Cheap flight from Chicago to Kailua-Kona from $450
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Flights from Chicago to Kailua-Kona
Find cheap airlines flights from Chicago to Kailua-Kona
Compare prices, find the option that best suits your travel needs, and enjoy a comfortable journey with a trusted airline.
Cheap flight deals from Chicago to Kailua-Kona
We've found these cheap flights for you. You can book one-way or round-trip flight tickets.
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ORD 7:18 PM19h 12m1 stopsKOA 9:30 AMChicago - Kailua-Kona | Mon, Aug 18 | Alaska Airlines
KOA 9:32 PM28h 31m1 stopsORD 7:03 AMKailua-Kona - Chicago | Mon, Aug 25 | Alaska Airlines$450 $75340% OFF40% OFF$753 $450 -
ORD 7:11 AM15h 27m1 stopsKOA 5:38 PMChicago - Kailua-Kona | Mon, Aug 18 | Delta Air Lines
KOA 9:45 PM21h 6m1 stopsORD 11:51 PMKailua-Kona - Chicago | Mon, Aug 25 | Delta Air Lines$472 $75337% OFF37% OFF$753 $472 -
ORD 7:15 AM15h 19m1 stopsKOA 5:34 PMChicago - Kailua-Kona | Tue, Aug 12 | Delta Air Lines
KOA 9:47 PM21h 4m1 stopsORD 11:51 PMKailua-Kona - Chicago | Tue, Aug 12 | Delta Air Lines$537 $75328% OFF28% OFF$753 $537
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ORD 8:42 PM30h 22m1 stopsKOA 10:04 PMChicago - Kailua-Kona | Mon, Aug 11 | Hawaiian Airlines
KOA 9:30 PM11h 43m1 stopsORD 2:13 PMKailua-Kona - Chicago | Sun, Aug 17 | Alaska Airlines$54328% OFF$753 $543 -
ORD 8:42 PM30h 22m1 stopsKOA 10:04 PMChicago - Kailua-Kona | Mon, Aug 11 | Alaska Airlines
KOA 9:30 PM11h 43m1 stopsORD 2:13 PMKailua-Kona - Chicago | Sun, Aug 17 | Alaska Airlines$54428% OFF$753 $544
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ORD 8:00 AM19h 4m1 stopsKOA 10:04 PMChicago - Kailua-Kona | Tue, Aug 12 | Alaska Airlines
KOA 8:00 AM23h 7m1 stopsORD 12:07 PMKailua-Kona - Chicago | Mon, Aug 18 | Alaska Airlines$55826% OFF$753 $558
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ORD 1:03 PM14h 1m1 stopsKOA 10:04 PMChicago - Kailua-Kona | Tue, Aug 5 | Alaska Airlines
KOA 9:30 PM11h 43m1 stopsORD 2:13 PMKailua-Kona - Chicago | Tue, Aug 12 | Alaska Airlines$56325% OFF$753 $563
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ORD 7:11 AM15h 23m1 stopsKOA 5:34 PMChicago - Kailua-Kona | Sun, Aug 10 | Delta Air Lines
KOA 9:47 PM14h 31m1 stopsORD 5:18 PMKailua-Kona - Chicago | Sun, Aug 17 | Delta Air Lines$56924% OFF$753 $569
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ORD 3:09 PM11h 55m1 stopsKOA 10:04 PMChicago - Kailua-Kona | Wed, Aug 6 | Alaska Airlines
KOA 8:00 AM10h 59m1 stopsORD 11:59 PMKailua-Kona - Chicago | Wed, Aug 13 | Alaska Airlines$57224% OFF$753 $572
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ORD 7:18 PM19h 12m1 stopsKOA 9:30 AMChicago - Kailua-Kona | Fri, Aug 15 | Alaska Airlines
KOA 8:00 AM23h 7m1 stopsORD 12:07 PMKailua-Kona - Chicago | Mon, Aug 18 | Alaska Airlines$57324% OFF$753 $573
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CHI 1:00 PM17h 25m1 stopsKOA Invalid DateChicago - Kailua-Kona | Sun, Jun 22 | Normal Airline
KOA 3:00 PM6hNonstopCHI 4:00 PMKailua-Kona - Chicago | Tue, Jun 24 | Normal AirlineFind More FlightsFind More Flights
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ORD 7:18 PM19h 12m1 stopsKOA 9:30 AMChicago - Kailua-Kona | Wed, Aug 13 | Alaska Airlines$238 $40441% OFF41% OFF$404 $238
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ORD 7:18 PM19h 12m1 stopsKOA 9:30 AMChicago - Kailua-Kona | Sat, Aug 16 | Alaska Airlines$261 $40436% OFF36% OFF$404 $261
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ORD 7:15 AM15h 19m1 stopsKOA 5:34 PMChicago - Kailua-Kona | Sat, Aug 16 | Delta Air Lines$271 $40433% OFF33% OFF$404 $271
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ORD 6:10 AM34h1 stopsKOA 11:10 AMChicago - Kailua-Kona | Sat, Aug 9 | Frontier Airlines$27931% OFF$404 $279 -
ORD 7:11 AM15h 27m1 stopsKOA 5:38 PMChicago - Kailua-Kona | Wed, Aug 13 | Delta Air Lines$28330% OFF$404 $283
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ORD 6:50 PM19h 40m1 stopsKOA 9:30 AMChicago - Kailua-Kona | Wed, Aug 13 | American Airlines$29427% OFF$404 $294 -
