Puerto Rico — flights from Windsor Locks to Puerto Rico

Flight Deals from Windsor Locks to Puerto Rico from $103

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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
$198	$103	$303	Late Night	Tuesday	4 weeks
Cheapest round-trip found on Priceline in the last 8 days. $169 below the typical $367 round-trip on this route. Lowest one-way found in the last 8 days. The typical one-way fare is $176. A round-trip at or under $303 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 $345 on this route, the lowest of any weekday. $18 less than the average weekday, which is $363. Late Night departures average $241 on this route, the lowest of any time of day. $109 less than the average departure, which is $350. Fares on this route are lowest when booked about 4 weeks before departure. See all flights to San Juan →
$423	$295	$529	Midday	Tuesday	4 weeks
Cheapest round-trip found on Priceline in the last 8 days. $152 below the typical $575 round-trip on this route. Lowest one-way found in the last 8 days. The typical one-way fare is $441. A round-trip at or under $529 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 $553 for flights to this destination, the lowest of any weekday. $30 less than the average weekday, which is $583. Midday departures average $581 on this route, the lowest of any time of day. $32 less than the average departure, which is $613. Fares to this destination are lowest when booked about 4 weeks before departure. See all flights to Aguadilla →
$579	$279	$638	Midday	Tuesday	4 weeks
Cheapest round-trip found on Priceline in the last 8 days. $104 below the typical $683 round-trip on this route. Lowest one-way found in the last 8 days. The typical one-way fare is $479. A round-trip at or under $638 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 $662 for flights to this destination, the lowest of any weekday. $36 less than the average weekday, which is $698. Midday departures average $694 on this route, the lowest of any time of day. $3 less than the average departure, which is $697. Fares to this destination are lowest when booked about 4 weeks before departure. See all flights to Ponce →
$474	$248	$562	Midday	Tuesday	4 weeks
Cheapest round-trip found on Priceline in the last 8 days. $108 below the typical $582 round-trip on this route. Lowest one-way found in the last 8 days. The typical one-way fare is $376. A round-trip at or under $562 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 $586 for flights to this destination, the lowest of any weekday. $32 less than the average weekday, which is $618. Midday departures average $585 on this route, the lowest of any time of day. $49 less than the average departure, which is $634. Fares to this destination are lowest when booked about 4 weeks before departure. See all flights to Mayagueez →
$564	$282	$682	Evening	Tuesday	4 weeks
Cheapest round-trip found on Priceline in the last 8 days. $238 below the typical $802 round-trip on this route. Lowest one-way found in the last 8 days. The typical one-way fare is $462. A round-trip at or under $682 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 $710 for flights to this destination, the lowest of any weekday. $38 less than the average weekday, which is $748. Evening departures average $708 on this route, the lowest of any time of day. $69 less than the average departure, which is $777. Fares to this destination are lowest when booked about 4 weeks before departure. See all flights to Culebra →

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 Puerto Rico Hotel + Flight Packages

