 2025.

This Alaska Airlines deal was found by Cheapflights users on 6/11. 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 7/308:00 amKOA - ORD
1 stop10h 59mAlaska Airlines
Wed 8/67:18 pmORD - KOA
1 stop19h 12mAlaska Airlines
Deal found 6/11$621
This American Airlines deal was found by Cheapflights users on 6/10. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/299:45 pmKOA - ORD
1 stop18h 13mAmerican Airlines
Wed 8/66:00 amORD - KOA
1 stop12h 29mAmerican Airlines
Deal found 6/10$681
This Delta deal was found by Cheapflights users on 6/10. 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 6/119:05 pmKOA - ORD
1 stop11h 18mDelta
Mon 6/167:09 amORD - KOA
1 stop15h 24mDelta
Deal found 6/10$683
This Hawaiian Airlines deal was found by Cheapflights users on 6/11. 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.
Fri 6/138:00 amKOA - ORD
1 stop10h 59mHawaiian Airlines
Tue 7/221:03 pmORD - KOA
1 stop14h 01mHawaiian Airlines
Deal found 6/11$702
This United Airlines deal was found by Cheapflights users on 6/12. 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.
Fri 6/2710:15 pmKOA - ORD
1 stop19h 44mUnited Airlines
Tue 7/13:54 pmORD - KOA
1 stop24h 37mUnited Airlines
Deal found 6/12$833
This Delta deal was found by Cheapflights users on 6/11. 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 6/118:25 pmKOA - MDW
2 stops16h 15mDelta
Mon 6/169:24 amMDW - KOA
2 stops14h 35mDelta
Deal found 6/11$934

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 June 12, 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

Wed 7/30

8:00 am-11:59 pm

1 stop10h 59m

Chicago O'Hare Intl

Wed 8/6

7:18 pm-9:30 am

1 stop19h 12m

$621

Kailua-KonaChicago

KOA - ORD

KOAORD

Kona Intl

Tue 7/29

9:45 pm-8:58 pm

1 stop18h 13m

Chicago O'Hare Intl

Wed 8/6

6:00 am-1:29 pm

1 stop12h 29m

$681

Kailua-KonaChicago

KOA - ORD

KOAORD

Kona Intl

Wed 6/25

9:40 pm-1:23 pm

1 stop10h 43m

Chicago O'Hare Intl

Sun 6/29

7:09 am-5:33 pm

1 stop15h 24m

$687

Kailua-KonaChicago

KOA - ORD

KOAORD

Kona Intl

Fri 6/27

10:15 pm-10:59 pm

1 stop19h 44m

Chicago O'Hare Intl

Tue 7/1

3:54 pm-11:31 am

1 stop24h 37m

$833

Kailua-KonaChicago

KOA - MDW

KOAMDW

Kona Intl

Fri 8/8

8:35 pm-5:10 pm

2 stops15h 35m

Chicago Midway

Fri 8/22

9:15 am-7:00 pm

2 stops14h 45m

$944

Kailua-KonaChicago

KOA - ORD

KOAORD

Kona Intl

Wed 9/10

9:55 pm-3:58 pm

1 stop13h 03m

$219

Kailua-KonaChicago

KOA - ORD

KOAORD

Kona Intl

Thu 10/2

9:32 pm-5:00 am

2 stops26h 28m

$263

Kailua-KonaChicago

KOA - ORD

KOAORD

Kona Intl

Sat 9/6

8:00 am-11:59 pm

1 stop10h 59m

$269

Kailua-KonaChicago

KOA - MDW

KOAMDW

Kona Intl

Thu 10/2

8:30 pm-12:55 pm

1 stop11h 25m

$285

Kailua-KonaChicago

KOA - ORD

KOAORD

Kona Intl

Wed 9/10

7:00 pm-2:25 pm

2 stops14h 25m

$290

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/12

Showing 1-10 of 13 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 June 12, 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.

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 June 12, 2025.
Alaska Airlines
8.0
Very good
10,000 reviews

Entertainment

7.1

Crew

8.5

Overall

8.0

Comfort

7.8

Boarding

8.1

Food

7.1

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Alaska Airlines
8.0
Very good
10,000 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Entertainment

7.1

Crew

8.5

Overall

8.0

Comfort

7.8

Boarding

8.1

Food

7.1

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Southwest
8.0
Very good
4,287 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Entertainment

7.1

Crew

8.5

Overall

8.0

Comfort

7.8

Boarding

8.1

Food

7.1

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Delta
8.0
Very good
7,950 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Entertainment

7.1

Crew

8.5

Overall

8.0

Comfort

7.8

Boarding

8.1

Food

7.1

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Hawaiian Airlines
7.9
Good
2,494 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Entertainment

7.1

Crew

8.5

Overall

8.0

Comfort

7.8

Boarding

8.1

Food

7.1

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
United Airlines
7.4
Good
8,790 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Entertainment

7.1

Crew

8.5

Overall

8.0

Comfort

7.8

Boarding

8.1

Food

7.1

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.

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 $621, Alaska Airlines will fly you from Kailua-Kona to Chicago and back. In addition to Alaska Airlines, many other airlines offer competitively priced options for your trip. Search Cheapflights for deals from American Airlines and Delta - these airlines can fly you to your destination from $681 and $687, respectively. Alaska Airlines is currently priced 14% 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 American Airlines, with whom users have recently found tickets for as low as $219. However, be on the lookout for offers from Alaska Airlines and Hawaiian Airlines, 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 Kailua-Kona?

Book flights to Kailua-Kona if you plan to visit one of these locations
Merrillville
Lansing
Benton Harbor
Porter
Hammond
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 June 12, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$223Average$603FlexibilityNo cancel feeOn-timeN/A
Alaska AirlinesCheapest$418Average$600FlexibilityNo cancel feeOn-time75%
American AirlinesCheapest$419Average$623FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$429Average$760FlexibilityNo cancel feeOn-time69%

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