Jamaica — flights from Windsor Locks to Jamaica

Flight Deals from Windsor Locks to Jamaica from $203

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Good to Know

Cheapest fares and when to fly, by destination city — select a row for the details.

Cheapest RT	Cheapest OW	Good Deal Price	Best Time to Fly	Best Day to Fly	When to Book
$429	$203	$462	Afternoon	Tuesday	6 weeks
Cheapest round-trip found on Priceline in the last 8 days. $94 below the typical $523 round-trip on this route. Lowest one-way found in the last 8 days. The typical one-way fare is $443. A round-trip at or under $462 is a good deal on this route right now. 75% of the fares we found cost more; only a quarter cost less. Tuesday departures average $504 on this route, the lowest of any weekday. $29 less than the average weekday, which is $533. Afternoon departures average $484 on this route, the lowest of any time of day. $27 less than the average departure, which is $511. Fares on this route are lowest when booked about 6 weeks before departure. See all flights to Montego Bay →
$550	$241	$662	Afternoon	Wednesday	6 weeks
Cheapest round-trip found on Priceline in the last 8 days. $204 below the typical $754 round-trip on this route. Lowest one-way found in the last 8 days. The typical one-way fare is $414. A round-trip at or under $662 is a good deal on this route right now. 75% of the fares we found cost more; only a quarter cost less. Wednesday departures average $693 on this route, the lowest of any weekday. $94 less than the average weekday, which is $787. Afternoon departures average $742 on this route, the lowest of any time of day. $169 less than the average departure, which is $911. Fares on this route are lowest when booked about 6 weeks before departure. See all flights to Kingston →
$641	$435	$759	Morning	Tuesday	6 weeks
Cheapest round-trip found on Priceline in the last 8 days. $181 below the typical $822 round-trip on this route. Lowest one-way found in the last 8 days. The typical one-way fare is $440. A round-trip at or under $759 is a good deal on this route right now. 75% of the fares we found cost more; only a quarter cost less. Tuesday departures average $797 for flights to this destination, the lowest of any weekday. $47 less than the average weekday, which is $844. Morning departures average $794 on this route, the lowest of any time of day. $45 less than the average departure, which is $839. Fares to this destination are lowest when booked about 6 weeks before departure. See all flights to Ocho Rios →

Methodology: learn how we calculate these figures

The best day to fly and how far ahead to book shown in this table are built from the prices Priceline customers actually paid for flights to this destination over the past 12 months or more.

Where a route has too few bookings to fill a figure, we borrow the shape from a group of routes with similar price behavior and fit it to the fares booked on that route.

Because past fares don’t reflect today’s market, we then adjust the historical prices for current conditions such as inflation and fuel costs, using the round-trip fares found in recent searches.

The cheapest round-trip and one-way fares, the good-deal price and the best time of day to fly come directly from the fares found in recent searches, not from historical bookings.

