$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 15 hours ago
$781
Roundtrip
found 15 hours 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 15 hours ago
Sat, Feb 14 - Sun, Feb 22
BOS
Logan Intl.
HNL
Daniel K. Inouye Intl.
$890 Roundtrip, found 2 hours ago
$890
Roundtrip
found 2 hours ago
Select Delta flight, departing Sat, Feb 14 from Logan Intl. to Daniel K. Inouye Intl., returning Sun, Feb 22, priced at $890 found 2 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 5 days ago
$435
Roundtrip
found 5 days ago
Select Alaska Airlines flight, departing Mon, Feb 23 from Boston to Oahu, returning Tue, Mar 3, priced at $435 found 5 days ago
Wed, Apr 29 - Mon, May 4
BOS
Boston
HNL
Oahu
$436 Roundtrip, found 1 day ago
$436
Roundtrip
found 1 day ago
Select Southwest Airlines flight, departing Wed, Apr 29 from Boston to Oahu, returning Mon, May 4, priced at $436 found 1 day ago
Wed, Apr 29 - Tue, May 5
BOS
Boston
HNL
Oahu
$441 Roundtrip, found 6 days ago
$441
Roundtrip
found 6 days ago
Select Southwest Airlines flight, departing Wed, Apr 29 from Boston to Oahu, returning Tue, May 5, priced at $441 found 6 days ago
Wed, Apr 29 - Mon, May 4
BOS
Boston
HNL
Oahu
$446 Roundtrip, found 1 day ago
$446
Roundtrip
found 1 day ago
Select Southwest Airlines flight, departing Wed, Apr 29 from Boston to Oahu, returning Mon, May 4, priced at $446 found 1 day ago
Mon, Apr 13 - Thu, Apr 30
PVD
Providence
HNL
Oahu
$485 Roundtrip, found 5 days ago
$485
Roundtrip
found 5 days ago
Select Delta flight, departing Mon, Apr 13 from Providence to Oahu, returning Thu, Apr 30, priced at $485 found 5 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! (1,357 reviews)

Mar 13 - Mar 17

4 night stay

Boston (BOS) to Honolulu (HNL)

Alaska Airlines • Non-stop roundtrip • Coach
Price was $1,238, price is now $901 per person
$901
per person
found 1 day ago
One block away from Kalākaua behind the Hyatt. It’ll get a tad bit noisy depending on where your room faces but bring some ear plugs and you’ll be fine. The staff were seriously one of the nicest I’ve ever experienced in a hotel. The free coffee and laundry made the entire stay well worth it.

Reviewed on Jan 19, 2026

Ilikai by Luana Hawaii Vacation Rentals
3.0-star property

Ilikai by Luana Hawaii Vacation Rentals

8.6/10 Excellent! (51 reviews)

Mar 18 - Mar 23

5 night stay

Boston (BOS) to Honolulu (HNL)

United • Non-stop roundtrip • Coach
Price was $3,587, price is now $1,580 per person
$1,580
per person
found 1 day ago
The room was fully furnished with everything we needed. No washing machine but that was minor. Awesome view. Valet parking was great!!! Will book again.

Reviewed on Aug 13, 2025

Paradise Bay Resort
3.5-star property

Paradise Bay Resort

8.8/10 Excellent! (1,002 reviews)

Mar 25 - Mar 30

5 night stay

Boston (BOS) to Honolulu (HNL)

United • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $1,875, price is now $1,177 per person
$1,177
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

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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.