$190 Cheap flight deals from Chicago (CHI) to Kailua-Kona (KOA)
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This Weekend's Flight Deals from Chicago to Kailua-Kona
This weekend's flight prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.
ORD
O'Hare Intl.
KOA
Kona Intl.
$728 Roundtrip, found 4 days ago
$728
Roundtrip
found 4 days ago
Airfares from $190 One Way, $364 Round Trip from Chicago to Kailua-Kona
Prices starting at $364 for return flights and $190 for one-way flights to Kailua-Kona were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.
ORD
Chicago
KOA
Kona Coast
$364 Roundtrip, found 14 hours ago
$364
Roundtrip
found 14 hours ago
ORD
Chicago
KOA
Kona Coast
$376 Roundtrip, found 4 hours ago
$376
Roundtrip
found 4 hours ago
ORD
Chicago
ITO
Hawaii Island
$395 Roundtrip, found 6 days ago
$395
Roundtrip
found 6 days ago
ORD
Chicago
KOA
Kona Coast
$405 Roundtrip, found 14 hours ago
$405
Roundtrip
found 14 hours ago
ORD
Chicago
KOA
Kona Coast
$445 Roundtrip, found 3 hours ago
$445
Roundtrip
found 3 hours ago
Kailua-Kona economy flight packages
Price found within the past 48 hours. Click for updated prices.
2.0-star property
Kehena Mauka Nui LGBTQ Clothing Optional
9.8/10 Exceptional! (9 reviews)
Dec 11 - Dec 14
3 night stay
Chicago (CHI) to Hilo (ITO)
American Airlines • Non-stop • Coach
Hilo (ITO) to Chicago (CHI)
Alaska Airlines • Non-stop • Coach
Price was $744, price is now $534 per person
$534
per person
found 1 day ago
We loved our stay at Kehena house! We were greeted by Stephen when we arrived and given a quick tour. They were hosting a Pride potluck that day and he kindly invited us to come eat and join in as guests of the house. Everyone we met was friendly and we felt safe to be ourselves. In the room, there was a list of unique weekly activities and opportunities near by, which made the experience feel even more welcoming.
The property is *amazing*. Might as well be a mini botanical gardens between the flowers, fawna, and the fruit trees. You can tell its cared for, but not obsessively manicured, a natural look. The inside of the house looks better than the pictures, perfectly clean. Thoughtful touches as well. I selected the room that is more exposed to the outside night noises, and ear plugs were provided (i didnt need them, I enjoyed the experience). There is a house cat, but she minds to herself and was friendly when approached. I enjoyed the serenity of the outdoor shower one morning. It was so peaceful, great water pressure too. The bathtub available is deep and looked great for soaking tired traveler muscles, but I didnt use it.
We did walk down to the beach. There is no specific easy path down, but there are some trails and it wasnt too difficult. The water was way too rough to get in when we visited, but we got some great pics.
I plan to stay here again next time I visit Hawaii.
Reviewed on Jul 12, 2025
5.0-star property
Mauna Lani, Auberge Collection
9.4/10 Exceptional! (1,008 reviews)
Dec 11 - Dec 14
3 night stay
Chicago (CHI) to Kailua-Kona (KOA)
American Airlines • Non-stop • Coach
Kailua-Kona (KOA) to Chicago (CHI)
Alaska Airlines • Non-stop • Coach
Price was $2,461, price is now $1,587 per person
$1,587
per person
found 1 day ago
Excellent dining options at the Auberge at the Canoe House and the Halani. Well situated to walk to the nearby protected cove for snorkeling passing ancient Hawaiian fish ponds along the way. Heading in the opposite direction is the beach trail to the Fairmont Orchid which also has a nice sheltered cove for snorkeling and an excellent restaurant (Browns) for a special dining experience. At the Auberge we got to see a turtle swimming in the water near the beach. We also loved the morning complementary yoga classes and it was a nice surprise that there was also an adult only pool. Mahalo to the staff who were everyone of them very friendly.