Best Jamaica Hotel + Flight Packages

Round-trip flight from Windsor Locks

BDL to MBJ

Castlevue B&B

Montego Bay, 6 Sunrise Close

8142 Reviews5-Star Hotel

^$827/person

$1,653 total

Incl. Flight + Hotel

Round-trip flight from Windsor Locks

BDL to OCJ

Galina Breeze

Port Maria, Main Road

8.520 Reviews0-Star Hotel

^$1,223/person

$2,446 total

Incl. Flight + Hotel

Round-trip flight from Windsor Locks

BDL to MBJ

HOTEL GRAND A VIEW

Montego Bay, 3 Ramparts Close

8.1204 Reviews3.5-Star Hotel

13% Package Savings

^$984/person

$2,258 $1,968 total

Incl. Flight + Hotel

Round-trip flight from Windsor Locks

BDL to OCJ

Riu Ocho Rios - All Inclusive

Ocho Rios, P.O. Box 4442

7.6135 Reviews4-Star Hotel

10% Package Savings

^$1,481/person

$3,299 $2,961 total

Incl. Flight + Hotel

Round-trip flight from Windsor Locks

BDL to MBJ

Coyaba Beach Resort

Montego Bay, Ironshore Main Road, Montego Bay

4-Star Hotel

16% Package Savings

^$1,013/person

$2,408 $2,026 total

Incl. Flight + Hotel

Bahia Principe Luxury Runaway Bay - Adults Only All Inclusive

Round-trip flight from Windsor Locks

BDL to OCJ

Bahia Principe Luxury Runaway Bay - Adults Only All Inclusive

Runaway Bay, Salt Coppers, Runaway Bay

8.2249 Reviews4.5-Star Hotel

10% Package Savings

^$1,762/person

$3,899 $3,523 total

Incl. Flight + Hotel

Best Jamaica Hotel + Flight + Car Packages

Round-trip flight from Windsor Locks

BDL to KIN

Kingston Airport bed and breakfast

Kingston, 14 Fernandez Avenue

6.131 Reviews0-Star Hotel

Rental car included

Pick-up in KIN

^$940/person

$1,880 total

Incl. Flight + Hotel + Car

Round-trip flight from Windsor Locks

BDL to KIN

Chillinn at Duke

Kingston, 66 Duke Street

9.1183 Reviews0-Star Hotel

Rental car included

Pick-up in KIN

^$1,013/person

$2,025 total

Incl. Flight + Hotel + Car

Round-trip flight from Windsor Locks

BDL to OCJ

Riu Ocho Rios - All Inclusive

Ocho Rios, P.O. Box 4442

7.6135 Reviews4-Star Hotel

Rental car included

Pick-up in OCJ

9% Package Savings

^$1,626/person

$3,592 $3,252 total

Incl. Flight + Hotel + Car

Round-trip flight from Windsor Locks

BDL to MBJ

Coyaba Beach Resort

Montego Bay, Ironshore Main Road, Montego Bay

4-Star Hotel

Rental car included

Pick-up in MBJ

15% Package Savings

^$1,110/person

$2,601 $2,219 total

Incl. Flight + Hotel + Car

Round-trip flight from Windsor Locks

BDL to KIN

Captain Morgan House

Kingston, Outlook Avenue

0-Star Hotel

Rental car included

Pick-up in KIN

^$1,119/person

$2,237 total

Incl. Flight + Hotel + Car

Round-trip flight from Windsor Locks

BDL to OCJ

Bahia Principe Luxury Runaway Bay - Adults Only All Inclusive

Runaway Bay, Salt Coppers, Runaway Bay

8.2249 Reviews4.5-Star Hotel

Rental car included

Pick-up in OCJ

9% Package Savings

^$1,906/person

$4,191 $3,811 total

Incl. Flight + Hotel + Car

Round-trip flight from Windsor Locks

BDL to MBJ

Castlevue B&B

Montego Bay, 6 Sunrise Close

8142 Reviews5-Star Hotel

Rental car included

Pick-up in MBJ

^$926/person

$1,852 total

Incl. Flight + Hotel + Car

Round-trip flight from Windsor Locks

BDL to OCJ

Galina Breeze

Port Maria, Main Road

8.520 Reviews0-Star Hotel

Rental car included

Pick-up in OCJ

^$1,362/person

$2,724 total

Incl. Flight + Hotel + Car

Round-trip flight from Windsor Locks

BDL to MBJ

HOTEL GRAND A VIEW

Montego Bay, 3 Ramparts Close

8.1204 Reviews3.5-Star Hotel

Rental car included

Pick-up in MBJ

12% Package Savings

^$1,080/person

$2,453 $2,159 total

Incl. Flight + Hotel + Car

When is the cheapest time to fly?

Cheapest in late September at about $548

Fares from Windsor Locks to Jamaica are lowest in late September, around $548, and September is the cheapest month overall, averaging $560. They peak in late December at about $753, $205 more than the low. The yearly average is $627.

Show the data

When is the cheapest time to fly?
Month	Average fare	Early month	Late month
January	$591	$617	$567
February	$594	$581	$608
March	$637	$623	$650
April	$627	$646	$609
May	$604	$591	$617
June	$668	$643	$694
July	$697	$702	$692
August	$654	$676	$633
September	$560	$572	$548
October	$572	$563	$580
November	$617	$606	$628
December	$707	$657	$753

How far in advance should I book?

Cheapest about 5 weeks out at $572

Book about 5 weeks before departure for the best fares from Windsor Locks to Jamaica, around $572. Booking in the final days before the flight costs about $668, $96 more. Booking six months ahead runs about $779.

Show the data

How far in advance should I book? (selected points, lowest and highest included)
Days before departure	Average fare
180 days	$779
172 days	$785
164 days	$793
162 days	$795
156 days	$795
148 days	$783
140 days	$757
132 days	$729
124 days	$708
116 days	$690
108 days	$676
100 days	$662
92 days	$644
84 days	$624
76 days	$606
68 days	$592
2mo	$584
52 days	$578
44 days	$576
36 days	$572
28 days	$574
20 days	$590
12 days	$622
4 days	$656
0 days	$668

What's the cheapest day of the week to fly?

Wednesday is the cheapest day of the week to fly from Windsor Locks to Jamaica. At $686 it is 5% cheaper than the average day. Friday is the most expensive day, 6% above average.

Show the data

What's the cheapest day of the week to fly?
Day	Average fare
Sun	$722
Mon	$700
Tue	$690
Wed	$686
Thu	$762
Fri	$771
Sat	$743

When is the best time of day to fly?

Morning (5am - 12pm) is the cheapest time of day to fly from Windsor Locks to Jamaica. At $682 it is 13% cheaper than the average time. Midday (12pm - 2pm) is the most expensive time, 17% above average.

Show the data

When is the best time of day to fly?
Time of day	Average fare
Morning	$682
Midday	$910
Afternoon	$703
Evening	$828

What do round-trip flights from Windsor Locks to Jamaica cost?

Share of fares in each price range, adjusted to current prices.

