$244 Cheap flight deals from Chicago (CHI) to Captain Cook (KOA)

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This Weekend's Flight Deals from Chicago to Captain Cook

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.

Fri, Sep 11 - Sat, Sep 19
ORD
O'Hare Intl.
KOA
Kona Intl.
$693 Roundtrip, found 2 days ago
$693
Roundtrip
found 2 days ago
Select Bargain Flight flight, departing Fri, Sep 11 from O'Hare Intl. to Kona Intl., returning Sat, Sep 19, priced at $693 found 2 days ago
Sat, Sep 12 - Sat, Sep 26
MDW
Midway Intl.
KOA
Kona Intl.
$735 Roundtrip, found 4 days ago
$735
Roundtrip
found 4 days ago
Select Delta flight, departing Sat, Sep 12 from Midway Intl. to Kona Intl., returning Sat, Sep 26, priced at $735 found 4 days ago

Airfares from $244 One Way, $431 Round Trip from Chicago to Captain Cook

Prices starting at $431 for return flights and $244 for one-way flights to Captain Cook 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, Dec 2 - Fri, Dec 11
ORD
Chicago
KOA
Kona Coast
$431 Roundtrip, found 1 day ago
$431
Roundtrip
found 1 day ago
Select Bargain Flight flight, departing Wed, Dec 2 from Chicago to Kona Coast, returning Fri, Dec 11, priced at $431 found 1 day ago
Sat, Oct 24 - Mon, Nov 2
ORD
Chicago
KOA
Kona Coast
$440 Roundtrip, found 2 days ago
$440
Roundtrip
found 2 days ago
Select Bargain Flight flight, departing Sat, Oct 24 from Chicago to Kona Coast, returning Mon, Nov 2, priced at $440 found 2 days ago
Wed, Jan 20 - Sun, Jan 24
ORD
Chicago
KOA
Kona Coast
$446 Roundtrip, found 1 day ago
$446
Roundtrip
found 1 day ago
Select Delta flight, departing Wed, Jan 20 from Chicago to Kona Coast, returning Sun, Jan 24, priced at $446 found 1 day ago
Wed, Dec 2 - Tue, Dec 8
ORD
Chicago
KOA
Kona Coast
$446 Roundtrip, found 8 hours ago
$446
Roundtrip
found 8 hours ago
Select Alaska Airlines flight, departing Wed, Dec 2 from Chicago to Kona Coast, returning Tue, Dec 8, priced at $446 found 8 hours ago
Sun, Oct 25 - Thu, Nov 12
ORD
Chicago
KOA
Kona Coast
$452 Roundtrip, found 3 hours ago
$452
Roundtrip
found 3 hours ago
Select Alaska Airlines flight, departing Sun, Oct 25 from Chicago to Kona Coast, returning Thu, Nov 12, priced at $452 found 3 hours ago

Captain Cook economy flight packages

Price found within the past 48 hours. Click for updated prices.
OUTRIGGER Kona Resort & Spa
4.0-star property

OUTRIGGER Kona Resort & Spa

8.8/10 Excellent! (1,211 reviews)

Oct 31 - Nov 7

7 night stay

Chicago (CHI) to Kailua-Kona (KOA)

Alaska Airlines • Non-stop • Coach

Kailua-Kona (KOA) to Chicago (CHI)

Delta • Non-stop • Coach
Price was $1,972, price is now $1,403 per person
$1,403
per person
found 1 day ago

Fairmont Orchid
4.5-star property

Fairmont Orchid

9.2/10 Wonderful! (1,006 reviews)

Oct 31 - Nov 7

7 night stay

Chicago (CHI) to Kailua-Kona (KOA)

Alaska Airlines • Non-stop • Coach

Kailua-Kona (KOA) to Chicago (CHI)

Delta • Non-stop • Coach
Price was $2,851, price is now $2,094 per person
$2,094
per person
found 1 day ago
The staff, food and view were incredible. The room could be cleaner we were upgraded to a suite for an extra cost and the sink knobs were rusted, the tub was growing mold in small areas and glass doors and closer mirror doors were not clean. We stayed for 5 nights and used the dining table often it was never cleaned the entire time we were there. We also encounter large cockroaches at the gift shop and near the room. Made staff aware right before checking out and their response was thank you we will pass it on to management,

Reviewed on Sep 1, 2026

Fairmont Orchid Gold Experience
5.0-star property

Fairmont Orchid Gold Experience

9.4/10 Exceptional! (93 reviews)

Oct 31 - Nov 7

7 night stay

Chicago (CHI) to Kailua-Kona (KOA)

Alaska Airlines • Non-stop • Coach

Kailua-Kona (KOA) to Chicago (CHI)

Delta • Non-stop • Coach
Price was $4,255, price is now $3,203 per person
$3,203
per person
found 1 day ago

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More About Flying To Captain Cook from Chicago

Route Information for Flights from Chicago to Captain Cook

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

Chicago to Captain Cook

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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.