Reviewed on Sep 1, 2025
4.0-star property
Aston Kona by the Sea
8.8/10 Excellent! (1,124 reviews)
Dec 11 - Dec 14
3 night stay
Chicago (CHI) to Kailua-Kona (KOA)
American Airlines • Non-stop • Coach
Kailua-Kona (KOA) to Chicago (CHI)
Alaska Airlines • Non-stop • Coach
Price was $1,172, price is now $825 per person
$825
per person
found 1 day ago
Well kept and a cut above most of the surrounding Condo complexes plus it has central air conditioning,….and right on the Besch.
Reviewed on Aug 7, 2025
Kailua-Kona first class flight packages
Price found within the past 48 hours. Click for updated prices.
3.5-star property
Courtyard by Marriott King Kamehameha's Kona Beach Hotel
8.4/10 Very Good! (1,010 reviews)
Dec 22 - Dec 30
8 night stay
Chicago (ORD) to Kailua-Kona (KOA)
American Airlines • Non-stop roundtrip • FirstClass
Price was $5,000, price is now $4,282 per person
$4,282
per person
found 1 day ago
Room needs renovation, pool area is too small and the ocean front area is not private and is too crowded. The only thing is good about this hotel is location.
Reviewed on Aug 8, 2025
4.0-star property
Waikoloa Beach Marriott Resort & Spa
8.6/10 Excellent! (1,001 reviews)
Dec 22 - Dec 30
8 night stay
Chicago (ORD) to Kailua-Kona (KOA)
American Airlines • Non-stop roundtrip • FirstClass
Price was $5,710, price is now $5,615 per person
$5,615
per person
found 1 day ago
Closer to the beach. Shopping areas around the property. Limited house keeping. Front desk customer service not much helpful, could have been better.
Reviewed on Mar 26, 2025
More About Flying To Kailua-Kona from Chicago
Route Information for Flights from Chicago to Kailua-Kona
Origin Airport IATA Code | CHI |
|---|---|
Destination Airport IATA Code | KOA |
Distance | |
Direct Flight Airlines | |
Earliest Flight Arrival | |
Latest Flight Arrival |
Chicago to Kailua-Kona
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Flights to Kailua-Kona
- Newark to Kailua-Kona
- Honolulu to Kailua-Kona
- Hilo to Kailua-Kona
- Eureka to Kailua-Kona
- Chicago to Kailua-Kona
- Houston to Kailua-Kona
- Los Angeles to Kailua-Kona
- New York to Kailua-Kona
- Orlando to Kailua-Kona
- San Francisco to Kailua-Kona
- Stockholm to Kailua-Kona
- Toronto to Kailua-Kona
- Washington to Kailua-Kona
- Sacramento to Kailua-Kona
- Accra to Kailua-Kona
- Amman to Kailua-Kona
- El Paso to Kailua-Kona
- Fukuoka to Kailua-Kona
- Guadalajara to Kailua-Kona
- Grand Junction to Kailua-Kona
Flights from Chicago
- Chicago to Orlando
- Chicago to Houston
- Chicago to New York
- Chicago to Phoenix
- Chicago to Dallas
- Chicago to Los Angeles
- Chicago to London
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- Chicago to Rome
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- Chicago to Hartford
- Chicago to Atlantic City
Kailua-Kona Airports
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- Flights from Comox (YQQ) to Kailua-Kona (KOA)
- Flights from Yuma (YUM) to Kailua-Kona (KOA)
Fare, taxes & fees: Fares include all taxes and fees, except baggage fees. Rates shown reflect fares found by other Orbitz users over the past 7 days. Due to rapidly changing airline prices & seat availability, these fares may no longer be available.
Refunds/changes/cancellations: Itinerary changes, if permitted for the fare, will have a $30 service fee charged by Orbitz. Additional airline charges may apply.
Other conditions: Schedules, fares and rules are subject to change without notice. Seats are limited and may not be available on all flights/dates or in all markets. Lower fares may be available. Fares will not be honored retroactively or in exchange for any wholly/partially unused ticket. Tickets are non-transferable and non-refundable. Fare rules are provided for the selected itinerary before booking.