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Cheap flights from Worcester, Massachusetts to Caribbean Islands from $238

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Worcester, Massachusetts to Caribbean Islands departing on 8/19. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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0 bags

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Find the cheapest flights from Worcester, Massachusetts to Caribbean Islands

Cheap round-trip flights

American Airlines Logo
3:25 pm - 11:40 pmORH-SJU
7h 15m1 stop
American Airlines Logo
4:50 pm - 2:53 pmSJU-ORH
23h 03m2 stops
$342American Airlines
Find Deal
Sun, Feb 1 - Tue, Feb 17
JetBlue Logo
11:57 am - 8:20 pmORH-SJU
8h 23m1 stop
JetBlue Logo
5:05 am - 2:45 pmSJU-ORH
10h 40m1 stop
$363JetBlue
Find Deal
Thu, Oct 30 - Sun, Nov 2
American Airlines Logo
3:20 pm - 10:49 pmORH-SJU
7h 29m1 stop
American Airlines Logo
8:30 am - 2:55 pmSJU-ORH
6h 25m1 stop
$364American Airlines
Find Deal
Tue, Aug 26 - Fri, Aug 29
American Airlines Logo
3:20 pm - 10:49 pmORH-SJU
7h 29m1 stop
American Airlines Logo
5:35 pm - 2:55 pmSJU-ORH
21h 20m2 stops
$368American Airlines
Find Deal
Tue, Aug 26 - Thu, Aug 28
JetBlue Logo
10:45 am - 8:34 pmORH-SJU
9h 49m1 stop
JetBlue Logo
6:45 am - 3:03 pmSJU-ORH
8h 18m1 stop
$374JetBlue
Find Deal
Wed, Aug 20 - Sun, Aug 24
American Airlines Logo
4:23 pm - 10:30 amORH-MBJ
43h 07m2 stops
American Airlines Logo
1:55 pm - 3:58 pmMBJ-ORH
25h 03m2 stops
$376American Airlines
Find Deal
Fri, Sep 19 - Fri, Sep 26
American Airlines Logo
3:29 pm - 11:07 amORH-NAS
19h 38m2 stops
American Airlines Logo
6:45 pm - 2:53 pmNAS-ORH
20h 08m2 stops
$389American Airlines
Find Deal
Mon, Dec 1 - Fri, Dec 12
American Airlines Logo
3:29 pm - 11:20 amORH-NAS
19h 51m1 stop
American Airlines Logo
6:45 pm - 2:53 pmNAS-ORH
20h 08m2 stops
$391American Airlines
Find Deal
Mon, Dec 1 - Tue, Dec 9
American Airlines Logo
3:29 pm - 11:20 amORH-NAS
19h 51m1 stop
American Airlines Logo
12:10 pm - 2:53 pmNAS-ORH
26h 43m1 stop
$393American Airlines
Find Deal
Sat, Nov 29 - Thu, Dec 11
JetBlue Logo
10:45 am - 8:34 pmORH-SJU
9h 49m1 stop
JetBlue Logo
6:45 am - 3:03 pmSJU-ORH
8h 18m1 stop
$394JetBlue
Find Deal
Fri, Aug 22 - Sun, Aug 24

American Airlines flights from Worcester, Massachusetts to Caribbean Islands

Our best American Airlines deals on Worcester, Massachusetts to Caribbean Islands flight tickets
American Airlines
Feb 1
ORH3:25 pmWorcester
7h 15m
1 stop
SJU11:40 pmSan Juan Luis Munoz Marin Intl
Feb 17
SJU4:50 pmSan Juan Luis Munoz Marin Intl
23h 03m
2 stops
ORH2:53 pmWorcester
$342
Find similar
American Airlines
Aug 26
ORH3:20 pmWorcester
7h 29m
1 stop
SJU10:49 pmSan Juan Luis Munoz Marin Intl
Aug 29
SJU8:30 amSan Juan Luis Munoz Marin Intl
6h 25m
1 stop
ORH2:55 pmWorcester
$364
Find similar
American Airlines
Aug 26
ORH3:20 pmWorcester
7h 29m
1 stop
SJU10:49 pmSan Juan Luis Munoz Marin Intl
Aug 28
SJU5:35 pmSan Juan Luis Munoz Marin Intl
21h 20m
2 stops
ORH2:55 pmWorcester
$368
Find similar

