$236 Cheap flight deals from Boston (BOS) to Kailua (HNL)

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This Weekend's Flight Deals from Boston to Kailua

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, Nov 14 - Fri, Nov 21
BOS
Logan Intl.
HNL
Daniel K. Inouye Intl.
$654 Roundtrip, found 6 days ago
$654
Roundtrip
found 6 days ago
Select Southwest Airlines flight, departing Fri, Nov 14 from Logan Intl. to Daniel K. Inouye Intl., returning Fri, Nov 21, priced at $654 found 6 days ago

Airfares from $236 One Way, $481 Round Trip from Boston to Kailua

Prices starting at $481 for return flights and $236 for one-way flights to Kailua 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 18 - Mon, Mar 2
BOS
Boston
HNL
Oahu
$481 Roundtrip, found 3 days ago
$481
Roundtrip
found 3 days ago
Select Alaska Airlines flight, departing Wed, Feb 18 from Boston to Oahu, returning Mon, Mar 2, priced at $481 found 3 days ago
Sat, Feb 14 - Wed, Feb 25
BOS
Boston
HNL
Oahu
$556 Roundtrip, found 1 day ago
$556
Roundtrip
found 1 day ago
Select Southwest Airlines flight, departing Sat, Feb 14 from Boston to Oahu, returning Wed, Feb 25, priced at $556 found 1 day ago
Thu, Feb 5 - Thu, Feb 12
BOS
Boston
HNL
Oahu
$557 Roundtrip, found 1 hour ago
$557
Roundtrip
found 1 hour ago
Select United flight, departing Thu, Feb 5 from Boston to Oahu, returning Thu, Feb 12, priced at $557 found 1 hour ago
Wed, Dec 3 - Wed, Dec 10
BOS
Boston
HNL
Oahu
$567 Roundtrip, found 11 hours ago
$567
Roundtrip
found 11 hours ago
Select Delta flight, departing Wed, Dec 3 from Boston to Oahu, returning Wed, Dec 10, priced at $567 found 11 hours ago
Sat, Jan 31 - Wed, Feb 4
PVD
Providence
HNL
Oahu
$572 Roundtrip, found 6 days ago
$572
Roundtrip
found 6 days ago
Select Delta flight, departing Sat, Jan 31 from Providence to Oahu, returning Wed, Feb 4, priced at $572 found 6 days ago

Kailua economy flight packages

Price found within the past 48 hours. Click for updated prices.
Stay Hotel Waikiki
3.0-star property

Stay Hotel Waikiki

7.8/10 Good! (1,311 reviews)

Dec 21 - Dec 28

7 night stay

Boston (BOS) to Honolulu (HNL)

United • Roundtrip • Coach
Price was $2,230, price is now $1,558 per person
$1,558
per person
found 1 day ago
Great affordable hotel in great location

Reviewed on Oct 14, 2025

Prince Waikiki
4.5-star property

Prince Waikiki

9.4/10 Exceptional! (3,321 reviews)

Dec 21 - Dec 28

7 night stay

Boston (BOS) to Honolulu (HNL)

United • Roundtrip • Coach
Save 100% on your flight
Price was $3,523, price is now $2,442 per person
$2,442
per person
found 1 day ago
100 Sail Restaurant: food selection and quality, very poor; table service was worse. We may stay at the Prince Waikiki again but will never dine there. Period.

Reviewed on Mar 12, 2025

OUTRIGGER Waikiki Paradise Hotel
4.0-star property

OUTRIGGER Waikiki Paradise Hotel

9.2/10 Wonderful! (885 reviews)

Dec 21 - Dec 28

7 night stay

Boston (BOS) to Honolulu (HNL)

United • Roundtrip • Coach
Price was $2,916, price is now $2,031 per person
$2,031
per person
found 1 day ago
MY STAY AT YOUR HOTEL WAS VERY NICE. ALL MY NEEDS WERE TAKEN CARE OFF.

Reviewed on Sep 27, 2025

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Kailua first class flight packages

Price found within the past 48 hours. Click for updated prices.
Courtyard by Marriott Waikiki Beach
3.0-star property

Courtyard by Marriott Waikiki Beach

7.4/10 Good! (1,001 reviews)

Dec 26 - Jan 3

8 night stay

Boston (BOS) to Honolulu (HNL)

Delta • Non-stop • FirstClass

Honolulu (HNL) to Boston (BOS)

United • Non-stop • FirstClass
Price was $4,732, price is now $4,504 per person
$4,504
per person
found 12 hours ago
Good place to stay for a few nights. They are trying to renovate the hotel so that may turn people off. We only had an issue with the water in the shower not working. The room was clean, the pools were great and staff were outstanding.

Reviewed on Nov 5, 2024

Sheraton Waikiki Beach Resort
4.5-star property

Sheraton Waikiki Beach Resort

9.2/10 Wonderful! (2,608 reviews)

Dec 26 - Jan 3

8 night stay

Boston (BOS) to Honolulu (HNL)

Delta • Non-stop • FirstClass

Honolulu (HNL) to Boston (BOS)

United • Non-stop • FirstClass
Price was $7,698, price is now $7,099 per person
$7,099
per person
found 12 hours ago
the best place to stay

Reviewed on Oct 26, 2025

The Royal Hawaiian, a Luxury Collection Resort, Waikiki
5.0-star property

The Royal Hawaiian, a Luxury Collection Resort, Waikiki

9.2/10 Wonderful! (1,018 reviews)

Dec 26 - Jan 3

8 night stay

Boston (BOS) to Honolulu (HNL)

Delta • Non-stop • FirstClass

Honolulu (HNL) to Boston (BOS)

United • Non-stop • FirstClass
Price was $8,501, price is now $8,476 per person
$8,476
per person
found 12 hours ago
We really enjoyed our stay at this iconic hotel. The staff and service was world class. There are so many different restaurants within easy walking distance and the beach access was super easy. The pool area was a favorite for our 7 year old, as well as the koi pond and the daily feeding experience. A very enjoyable stay for sure.

Reviewed on Oct 20, 2025

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More About Flying To Kailua from Boston

Route Information for Flights from Boston to Kailua

Origin Airport IATA Code
BOS
Destination Airport IATA Code
HNL
Distance
Direct Flight Airlines
Earliest Flight Arrival
Latest Flight Arrival

Boston to Kailua

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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.