Holiday Inn Express San Juan Condado By IHG

Round-trip flight from Windsor Locks

BDL to SJU

Holiday Inn Express San Juan Condado By IHG

San Juan, 1 Calle Mariano Ramirez Bages

7.9585 Reviews3.5-Star Hotel

19% Package Savings

^$1,039/person

$2,577 $2,077 total

Incl. Flight + Hotel

Round-trip flight from Windsor Locks

BDL to BQN

Pasavento - Modern Tiny Suite

Aguadilla, Avenida Severiano Cuevas Pasavento Modern Suites Ii

9.239 Reviews0-Star Hotel

^$824/person

$1,647 total

Incl. Flight + Hotel

Round-trip flight from Windsor Locks

BDL to MAZ

TRYP by Wyndham Mayaguez

Mayaguez, 11 Calle Santiago Riera Palmer

8.7557 Reviews3-Star Hotel

11% Package Savings

^$851/person

$1,905 $1,701 total

Incl. Flight + Hotel

Round-trip flight from Windsor Locks

BDL to BQN

Modern Suite #0 - best location

Aguadilla, Avenida Doctor Pedro Albizu Campos Edificio Pasavento

9.1112 Reviews0-Star Hotel

^$894/person

$1,787 total

Incl. Flight + Hotel

Round-trip flight from Windsor Locks

BDL to PSE

Savvys Place

Ponce, 72 Calle Vives 3

9.215 Reviews0-Star Hotel

^$1,037/person

$2,074 total

Incl. Flight + Hotel

Round-trip flight from Windsor Locks

BDL to MAZ

pineapple hospitality

Mayaguez, Calle Santiago Riera Palmer

9.546 Reviews0-Star Hotel

^$887/person

$1,774 total

Incl. Flight + Hotel

Best Puerto Rico Hotel + Flight + Car Packages

Round-trip flight from Windsor Locks

BDL to CPX

Always Summer Inn Bay Front

Culebra, Calle 5 La Romana

8.510 Reviews0-Star Hotel

Rental car included

Pick-up in CPX

^$1,090/person

$2,179 total

Incl. Flight + Hotel + Car

Round-trip flight from Windsor Locks

BDL to SJU

Hyatt House San Juan

San Juan, 615 Ave Distrito De Convenciones

8.7565 Reviews3.5-Star Hotel

Rental car included

Pick-up in SJU

16% Package Savings

^$1,268/person

$3,005 $2,535 total

Incl. Flight + Hotel + Car

Round-trip flight from Windsor Locks

BDL to BQN

Modern Suite #0 - best location

Aguadilla, Avenida Doctor Pedro Albizu Campos Edificio Pasavento

9.1112 Reviews0-Star Hotel

Rental car included

Pick-up in BQN

^$940/person

$1,880 total

Incl. Flight + Hotel + Car

Round-trip flight from Windsor Locks

BDL to MAZ

pineapple hospitality

Mayaguez, Calle Santiago Riera Palmer

9.546 Reviews0-Star Hotel

Rental car included

Pick-up in MAZ

^$938/person

$1,876 total

Incl. Flight + Hotel + Car

Round-trip flight from Windsor Locks

BDL to CPX

Casa Robinson Guest House

Culebra, H-10 Bo. La Romana Po Box 244

8.386 Reviews3-Star Hotel

Rental car included

Pick-up in CPX

^$1,131/person

$2,261 total

Incl. Flight + Hotel + Car

Round-trip flight from Windsor Locks

BDL to SJU

Holiday Inn Express San Juan Condado By IHG

San Juan, 1 Calle Mariano Ramirez Bages

7.9585 Reviews3.5-Star Hotel

Rental car included

Pick-up in SJU

13% Package Savings

^$1,092/person

$2,516 $2,184 total

Incl. Flight + Hotel + Car

Round-trip flight from Windsor Locks

BDL to BQN

Pasavento - Modern Tiny Suite

Aguadilla, Avenida Severiano Cuevas Pasavento Modern Suites Ii

9.239 Reviews0-Star Hotel

Rental car included

Pick-up in BQN

^$870/person

$1,740 total

Incl. Flight + Hotel + Car

Round-trip flight from Windsor Locks

BDL to MAZ

TRYP by Wyndham Mayaguez

Mayaguez, 11 Calle Santiago Riera Palmer

8.7557 Reviews3-Star Hotel

Rental car included

Pick-up in MAZ

10% Package Savings

^$902/person

$2,013 $1,803 total

Incl. Flight + Hotel + Car

When is the cheapest time to fly?

Cheapest in late January at about $470

Fares from Windsor Locks to Puerto Rico are lowest in late January, around $470, and January is the cheapest month overall, averaging $487. They peak in early July at about $702, $232 more than the low. The yearly average is $592.

Show the data

When is the cheapest time to fly?
Month	Average fare	Early month	Late month
January	$487	$505	$470
February	$570	$537	$608
March	$600	$592	$607
April	$633	$653	$614
May	$597	$572	$620
June	$671	$640	$701
July	$683	$702	$664
August	$576	$609	$544
September	$547	$541	$553
October	$543	$552	$534
November	$564	$566	$563
December	$629	$556	$697

How far in advance should I book?

Cheapest about 4 weeks out at $543

Book about 4 weeks before departure for the best fares from Windsor Locks to Puerto Rico, around $543. Booking in the final days before the flight costs about $691, $148 more. Booking six months ahead runs about $857.