JetBlue flights from Worcester, Massachusetts to Caribbean Islands

Our best JetBlue deals on Worcester, Massachusetts to Caribbean Islands flight tickets
JetBlue
Oct 30
ORH11:57 amWorcester
8h 23m
1 stop
SJU8:20 pmSan Juan Luis Munoz Marin Intl
Nov 2
SJU5:05 amSan Juan Luis Munoz Marin Intl
10h 40m
1 stop
ORH2:45 pmWorcester
$363
Find similar
JetBlue
Aug 20
ORH10:45 amWorcester
9h 49m
1 stop
SJU8:34 pmSan Juan Luis Munoz Marin Intl
Aug 24
SJU6:45 amSan Juan Luis Munoz Marin Intl
8h 18m
1 stop
ORH3:03 pmWorcester
$374
Find similar
JetBlue
Aug 22
ORH10:45 amWorcester
9h 49m
1 stop
SJU8:34 pmSan Juan Luis Munoz Marin Intl
Aug 24
SJU6:45 amSan Juan Luis Munoz Marin Intl
8h 18m
1 stop
ORH3:03 pmWorcester
$394
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Worcester, Massachusetts to Caribbean Islands that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, momondo users made 832,500 searches. Data last updated August 6, 2025.
Use the filters below to find and compare flights from Worcester, Massachusetts to Caribbean Islands that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

WorcesterSan Juan

ORH - SJU

ORHSJU

Worcester

Sun 2/1

3:25 pm-11:40 pm

1 stop7h 15m

San Juan Luis Munoz Marin Intl

Tue 2/17

4:50 pm-2:53 pm

2 stops23h 03m

$342

WorcesterSan Juan

ORH - SJU

ORHSJU

Worcester

Thu 10/30

11:57 am-8:20 pm

1 stop8h 23m

San Juan Luis Munoz Marin Intl

Sun 11/2

5:05 am-2:45 pm

1 stop10h 40m

$363

WorcesterSan Juan

ORH - SJU

ORHSJU

Worcester

Tue 8/26

3:20 pm-10:49 pm

1 stop7h 29m

San Juan Luis Munoz Marin Intl

Fri 8/29

8:30 am-2:55 pm

1 stop6h 25m

$364

WorcesterSan Juan

ORH - SJU

ORHSJU

Worcester

Tue 8/26

3:20 pm-10:49 pm

1 stop7h 29m

San Juan Luis Munoz Marin Intl

Thu 8/28

5:35 pm-2:55 pm

2 stops21h 20m

$368

WorcesterSan Juan

ORH - SJU

ORHSJU

Worcester

Wed 8/20

10:45 am-8:34 pm

1 stop9h 49m

San Juan Luis Munoz Marin Intl

Sun 8/24

6:45 am-3:03 pm

1 stop8h 18m

$374

WorcesterMontego Bay

ORH - MBJ

ORHMBJ

Worcester

Fri 9/19

4:23 pm-10:30 am

2 stops43h 07m

Montego Bay Sangster Intl

Fri 9/26

1:55 pm-3:58 pm

2 stops25h 03m

$376

WorcesterNassau

ORH - NAS

ORHNAS

Worcester

Mon 12/1

3:29 pm-11:07 am

2 stops19h 38m

Nassau Intl

Fri 12/12

6:45 pm-2:53 pm

2 stops20h 08m

$389

WorcesterNassau

ORH - NAS

ORHNAS

Worcester

Mon 12/1

3:29 pm-11:20 am

1 stop19h 51m

Nassau Intl

Tue 12/9

6:45 pm-2:53 pm

2 stops20h 08m

$391

WorcesterNassau

ORH - NAS

ORHNAS

Worcester

Sat 11/29

3:29 pm-11:20 am

1 stop19h 51m

Nassau Intl

Thu 12/11

12:10 pm-2:53 pm

1 stop26h 43m

$393

WorcesterSan Juan

ORH - SJU

ORHSJU

Worcester

Fri 8/22

10:45 am-8:34 pm

1 stop9h 49m

San Juan Luis Munoz Marin Intl

Sun 8/24

6:45 am-3:03 pm

1 stop8h 18m

$394

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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See travel insights to Caribbean Islands from

How to get the cheapest flight ticket from Worcester, Massachusetts to Caribbean Islands

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the cheapest day to depart on your flight to Caribbean Islands?