ORD 8:50 AM29h 40m1 stopsKOA 9:30 AMChicago - Kailua-Kona | Wed, Aug 13 | United Airlines$29427% OFF$404 $294 -
ORD 1:03 PM14h 1m1 stopsKOA 10:04 PMChicago - Kailua-Kona | Wed, Jul 16 | Hawaiian Airlines$29926% OFF$404 $299
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ORD 1:03 PM14h 1m1 stopsKOA 10:04 PMChicago - Kailua-Kona | Tue, Aug 5 | Alaska Airlines$30724% OFF$404 $307
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ORD 3:09 PM11h 55m1 stopsKOA 10:04 PMChicago - Kailua-Kona | Thu, Jul 31 | Alaska Airlines$30724% OFF$404 $307
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CHI 1:00 PM17h 25m1 stopsKOA Invalid DateChicago - Kailua-Kona | Sun, Jun 22 | Normal AirlineFind More FlightsFind More Flights
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Crossed out prices are calculated based on the average price of the corresponding route on Trip.com.
Flight Info | Chicago to Kailua-Kona
| Cheapest one-way flight price | $237 |
|---|---|
| Off-season for travel | March |
| Peak season for travel | May |
| Flight distance | 6,793.37 km |
| Average flight time | 9 hours 3 minutes |
| Popular airline | Alaska Airlines |
When is the cheapest time to fly from Chicago to Kailua-Kona?
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Displayed prices are calculated based on the cheapest average weekly prices of the corresponding route on Trip.com.
Frequently Asked Questions
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When are flight tickets from Chicago (CHI) to Kailua-Kona (KOA) the cheapest?
Airlines adjust prices for flights from Chicago to Kailua-Kona based on the departure date and time of your selection. By analyzing data from all airlines, we've discovered that on Trip.com, you can find the lowest flight prices on Tuesdays, Wednesdays, and Saturdays. -
How much do flights from Chicago (CHI) to Kailua-Kona (KOA) cost?
According to Trip.com's data, the lowest price is around $842. -
How long does it take to fly from Chicago (CHI) to Kailua-Kona (KOA) and what is the distance?
It takes around 9 hours 3 minutes to fly from Chicago (CHI) to Kailua-Kona (KOA). -
What are the most popular airlines that fly from Chicago (CHI) to Kailua-Kona (KOA)?
Airlines with flights from Chicago (CHI) to Kailua-Kona (KOA): United Airlines.
How to find a cheap flight from Chicago to Kailua-Kona
Wait until the last minute and flight costs are often sky-high. Plan ahead, book the right way, and your savings can soar. We have loads of saving tips to help you find a cheap flight from Chicago to Kailua-Kona. Book your flights at the right time and save more.
Be flexible with your travel dates to get the cheapest Chicago to Kailua-Kona ticket.
Tap "Date" in the flight search bar to browse the calendar and find airfare from Chicago to Kailua-Kona for the next six months in 2025. If you're looking to fly within the next three months, the lowest fare is $238 for a one-way ticket on Wed, Aug 13.
Compare cheap Chicago to Kailua-Kona flight deals from hundreds of airlines.
Our powerful search system compares prices from over 500 airlines. So you can find the cheapest flights from Chicago to Kailua-Kona. The most affordable airline currently operating on this route is Alaska Airlines.
Set up a Price Alert to track fare drops.
Set up a Price Alert for your Chicago to Kailua-Kona route to track ticket prices effortlessly—no need to check manually every day.
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Book early or wait unitl the last minute to fine the best fares.
It's always better to book early! Airlines typically release their lowest fares about a year before departure, so check as soon as flights become available. If you miss that window, you may still find great deals closer to your travel date.
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For the best booking experience on the go, download Trip.com and search for cheap flights from Chicago to Kailua-Kona to access exclusive deals just for you.
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