$100 Cheap flight deals from Boston (BOS) to Middlesex County (KIN)

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This Weekend's Flight Deals from Boston to Middlesex County

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.

Sat, Aug 9 - Thu, Aug 14
BOS
Logan Intl.
MBJ
Sir Donald Sangster Intl.
$427 Roundtrip, found 13 hours ago
$427
Roundtrip
found 13 hours ago
Select Spirit Airlines flight, departing Sat, Aug 9 from Logan Intl. to Sir Donald Sangster Intl., returning Thu, Aug 14, priced at $427 found 13 hours ago
Sat, Aug 9 - Sat, Aug 16
PVD
T.F. Green
MBJ
Sir Donald Sangster Intl.
$525 Roundtrip, found 3 days ago
$525
Roundtrip
found 3 days ago
Select JetBlue Airways flight, departing Sat, Aug 9 from T.F. Green to Sir Donald Sangster Intl., returning Sat, Aug 16, priced at $525 found 3 days ago
Fri, Aug 8 - Wed, Aug 27
ORH
Worcester Regional
MBJ
Sir Donald Sangster Intl.
$539 Roundtrip, found 2 days ago
$539
Roundtrip
found 2 days ago
Select JetBlue Airways flight, departing Fri, Aug 8 from Worcester Regional to Sir Donald Sangster Intl., returning Wed, Aug 27, priced at $539 found 2 days ago
Fri, Aug 8 - Fri, Aug 15
BOS
Logan Intl.
KIN
Norman Manley Intl.
$644 Roundtrip, found 1 day ago
$644
Roundtrip
found 1 day ago
Select Spirit Airlines flight, departing Fri, Aug 8 from Logan Intl. to Norman Manley Intl., returning Fri, Aug 15, priced at $644 found 1 day ago

Airfares from $100 One Way, $247 Round Trip from Boston to Middlesex County

Prices starting at $247 for return flights and $100 for one-way flights to Middlesex County were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Tue, Sep 2 - Tue, Sep 9
BOS
Boston
MBJ
Montego Bay
$247 Roundtrip, found 6 hours ago
$247
Roundtrip
found 6 hours ago
Select Spirit Airlines flight, departing Tue, Sep 2 from Boston to Montego Bay, returning Tue, Sep 9, priced at $247 found 6 hours ago
Mon, Sep 15 - Fri, Sep 19
BOS
Boston
MBJ
Montego Bay
$335 Roundtrip, found 3 days ago
$335
Roundtrip
found 3 days ago
Select Delta flight, departing Mon, Sep 15 from Boston to Montego Bay, returning Fri, Sep 19, priced at $335 found 3 days ago
Tue, Sep 2 - Sat, Sep 13
BOS
Boston
MBJ
Montego Bay
$346 Roundtrip, found 6 hours ago
$346
Roundtrip
found 6 hours ago
Select JetBlue Airways flight, departing Tue, Sep 2 from Boston to Montego Bay, returning Sat, Sep 13, priced at $346 found 6 hours ago
Sat, Aug 30 - Sat, Sep 6
MHT
Manchester
MBJ
Montego Bay
$420 Roundtrip, found 5 days ago
$420
Roundtrip
found 5 days ago
Select American Airlines flight, departing Sat, Aug 30 from Manchester to Montego Bay, returning Sat, Sep 6, priced at $420 found 5 days ago
Wed, Oct 1 - Mon, Oct 6
BOS
Boston
KIN
Kingston
$420 Roundtrip, found 2 days ago
$420
Roundtrip
found 2 days ago
Select JetBlue Airways flight, departing Wed, Oct 1 from Boston to Kingston, returning Mon, Oct 6, priced at $420 found 2 days ago

Middlesex County economy flight packages

Price found within the past 48 hours. Click for updated prices.
Sunset at the Palms Resort - Adults Only - All Inclusive
4.5-star property

Sunset at the Palms Resort - Adults Only - All Inclusive

9/10 Wonderful! (1,002 reviews)

Sep 17 - Sep 21

4 night stay

Boston (BOS) to Montego Bay (MBJ)

JetBlue Airways • Non-stop • Coach

Montego Bay (MBJ) to Boston (BOS)

Frontier Airlines • Non-stop • Coach
Save 100% on your flight
per person
found 1 day ago
Staff is friendly and nice. Service is inconsistent across all areas. Room was ok but I had a bad ant problem twice. They took care of it each time but still not ideal. Food was great and beach is nice but again the long wait times and inconsistent service soured the experience.

Reviewed on Jan 22, 2025

Princess Grand Jamaica Resort - All Inclusive
4.5-star property

Princess Grand Jamaica Resort - All Inclusive

9/10 Wonderful! (260 reviews)

Sep 7 - Sep 13

6 night stay

Boston (BOS) to Montego Bay (MBJ)

Spirit Airlines • Non-stop roundtrip • Coach
per person
found 18 hours ago
The staff wasnt nice and there was nothing over that way in Greenland, the staff in tropical tours were scammers.they had different proces for the same trip every day. I wouldnt recommend

Reviewed on Jul 19, 2025

Princess Senses The Mangrove Resort - Adults Only
4.0-star property

Princess Senses The Mangrove Resort - Adults Only

9.2/10 Wonderful! (236 reviews)

Sep 17 - Sep 21

4 night stay

Boston (BOS) to Montego Bay (MBJ)

JetBlue Airways • Non-stop • Coach

Montego Bay (MBJ) to Boston (BOS)

Frontier Airlines • Non-stop • Coach
per person
found 1 day ago
This resort has the perfect set up and has amazing staff. Very friendly, personable, and high energy (thanks keno) especially when it comes to the evening activities. Scuba diving and catamaran tours will leave directly from the resort beach. Super convenient.