Show the data

How far in advance should I book? (selected points, lowest and highest included)
Days before departure	Average fare
180 days	$857
172 days	$853
164 days	$886
163 days	$888
156 days	$865
148 days	$815
140 days	$786
132 days	$762
124 days	$745
116 days	$705
108 days	$657
100 days	$629
92 days	$617
84 days	$612
76 days	$598
68 days	$579
2mo	$560
52 days	$550
44 days	$557
36 days	$560
28 days	$545
26 days	$543
20 days	$545
12 days	$583
4 days	$655
0 days	$691

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

Tuesday is the cheapest day of the week to fly from Windsor Locks to Puerto Rico. At $585 it is 5% cheaper than the average day. Friday is the most expensive day, 4% above average.

Show the data

What's the cheapest day of the week to fly?
Day	Average fare
Sun	$604
Mon	$625
Tue	$585
Wed	$606
Thu	$618
Fri	$639
Sat	$613

When is the best time of day to fly?

Late night (9pm - 12am) is the cheapest time of day to fly from Windsor Locks to Puerto Rico. At $241 it is 53% cheaper than the average time. Midday (12pm - 2pm) is the most expensive time, 26% above average.

Show the data

When is the best time of day to fly?
Time of day	Average fare
Morning	$636
Midday	$651
Afternoon	$482
Evening	$571
Late Night	$241

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

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

Show the data

What do round-trip flights from Windsor Locks to Puerto Rico cost?
Price range	Share of fares
$250 to $500	14%
$500 to $750	28%
$750 to $1,000	28%
$1,000 to $1,250	18%
$1,250 to $1,500	8%
$1,500 to $1,750	4%
$1,750 and up	1%

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 Puerto Rico 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 Puerto Rico.

When is the cheapest time to fly from Windsor Locks to Puerto Rico?

The cheapest months to fly from Windsor Locks to Puerto Rico are January, September, and October, with January running 15% below the yearly average and a half-month low in late January. The priciest months are July and June, at 15% and 12% above the yearly average respectively, with late December the most expensive half-month. These figures come from the Hartford to San Juan pair.

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 Puerto Rico?

The best booking window for flights from Windsor Locks to Puerto Rico is 20 to 40 days before departure, with the lowest fares appearing around 25 days out. Fares do rise when booking very early, as the priciest lead time is 160 days. These figures come from the Hartford–San Juan city pair.

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 Puerto Rico?

In Puerto Rico, most travelers fly into San Juan for Old San Juan, Condado and Isla Verde. Popular add-ons include the beaches and bioluminescent bay in Vieques, the surf and laid-back vibe of Rincón, the food scene in Ponce and the rainforest and outdoor activities around Fajardo and Luquillo.

When is the best time of year to visit Puerto Rico?

For Puerto Rico, mid-December through April is the driest, most comfortable season, especially for San Juan and the beaches, though late December to early April is peak pricing. May to June and November offer lower fares and lighter crowds before and after the summer rush.

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

Getting to Bradley International Airport from downtown Hartford is easiest via the CTtransit 30-Bradley Flyer bus, which runs semi-express between Union Station and the Connecticut Convention Center and the airport, making it the most popular public option. Ride-share services like Uber and Lyft are authorized at BDL and pick up outside door 2 on the arrivals level, typically arriving within 3-5 minutes of request; taxis are also available on demand at the curb outside doors 2 and 3, with prearranged fares to downtown starting around $45. Driving and parking is straightforward via I-91 Exit 40, with a range of garage, long-term, and economy lots, though the closest options can fill up on busy days, so a shuttle from a nearby lot may be needed. A taxi or ride-share is generally the fastest door-to-door option, while the bus is the most budget-friendly.

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 Puerto Rico from $103

Good to Know

Best Puerto Rico Hotel + Flight Packages

Best Puerto Rico 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 Puerto Rico cost?

Frequently Asked Questions

When is the cheapest time to fly from Windsor Locks to Puerto Rico?

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

What are the most popular cities to visit in Puerto Rico?

When is the best time of year to visit Puerto Rico?

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

Flights to Puerto Rico