$209 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.

Sun, Feb 15 - Tue, Feb 24
PVD
T.F. Green
HNL
Daniel K. Inouye Intl.
$781 Roundtrip, found 1 day ago
$781
Roundtrip
found 1 day ago
Select Delta flight, departing Sun, Feb 15 from T.F. Green to Daniel K. Inouye Intl., returning Tue, Feb 24, priced at $781 found 1 day ago
Fri, Feb 13 - Sun, Feb 15
BOS
Logan Intl.
HNL
Daniel K. Inouye Intl.
$812 Roundtrip, found 4 hours ago
$812
Roundtrip
found 4 hours ago
Select Alaska Airlines flight, departing Fri, Feb 13 from Logan Intl. to Daniel K. Inouye Intl., returning Sun, Feb 15, priced at $812 found 4 hours ago

Airfares from $209 One Way, $435 Round Trip from Boston to Kailua

Prices starting at $435 for return flights and $209 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.

Mon, Feb 23 - Tue, Mar 3
BOS
Boston
HNL
Oahu
$435 Roundtrip, found 6 days ago
$435
Roundtrip
found 6 days ago
Select Alaska Airlines flight, departing Mon, Feb 23 from Boston to Oahu, returning Tue, Mar 3, priced at $435 found 6 days ago
Wed, Apr 29 - Mon, May 4
BOS
Boston
HNL
Oahu
$436 Roundtrip, found 2 days ago
$436
Roundtrip
found 2 days ago
Select Southwest Airlines flight, departing Wed, Apr 29 from Boston to Oahu, returning Mon, May 4, priced at $436 found 2 days ago
Wed, Apr 29 - Mon, May 4
BOS
Boston
HNL
Oahu
$446 Roundtrip, found 2 days ago
$446
Roundtrip
found 2 days ago
Select Southwest Airlines flight, departing Wed, Apr 29 from Boston to Oahu, returning Mon, May 4, priced at $446 found 2 days ago
Mon, Apr 27 - Mon, May 4
BOS
Boston
HNL
Oahu
$447 Roundtrip, found 3 days ago
$447
Roundtrip
found 3 days ago
Select Southwest Airlines flight, departing Mon, Apr 27 from Boston to Oahu, returning Mon, May 4, priced at $447 found 3 days ago
Mon, Apr 13 - Thu, Apr 30
PVD
Providence
HNL
Oahu
$485 Roundtrip, found 6 days ago
$485
Roundtrip
found 6 days ago
Select Delta flight, departing Mon, Apr 13 from Providence to Oahu, returning Thu, Apr 30, priced at $485 found 6 days ago

Kailua economy flight packages

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

Waikiki Circle Hotel

8.4/10 Very Good! (1,079 reviews)

Mar 12 - Mar 15

3 night stay

Boston (BOS) to Honolulu (HNL)

United • Non-stop roundtrip • Coach
Price was $1,263, price is now $946 per person
$946
per person
found 1 day ago
Rooms were very small for the rate.

Reviewed on Jan 14, 2026

Paradise Bay Resort
3.5-star property

Paradise Bay Resort

8.8/10 Excellent! (1,002 reviews)

Mar 22 - Mar 29

7 night stay

Boston (BOS) to Honolulu (HNL)

Delta • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $2,564, price is now $1,596 per person
$1,596
per person
found 1 day ago
This is a quiet little gem. Off the tourist path and scenery is spectacular. Enjoyed listening to Uncle Danny kanikapila. Tea, banana bread and coffee were yummy. Driveway, parking and stairs are a bit intimidating but just go slow. It is worth it. Am afraid to tell others about this wonderful place because I don’t want it to change. I will come again.

Reviewed on Nov 2, 2025

Waikiki Shore by OUTRIGGER
3.0-star property

Waikiki Shore by OUTRIGGER

8.4/10 Very Good! (542 reviews)

Mar 25 - Mar 30

5 night stay

Boston (BOS) to Honolulu (HNL)

United • Non-stop roundtrip • Coach
Price was $1,865, price is now $1,410 per person
$1,410
per person
found 1 day ago
This place would be 5 stars if the seating area and table on the porch were the ones pictured in the listing. The owner clearly invested a lot of time decorating their place and appointing the kitchen with lots of dishes and cooking utensils. However, most, ironically, there is absolutely nowhere to sit and enjoy a meal, unless you want to stare at a wall and sit on a barstool. The outside table and chairs are not the one picture, and seem to be available only to drink cocktails, not to eat a meal. We found ourselves, unable to prepare a lot of food and needing to go out to restaurants because there was no seating area.

Reviewed on Feb 23, 2025

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Kailua first class flight packages

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

Waikiki Resort Hotel

8.6/10 Excellent! (2,635 reviews)

Mar 21 - Mar 25

4 night stay

Boston (BOS) to Honolulu (HNL)

Delta • Non-stop roundtrip • FirstClass
Price was $2,369, price is now $2,080 per person
$2,080
per person
found 20 hours ago
It was a great place to stay

Reviewed on Nov 21, 2025

Waikiki Circle Hotel
3.0-star property

Waikiki Circle Hotel

8.4/10 Very Good! (1,079 reviews)

Mar 21 - Mar 25

4 night stay

Boston (BOS) to Honolulu (HNL)

Delta • Non-stop roundtrip • FirstClass
Price was $2,429, price is now $2,127 per person
$2,127
per person
found 20 hours ago
Rooms were very small for the rate.

Reviewed on Jan 14, 2026

Prince Waikiki
4.5-star property

Prince Waikiki

9.4/10 Exceptional! (3,326 reviews)

Mar 21 - Mar 25

4 night stay

Boston (BOS) to Honolulu (HNL)

Delta • Non-stop roundtrip • FirstClass
Price was $2,566, price is now $2,260 per person
$2,260
per person
found 20 hours ago
Excellent property. Great service, great amenities. On the quiet end of Waikiki. Loved our visit!

Reviewed on Dec 31, 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.