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$205+ 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
Aug 4 — Aug 111
Mon 8/4
Mon 8/11
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 July 30, 2025.

Round-trip from

$409
(American Airlines)

One-way from

$205
(Southwest)

Popular in

March

Cheapest in

September

Average price

$746
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 ($237 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 July 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 July 30, 2025.

This American Airlines deal was found by Cheapflights users on 7/29. 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 9/89:55 pmKOA - ORD
1 stop13h 03mAmerican Airlines
Sun 9/146:55 amORD - KOA
1 stop11h 47mAmerican Airlines
Deal found 7/29$409
This Delta deal was found by Cheapflights users on 7/29. 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.
Sun 9/219:30 pmKOA - ORD
1 stop14h 45mDelta
Thu 9/257:10 amORD - KOA
1 stop15h 19mDelta
Deal found 7/29$423
This Alaska Airlines deal was found by Cheapflights users on 7/29. 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 9/98:00 amKOA - ORD
1 stop11h 03mAlaska Airlines
Wed 9/105:45 pmORD - KOA
1 stop22h 31mAlaska Airlines
Deal found 7/29$447
This Kiwi.com deal was found by Cheapflights users on 7/29. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/89:32 pmKOA - ORD
1 stop21h 31mHawaiian Airlines
Sun 9/148:00 amORD - KOA
1 stop13h 44mHawaiian Airlines
Deal found 7/29$460
This Trip.com deal was found by Cheapflights users on 7/29. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/83:19 pmKOA - ORD
1 stop21h 52mMultiple Airlines
Sun 9/147:06 pmORD - KOA
2 stops32h 07mMultiple Airlines
Deal found 7/29$482
This Southwest deal was found by Cheapflights users on 7/29. 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 8/206:05 amKOA - ORD
2 stops12h 35mSouthwest
Mon 9/16:15 amORD - KOA
1 stop10h 55mSouthwest
Deal found 7/29$550
This Southwest deal was found by Cheapflights users on 7/29. 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 9/99:15 amKOA - MDW
2 stops14h 55mSouthwest
Wed 9/108:40 amMDW - KOA
2 stops14h 30mSouthwest
Deal found 7/29$556
This United Airlines deal was found by Cheapflights users on 7/29. 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.
Tue 8/191:15 pmKOA - ORD
1 stop11h 08mUnited Airlines
Tue 8/2610:49 amORD - KOA
1 stop13h 35mUnited Airlines
Deal found 7/29$662
This Delta deal was found by Cheapflights users on 7/30. 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 8/148:41 pmKOA - MDW
2 stops16h 56mDelta
Mon 8/189:15 amMDW - KOA
2 stops14h 45mDelta
Deal found 7/30$1,061

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 30, 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

