$196 Cheap flight deals from Chicago (CHI) to Waikoloa (KOA)

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This Weekend's Flight Deals from Chicago to Waikoloa

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.

Sat, Jan 31 - Thu, Feb 12
ORD
O'Hare Intl.
KOA
Kona Intl.
$618 Roundtrip, found 4 days ago
$618
Roundtrip
found 4 days ago
Select Delta flight, departing Sat, Jan 31 from O'Hare Intl. to Kona Intl., returning Thu, Feb 12, priced at $618 found 4 days ago

Airfares from $196 One Way, $363 Round Trip from Chicago to Waikoloa

Prices starting at $363 for return flights and $196 for one-way flights to Waikoloa were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Wed, Feb 25 - Thu, Mar 5
ORD
Chicago
KOA
Kona Coast
$363 Roundtrip, found 6 days ago
$363
Roundtrip
found 6 days ago
Select Hawaiian Airlines flight, departing Wed, Feb 25 from Chicago to Kona Coast, returning Thu, Mar 5, priced at $363 found 6 days ago
Thu, Mar 5 - Tue, Mar 10
ORD
Chicago
KOA
Kona Coast
$367 Roundtrip, found 6 days ago
$367
Roundtrip
found 6 days ago
Select Delta flight, departing Thu, Mar 5 from Chicago to Kona Coast, returning Tue, Mar 10, priced at $367 found 6 days ago
Tue, Feb 24 - Thu, Mar 5
ORD
Chicago
KOA
Kona Coast
$372 Roundtrip, found 6 days ago
$372
Roundtrip
found 6 days ago
Select Hawaiian Airlines flight, departing Tue, Feb 24 from Chicago to Kona Coast, returning Thu, Mar 5, priced at $372 found 6 days ago
Wed, Mar 4 - Tue, Mar 10
ORD
Chicago
KOA
Kona Coast
$377 Roundtrip, found 6 days ago
$377
Roundtrip
found 6 days ago
Select Hawaiian Airlines flight, departing Wed, Mar 4 from Chicago to Kona Coast, returning Tue, Mar 10, priced at $377 found 6 days ago
Tue, Apr 14 - Tue, Apr 21
ORD
Chicago
KOA
Kona Coast
$402 Roundtrip, found 4 days ago
$402
Roundtrip
found 4 days ago
Select Bargain Flight flight, departing Tue, Apr 14 from Chicago to Kona Coast, returning Tue, Apr 21, priced at $402 found 4 days ago

Waikoloa economy flight packages

Price found within the past 48 hours. Click for updated prices.
Lea Casa at Casa de Emdeko
3.5-star property

Lea Casa at Casa de Emdeko

9/10 Wonderful! (66 reviews)

Mar 21 - Mar 25

4 night stay

Chicago (CHI) to Kailua-Kona (KOA)

Southwest Airlines • Coach

Kailua-Kona (KOA) to Chicago (CHI)

American Airlines • Coach
Price was $1,621, price is now $1,183 per person
$1,183
per person
found 22 hours ago
It was comfortable, and clean overall. The unit was well stocked with basics for cooking and storing leftovers. The grounds were nice, and we loved the saltwater pool and the tables by the cabana. Having free parking was great too.

Reviewed on Nov 26, 2025

Royal Sea Cliff Kona by OUTRIGGER
3.0-star property

Royal Sea Cliff Kona by OUTRIGGER

8.6/10 Excellent! (553 reviews)

Mar 10 - Mar 15

5 night stay

Chicago (CHI) to Kailua-Kona (KOA)

American Airlines • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $1,696, price is now $1,194 per person
$1,194
per person
found 16 hours ago
This place is amazing!! Everyone was so nice and the view was amazing! We stayed in room 715. 2 bedroom and 2 bath, A/C, and washer and dryer in the condo. We walked to town, but we also had a car to drive around. If you or a family member has food allergies, this is a great place to stay with a full kitchen. The grocery store is only 10 minutes away.

Reviewed on Jun 21, 2025

Mauna Lani, Auberge Collection
5.0-star property

Mauna Lani, Auberge Collection

9.4/10 Exceptional! (1,002 reviews)

Mar 21 - Mar 25

4 night stay

Chicago (CHI) to Kailua-Kona (KOA)

Southwest Airlines • Coach

Kailua-Kona (KOA) to Chicago (CHI)

American Airlines • Coach
Save 100% on your flight
Price was $3,270, price is now $2,397 per person
$2,397
per person
found 22 hours 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

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Waikoloa first class flight packages

Price found within the past 48 hours. Click for updated prices.
Kona Islander Vacation Club
2.5-star property

Kona Islander Vacation Club

7/10 Good! (333 reviews)

Mar 14 - Mar 21

7 night stay

Chicago (CHI) to Kailua-Kona (KOA)

American Airlines • Non-stop • FirstClass

Kailua-Kona (KOA) to Chicago (CHI)

Alaska Airlines • Non-stop • FirstClass
Price was $4,191, price is now $3,495 per person
$3,495
per person
found 1 day ago
Great view right in Kona across from ocean. Lovely pool. Room good size for good price.

Reviewed on Jul 29, 2025

Mauna Lani, Auberge Collection
5.0-star property

Mauna Lani, Auberge Collection

9.4/10 Exceptional! (1,002 reviews)

Mar 14 - Mar 21

7 night stay

Chicago (CHI) to Kailua-Kona (KOA)

American Airlines • Non-stop • FirstClass

Kailua-Kona (KOA) to Chicago (CHI)

Alaska Airlines • Non-stop • FirstClass
Price was $8,147, price is now $6,523 per person
$6,523
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

OUTRIGGER Kona Resort and Spa
4.0-star property

OUTRIGGER Kona Resort and Spa

8.6/10 Excellent! (1,004 reviews)

Mar 14 - Mar 21

7 night stay

Chicago (CHI) to Kailua-Kona (KOA)

American Airlines • Non-stop • FirstClass

Kailua-Kona (KOA) to Chicago (CHI)

Alaska Airlines • Non-stop • FirstClass
Price was $4,535, price is now $3,905 per person
$3,905
per person
found 1 day ago
Staff was great and Room 4366 was great (though the bedside clock needs replacing -- it kept losing the right time)

Reviewed on Jan 15, 2026

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More About Flying To Waikoloa from Chicago

Route Information for Flights from Chicago to Waikoloa

Origin Airport IATA Code
CHI
Destination Airport IATA Code
KOA
Distance
Direct Flight Airlines
Earliest Flight Arrival
Latest Flight Arrival

Chicago to Waikoloa

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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.