Reviewed on Feb 25, 2025

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Middlesex County business class flight packages

Price found within the past 48 hours. Click for updated prices.
Couples Sans Souci All Inclusive
5.0-star property

Couples Sans Souci All Inclusive

9.2/10 Wonderful! (807 reviews)

Sep 8 - Sep 15

7 night stay

Boston (BOS) to Montego Bay (MBJ)

Delta • Non-stop • BusinessClass

Montego Bay (MBJ) to Boston (BOS)

American Airlines • Non-stop • BusinessClass
per person
found 4 hours ago
If you’re looking for a resort with a beautiful botanical garden setting, great food, pool and beach area look no further. The secluded au naturel beach and pool nestled away on the property is the cherry on top that you didn’t know you needed in life. Book the trip, thank me later.

Reviewed on Mar 9, 2025

Sandals Negril - ALL INCLUSIVE Couples Only
4.5-star property

Sandals Negril - ALL INCLUSIVE Couples Only

8.2/10 Very Good! (221 reviews)

Sep 8 - Sep 15

7 night stay

Boston (BOS) to Montego Bay (MBJ)

Delta • Non-stop • BusinessClass

Montego Bay (MBJ) to Boston (BOS)

American Airlines • Non-stop • BusinessClass
per person
found 4 hours ago
Some of the staff were standouts; bartenders Chris and Brendon, dive team members Emron and Robin. The entertainment team were great, especially for the dated equipment and staging that they have to use. Though they should use more travelling shows to up the quality and variety. We enjoyed all of the restaurants, but the breakfast and lunch buffet were a little lacking. The resort is a little dated, but fairly well maintained. Could use more staff or do a better job of picking up used glasses, trash and dishes. Probably our biggest complaint are the number of chairs tied up by the butlers that never get used all day long. You should not have to get up at 6am to reserve a spot, and then sit and see empty chairs all day long that were claimed and never used. Loved the waterskiing, snorkeling, scuba, Hobie cats and paddle boards, all included. Great beach, can walk forever. Overall we had a great stay, but would not rate it as our all time favorite resort.

Reviewed on Jan 15, 2024

Sandals Montego Bay - ALL INCLUSIVE Couples Only
5.0-star property

Sandals Montego Bay - ALL INCLUSIVE Couples Only

8.6/10 Excellent! (234 reviews)

Sep 8 - Sep 15

7 night stay

Boston (BOS) to Montego Bay (MBJ)

Delta • Non-stop • BusinessClass

Montego Bay (MBJ) to Boston (BOS)

American Airlines • Non-stop • BusinessClass
per person
found 4 hours ago
Great resort. Need more Jamaican food for dinner and breakfast.

Reviewed on Jul 23, 2019

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Middlesex County first class flight packages

Price found within the past 48 hours. Click for updated prices.
Hotel Riu Montego Bay - Adults Only - All Inclusive
4.0-star property

Hotel Riu Montego Bay - Adults Only - All Inclusive

8.4/10 Very Good! (4,760 reviews)

Sep 6 - Sep 13

7 night stay

Boston (BOS) to Montego Bay (MBJ)

American Airlines • Non-stop roundtrip • FirstClass
Save 100% on your flight
per person
found 4 hours ago
I like he close the property is to the airport, and how there’s a grocery store and shopping center across the street. In my opinion, this property lacks in a lot. If you want somewhere to stay that just focuses on partying and having drinking and food available, this is the place for you. However, if you want to be catered to and feel like you’re being spoiled on vacation and have other things to do on the property, this isn’t the place. I was interested in water activities like catamaran or glass bottom boat, but it wasn’t included with the resort. It was available for an additional price, among other things, but that takes away from the “all inclusive” for me. The food was ok. I was only able to secure a reservation for one restaurant in 5 days. The slots fill up quickly. All in all, I enjoyed my stay. I just wanted and expected a little more from the resort based off my previous experiences from other properties in Jamaica.

Reviewed on Jul 24, 2025

The Beach Villas at Excellence Oyster Bay - Adults Only All Inclusive
5.0-star property

The Beach Villas at Excellence Oyster Bay - Adults Only All Inclusive

10/10 Exceptional! (2 reviews)

Sep 6 - Sep 13

7 night stay

Boston (BOS) to Montego Bay (MBJ)

American Airlines • Non-stop roundtrip • FirstClass
per person
found 4 hours ago
Hotel Riu Palace Aquarelle - All Inclusive
4.0-star property

Hotel Riu Palace Aquarelle - All Inclusive

8.8/10 Excellent! (1,550 reviews)

Sep 6 - Sep 13

7 night stay

Boston (BOS) to Montego Bay (MBJ)

American Airlines • Non-stop roundtrip • FirstClass
Save 100% on your flight
per person
found 4 hours ago
Very friendly. Wasn't to happy they didn't offer early check in for a fee.

Reviewed on Aug 1, 2025

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More About Flying To Middlesex County from Boston

Route Information for Flights from Boston to Middlesex County

Origin Airport IATA Code
BOS
Destination Airport IATA Code
KIN
Distance
1697 mi
Direct Flight Airlines
JetBlue
Earliest Flight Arrival
5:30PM UTC
Latest Flight Arrival
5:30PM UTC

Boston to Middlesex County

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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.