The cheapest day to depart from Worcester, Massachusetts to Caribbean Islands is on a Wednesday. Travelers who choose to depart for Caribbean Islands on a Wednesday will often find tickets for as low as $210. If your travel schedule is flexible, try to avoid departing on a Saturday because tickets tend to average around $975. These prices are subject to change though, so be sure to set up a Price Alert for flights to Caribbean Islands.

What is the cheapest time of day to depart on your flight to Caribbean Islands?

According to our data, the cheapest time of day to fly to Caribbean Islands is in the morning. momondo users have found flights departing from Worcester, Massachusetts to Caribbean Islands in the morning for as low as $233. Keep in mind that these prices may fluctuate based on what airline you choose and the time of year you plan to travel. Try not to purchase tickets in the afternoon because they tend to be around $1,005. Of course, these prices can vary depending on the time of year and what airport you fly to.

Cheap Worcester, Massachusetts to Caribbean Islands flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Worcester, Massachusetts to Caribbean Islands

Best Price Found

$238

Fastest flight time

6h 45m

Direct flights

None

Airports in Caribbean Islands

6 airports
The best one-way flight to Caribbean Islands from Worcester, Massachusetts in the past 72 hours is $238. The best round-trip flight deal from Worcester, Massachusetts to Caribbean Islands found on momondo in the last 72 hours is $342.
The fastest flight from Worcester, Massachusetts to Caribbean Islands takes 6h 45m
There are no direct flights from Worcester, Massachusetts to Caribbean Islands. Popular non-direct routes for this connection are Worcester Airport - Oranjestad Reina Beatrix Airport, Worcester Airport - Montego Bay Sangster Intl Airport and Worcester Airport - San Juan Luis Munoz Marin Intl Airport.
There are 6 airports near Caribbean Islands: Nassau Intl (NAS), Santo Domingo Las Americas (SDQ), Saint Thomas Island Cyril E King (STT), Montego Bay Sangster Intl (MBJ), Oranjestad Reina Beatrix (AUA), San Juan Luis Munoz Marin Intl (SJU)
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  • When did momondo last update prices for flights from Worcester Airport to Caribbean Islands?

    Prices for flights from Worcester Airport to Caribbean Islands were last updated today.

  • How many operators does momondo search for flights from Worcester Airport to Caribbean Islands?

  • How old do you have to be to fly from Worcester Airport to Caribbean Islands?

    The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Worcester Airport to Caribbean Islands.

  • What documentation or ID do you need to fly to Caribbean Islands?

    The required travel and health documents for your Caribbean Islands trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Caribbean Islands. We recommend that you seek guidance from your airline or a reliable third party such as IATA.

  • What is the most popular plane model from Worcester, Massachusetts to Caribbean Islands?

Best airlines flying from Worcester, Massachusetts to Caribbean Islands

Compare and see reviews for airlines that fly from Worcester, Massachusetts to Caribbean Islands with momondo
Airline
Rating
Free Cancellation
Price
JetBluePriceFrom $136Free CancellationRating
7.2
2,915 reviews
Search JetBlue flights

Why use momondo?

Why should I use momondo to find a flight deal from Worcester to Caribbean Islands?

momondo compares prices from hundreds of airlines and agents so you can find and book the best deal on flights from Worcester to Caribbean Islands. Millions of users trust and use momondo every year so you are in good hands.

Can I find flights from Worcester to Caribbean Islands with flexible booking policies on momondo?

Flights from Worcester to Caribbean Islands with flexible booking policies can be found by using the search form above and then selecting our dedicated flexible booking filter, which will highlight only the flights where this policy is applied.

How can momondo help me find flights from Worcester to Caribbean Islands?

momondo provides multiple filters to help you find the best flight to Caribbean Islands from Worcester. Filter by price, airline, airports, cabin, aircraft, payment method, number of stops and more.

I’m not ready to book a flight from Worcester to Caribbean Islands right now. Can momondo alert me if prices change?

If you are simply researching potential flights to Caribbean Islands, momondo offers a useful price alert feature which will track prices for flights to Caribbean Islands from Worcester and alert you when they change.

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