$203 Cheap flight deals from Chicago (CHI) to Hawaii Island (KOA)

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This Weekend's Flight Deals from Chicago to Hawaii Island

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.

Sun, Dec 28 - Sat, Jan 3
MDW
Midway Intl.
KOA
Kona Intl.
$1,272 Roundtrip, found 2 days ago
$1,272
Roundtrip
found 2 days ago
Select Southwest Airlines flight, departing Sun, Dec 28 from Midway Intl. to Kona Intl., returning Sat, Jan 3, priced at $1,272 found 2 days ago
Sat, Dec 27 - Mon, Dec 29
ORD
O'Hare Intl.
KOA
Kona Intl.
$1,378 Roundtrip, found 13 hours ago
$1,378
Roundtrip
found 13 hours ago
Select Alaska Airlines flight, departing Sat, Dec 27 from O'Hare Intl. to Kona Intl., returning Mon, Dec 29, priced at $1,378 found 13 hours ago
Fri, Dec 26 - Wed, Jan 7
ORD
O'Hare Intl.
ITO
Hilo Intl.
$1,525 Roundtrip, found 2 days ago
$1,525
Roundtrip
found 2 days ago
Select Delta flight, departing Fri, Dec 26 from O'Hare Intl. to Hilo Intl., returning Wed, Jan 7, priced at $1,525 found 2 days ago

Airfares from $203 One Way, $343 Round Trip from Chicago to Hawaii Island

Prices starting at $343 for return flights and $203 for one-way flights to Hawaii Island 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, Jan 21 - Tue, Feb 3
ORD
Chicago
KOA
Kona Coast
$343 Roundtrip, found 5 days ago
$343
Roundtrip
found 5 days ago
Select Alaska Airlines flight, departing Wed, Jan 21 from Chicago to Kona Coast, returning Tue, Feb 3, priced at $343 found 5 days ago
Tue, Jan 20 - Tue, Feb 3
ORD
Chicago
KOA
Kona Coast
$352 Roundtrip, found 5 days ago
$352
Roundtrip
found 5 days ago
Select Hawaiian Airlines flight, departing Tue, Jan 20 from Chicago to Kona Coast, returning Tue, Feb 3, priced at $352 found 5 days ago
Sun, Jan 25 - Sun, Feb 1
ORD
Chicago
KOA
Kona Coast
$373 Roundtrip, found 5 days ago
$373
Roundtrip
found 5 days ago
Select Delta flight, departing Sun, Jan 25 from Chicago to Kona Coast, returning Sun, Feb 1, priced at $373 found 5 days ago
Tue, Jan 27 - Thu, Feb 5
ORD
Chicago
ITO
Hawaii Island
$432 Roundtrip, found 2 days ago
$432
Roundtrip
found 2 days ago
Select Alaska Airlines flight, departing Tue, Jan 27 from Chicago to Hawaii Island, returning Thu, Feb 5, priced at $432 found 2 days ago
Mon, Jan 19 - Mon, Jan 26
ORD
Chicago
KOA
Kona Coast
$467 Roundtrip, found 13 hours ago
$467
Roundtrip
found 13 hours ago
Select American Airlines flight, departing Mon, Jan 19 from Chicago to Kona Coast, returning Mon, Jan 26, priced at $467 found 13 hours ago

Hawaii Island economy 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)

Jan 30 - Feb 2

3 night stay

Chicago (CHI) to Kailua-Kona (KOA)

Delta • Non-stop roundtrip • Coach
Price was $1,234, price is now $801 per person
$801
per person
found 12 hours ago
Great view right in Kona across from ocean. Lovely pool. Room good size for good price.

Reviewed on Jul 29, 2025

Kona Reef, A Raintree Vacation Club Resort
3.0-star property

Kona Reef, A Raintree Vacation Club Resort

8.6/10 Excellent! (458 reviews)

Feb 4 - Feb 11

7 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 $2,908, price is now $1,358 per person
$1,358
per person
found 1 day ago
Pool, hot tub and a beautiful ocean view. Accommodations were adequate.

Reviewed on Jan 4, 2025

Lea Casa at Casa de Emdeko
3.5-star property

Lea Casa at Casa de Emdeko

9/10 Wonderful! (66 reviews)

Feb 4 - Feb 11

7 night stay

Chicago (CHI) to Kailua-Kona (KOA)

American Airlines • Non-stop • Coach

Kailua-Kona (KOA) to Chicago (CHI)

Alaska Airlines • Non-stop • Coach
Save 100% on your flight
Price was $2,299, price is now $1,410 per person
$1,410
per person
found 1 day 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

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More About Flying To Hawaii Island from Chicago

Route Information for Flights from Chicago to Hawaii Island

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

Chicago to Hawaii Island

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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.