Show the data

What do round-trip flights from Windsor Locks to Jamaica cost?
Price range	Share of fares
$0 to $400	13%
$400 to $800	37%
$800 to $1,200	27%
$1,200 to $1,600	12%
$1,600 to $2,000	7%
$2,000 to $2,400	2%
$2,400 and up	2%

Methodology: learn how we calculate these charts

The charts “When is the cheapest time to fly?”, “How far in advance should I book?”, “What's the cheapest day of the week to fly?” and “What do round-trip flights from Windsor Locks to Jamaica cost?” are built from the prices Priceline customers actually paid for flights on this route over the past 12 months or more.

Where a route has too few bookings to fill every point in a chart, we borrow the shape of the curve from a group of routes with similar price behavior and fit it to the fares booked on this route.

Because past fares don’t reflect today’s market, we then adjust the historical prices for current conditions such as inflation and fuel costs, using the round-trip fares found in recent searches on this route.

The chart “When is the best time of day to fly?” is calculated directly from the fares found in recent searches, not from historical bookings.

Frequently Asked Questions

Everything you need to know about flying from Windsor Locks to Jamaica.

When is the cheapest time to fly from Windsor Locks to Jamaica?

The cheapest months to fly from Windsor Locks to Jamaica are September, October, and January, with the very lowest fares found in late September. The priciest months are December and July, with late December standing out as the single most expensive period. These figures come from the busiest gateway pairs between Hartford and Montego Bay and Kingston.

Methodology

These seasonal fares look at the busiest city-to-city routes between the two places (up to four, chosen by scheduled flights) and at the seasonal fare curve Priceline's own archive provides for each route. Months are ranked by how far each month's average fare sits above or below that route's yearly average, taking the middle value across the routes, so one expensive route cannot dominate.

How far in advance should I book flights from Windsor Locks to Jamaica?

For flights from Windsor Locks to Jamaica, you should book about 4 weeks before departure to get the best fares. This holds for the main city pairs to Montego Bay and Kingston, where booking much earlier than that window pushes fares higher.

Methodology

This booking-window guidance looks at the busiest city-to-city routes between the two places (up to four, chosen by scheduled flights) and at the booking-window fare curve Priceline's own archive provides for each route. The best time to book is the middle value of those routes' cheapest lead times.

What are the most popular cities to visit in Jamaica?

In Jamaica, most travelers fly into Montego Bay for its beaches, all-inclusive resorts and easy access to Negril and Ocho Rios. Kingston is the cultural and business hub, with museums and music history. Negril draws visitors for Seven Mile Beach and cliff diving, while Ocho Rios offers Dunn's River Falls and nearby attractions.

When is the best time of year to visit Jamaica?

Jamaica is warm year round, but the best balance of good weather and fair prices is from mid December to mid April. Summer from June to August is hot, humid and busy in Montego Bay, Ocho Rios and Negril, while September and October bring the highest hurricane risk and the lowest crowds. Late April through May and November offer lighter crowds and lower fares before and after the peak winter season.

How do I get to Bradley Intl Airport from the city center?

From downtown Hartford, the most direct and popular way to reach Bradley International Airport is the CTtransit 30-Bradley Flyer bus, which runs semi-express service from the Connecticut Convention Center and Union Station to the terminal. Prearranged taxis and ride-share services like Uber and Lyft offer faster door-to-door travel, while Route 24 bus connects the airport to the nearby Windsor Locks train station for rail access via the Hartford Line. Driving is straightforward via I-91, with garage, long-term, and economy parking available at the airport, though parking lots can fill up on busy travel days. Taxis and ride-share are typically the fastest option but cost more than the bus, which remains the most economical choice.

References

Public Transportation To/From BDL | Bradley International Airportbradleyairport.com · Published Mar 13, 2026
Bradley International Airport [BDL]: Ultimate Terminal Guideupgradedpoints.com · Published Feb 21, 2026
Bradley Airport Taxi & Car Service | Bradley International Airportbradleyairport.com · Published Jul 14, 2026
Bradley International Airport (BDL) Guide: Tips, Parking, and Travel Infotheparkingspot.com · Published Dec 2, 2024
A Guide to Bradley International Airport (BDL) | Chasechase.com
Car Service to Bradley Airport - GO Airport Shuttle Connecticut2theairport.com · Published Feb 25, 2026
How to get from Bradley Airport (BDL) to Hartford, CT | Uberuber.com · Published Sep 16, 2026
Flights to and from Bradley International Airport BDL | Tickets & Departures - Omioomio.co.uk · Published May 5, 2026

Flight Deals from Windsor Locks to Jamaica from $203

Good to Know

Best Jamaica Hotel + Flight Packages

Best Jamaica Hotel + Flight + Car Packages

When is the cheapest time to fly?

How far in advance should I book?

What's the cheapest day of the week to fly?

When is the best time of day to fly?

What do round-trip flights from Windsor Locks to Jamaica cost?

Frequently Asked Questions

When is the cheapest time to fly from Windsor Locks to Jamaica?

How far in advance should I book flights from Windsor Locks to Jamaica?

What are the most popular cities to visit in Jamaica?

When is the best time of year to visit Jamaica?

How do I get to Bradley Intl Airport from the city center?

Flights to Jamaica