Mon 9/8

9:55 pm-3:58 pm

1 stop13h 03m

Chicago O'Hare Intl

Sun 9/14

6:55 am-1:42 pm

1 stop11h 47m

$409

Kailua-KonaChicago

KOA - ORD

KOAORD

Kona Intl

Sun 9/21

9:30 pm-5:15 pm

1 stop14h 45m

Chicago O'Hare Intl

Thu 9/25

7:10 am-5:29 pm

1 stop15h 19m

$423

Kailua-KonaChicago

KOA - ORD

KOAORD

Kona Intl

Tue 9/9

8:00 am-12:03 am

1 stop11h 03m

Chicago O'Hare Intl

Wed 9/10

5:45 pm-11:16 am

1 stop22h 31m

$447

Kailua-KonaChicago

KOA - ORD

KOAORD

Kona Intl

Mon 9/8

9:32 pm-12:03 am

1 stop21h 31m

Chicago O'Hare Intl

Sun 9/14

8:00 am-4:44 pm

1 stop13h 44m

$460

Kailua-KonaChicago

KOA - ORD

KOAORD

Kona Intl

Mon 9/8

3:19 pm-6:11 pm

1 stop21h 52m

Chicago O'Hare Intl

Sun 9/14

7:06 pm-10:13 pm

2 stops32h 07m

$482

Kailua-KonaChicago

KOA - ORD

KOAORD

Kona Intl

Wed 8/20

6:05 am-11:40 pm

2 stops12h 35m

Chicago O'Hare Intl

Mon 9/1

6:15 am-12:10 pm

1 stop10h 55m

$550

Kailua-KonaChicago

KOA - MDW

KOAMDW

Kona Intl

Tue 9/9

9:15 am-5:10 am

2 stops14h 55m

Chicago Midway

Wed 9/10

8:40 am-6:10 pm

2 stops14h 30m

$556

Kailua-KonaChicago

KOA - ORD

KOAORD

Kona Intl

Tue 8/19

1:15 pm-5:23 am

1 stop11h 08m

Chicago O'Hare Intl

Tue 8/26

10:49 am-7:24 pm

1 stop13h 35m

$662

Kailua-KonaChicago

KOA - MDW

KOAMDW

Kona Intl

Thu 8/14

8:41 pm-6:37 pm

2 stops16h 56m

Chicago Midway

Mon 8/18

9:15 am-7:00 pm

2 stops14h 45m

$1,061

Kailua-KonaChicago

KOA - MDW

KOAMDW

Kona Intl

Wed 9/10

8:30 pm-11:45 am

1 stop10h 15m

$205

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/30

Showing 1-10 of 17 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 July 30, 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.

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 30, 2025.
See what other customers who have flown with Alaska Airlines, Southwest, 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.
Alaska Airlines
8.0
Very good
10,000 reviews

Overall

8.0

Crew

8.5

Food

7.1

Boarding

8.1

Comfort

7.8

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

Jonathan,Jul 2025

SEA - BOS

Fantastic Check-in with easy baggage drop. While it took a while to find out which was the gate, the boarding was a dream, the stewards were simply incredible and the flight fantastic.
Alaska Airlines
8.0
Very good
10,000 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Overall

8.0

Crew

8.5

Food

7.1

Boarding

8.1

Comfort

7.8

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

Jonathan,Jul 2025

SEA - BOS

Fantastic Check-in with easy baggage drop. While it took a while to find out which was the gate, the boarding was a dream, the stewards were simply incredible and the flight fantastic.
Southwest
8.0
Very good
4,241 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Overall

8.0

Crew

8.5

Food

7.1

Boarding

8.1

Comfort

7.8

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

Jonathan,Jul 2025

SEA - BOS

Fantastic Check-in with easy baggage drop. While it took a while to find out which was the gate, the boarding was a dream, the stewards were simply incredible and the flight fantastic.
Delta
8.0
Very good
7,980 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Overall

8.0

Crew

8.5

Food

7.1

Boarding

8.1

Comfort

7.8

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

Jonathan,Jul 2025

SEA - BOS

Fantastic Check-in with easy baggage drop. While it took a while to find out which was the gate, the boarding was a dream, the stewards were simply incredible and the flight fantastic.
Hawaiian Airlines
7.8
Good
2,611 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Overall

8.0

Crew

8.5

Food

7.1

Boarding

8.1

Comfort

7.8

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

Jonathan,Jul 2025

SEA - BOS

Fantastic Check-in with easy baggage drop. While it took a while to find out which was the gate, the boarding was a dream, the stewards were simply incredible and the flight fantastic.
United Airlines
7.4
Good
8,896 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Overall

8.0

Crew

8.5

Food

7.1

Boarding

8.1

Comfort

7.8

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

Jonathan,Jul 2025

SEA - BOS

Fantastic Check-in with easy baggage drop. While it took a while to find out which was the gate, the boarding was a dream, the stewards were simply incredible and the flight fantastic.

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.

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

    Currently priced at $409, 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. Search Cheapflights for deals from Delta and Alaska Airlines - these airlines can fly you to your destination from $423 and $447, respectively. American Airlines is currently priced 43% 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 Southwest, with whom users have recently found tickets for as low as $205. However, be on the lookout for offers from Delta and Alaska 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 Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
Lansing
Hammond
Benton Harbor
Porter
Valparaiso
Chesterton

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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 July 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$419Average$623FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$429Average$718FlexibilityNo cancel feeOn-time69%
Alaska AirlinesCheapest$507Average$641FlexibilityNo cancel feeOn-time75%

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