Find cheap flights from Worcester to Caribbean

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ORH — Caribbean
Jul 30 — Aug 61
Round-trip
1 adult
Economy
0 bags
From?
To?
Sat 7/30
Sat 8/6

Good to know

Low season

November

High season

March

Average price round-trip

$668

Good deal round-trip

$432

Good deal one-way

$187
Best time to beat the crowds with an average 3% drop in price.
Most popular time to fly with an average 9% increase in price.
(avg. price over the last 2 weeks)
or less
or less

Top tips for finding cheap flights to Caribbean

  • Looking for a cheap flight? 25% of our users found tickets from Worcester to Caribbean for the following prices or less: to Santo Domingo $187 one-way - $489 round-trip
  • Book at least 2 weeks before departure in order to get a below-average price.
  • High season is considered to be June and July. The cheapest month to fly to Caribbean is January.
  • Morning departure is around 10% more expensive than an evening flight, on average*.
*Average of the lowest prices shown in KAYAK’s search results for departures within the next 30 days

FAQs - booking Caribbean flights

Top airlines flying Worcester to Caribbean

Scores according to KAYAK customer reviews
8.1
JetBlueOverall score based on 20266 reviews
8.2Boarding
8.2Comfort
8.6Crew
7.9Entertainment
7.8Food
Airline reviews
Pros: "Yes"
Cons: "Everything was perfect"
Read more about JetBlue
Pros: "Yes"
Cons: "Everything was perfect"
Cons: "Flight was delayed for 3 hrs"
Cons: "My seat’s tv wasn’t working. Also, controls on the seat for radio, channels, etc. didn’t work."
Pros: "Flight left quick and everything was in order"
Cons: "Food"
Pros: "Crew. Friendly and helpful."
Cons: "Comfortable seats"
Pros: "The movies on plane"
Cons: "Everything else- the flight was delayed 6 hours to my trip and 3 hours from my trip."
Pros: "The crew"
Cons: "Everything good"
Pros: "Yes"
Cons: "Exelente"
Cons: "On time and very comfortable"
Pros: "Swift professional service. Pilot was exceptional; we didn’t even feel the landing or take off"
Cons: "N/a"
Cons: "Flight was late more than 7 hours with no credible explanation"
Pros: "Crew was very polite and accommodating"
Cons: "Flight was delayed 4 times. We had to cancel other reservations and wasted a day traveling instead of a quick 4 hr plane ride."
Cons: "Our flight was delayed an hour"
Pros: "Very good experience with Jetblue’s Crew, comfortable."
Cons: "Food is not something to crave for, 4 hours trip I had to buy a sandwich because the only included is chips and basic beverages. Definitely need to improve."
Cons: "We had to wait 30 minutes for a crew member to show up which delayed our flight."
Pros: "Nothing! The flight was delayed until 10:34pm and still we did not board the plane at that time. Then when we finally board the plane a crew member Dan told me my luggage was to big which it was not, and when we landed in Puerto Rico I had to wait so long to get my luggage from the carousel."
Pros: "Crew was nice, very comfortable flight."
Cons: "The boarding process"
Pros: "The crew was great. We left on time & arrived a few mins early"
Cons: "I guess boarding and disembarking. Since there’s only 1 door used it’s time consuming. Some international carriers do both front and back boarding & disembarking."
Cons: "The flight was delayed for like an hour"
Pros: "Decent airfare and a standard domestic flight. Nothing to complain about. Stewardess was super friendly."
Cons: "Nothing really comes to mind. Everything was fine."
Pros: "How calm the staff remained in the face of many very tired and disappointed people"
Cons: "The flight had a mechanical issue but no mechanic was duty. the flight was supposed to leave at 5, we left at midnight on a plane flown up from Boston. We arrived at 3 in the morning which left me at 61 driving an hour home at a terrible time of night. I was afraid for my safety driving at that hour but they strung us along for so long there were no real opportunities to choose another option. Besides which my bag was stuck in the broken compartment and could not be retrieved. The flight, when it finally left was so cold that everyone was huddled down in their seats, the very senior lade next to me was pitiful. All in all a horrible experience."
Cons: "First i did check in snd told everybody that st that time 3 hours before flight they can't check the Luggage so de has to wait 20 minutes more and do the line again y just to check in the Luggage having already the boarding pass,then they change the gate 2 times and nobody knew where to go and no representive or notification there for half hour y before boarding time."
Cons: "Can’t have a free bag under the plane."
Pros: "The bumped me from my confirmed flight and sent my bsggage on another flight. The JB staff were rude."
Cons: "Television was out due to out of coverage"
Pros: "Short flight. Free movie was good."
Cons: "Flight attendant Christina (New York crew) did not like that I changed my mind about voluntarily checking my suitcase as there was plenty of room in the overhead compartment when I boarded. She said that the only reason I found room was because, by volunteering to check my bag, I was allowed early boarding. I corrected her by telling her that, no, I boarded early because I paid US$45 for an Extra Space seat. She made a face gesture and rolled her eyes. Very childish and unprofessional. She also seemed to have trouble reading the instructions clearly."
Pros: "They were super attentive !"
Pros: "Nothing. I didn’t get to fly and service are check in area was a disaster."
Cons: "On the itinerary my last name was missing an o and they did allow for a name correction."
Pros: "Just two members of the crew in my entire trip were very responsive and attentive with people during the flight Angel and Roberto."
Cons: "Aside Angel and Roberto from the crew, everything else was a disaster with this flight to New York and specifically with JetBlue. Always on delays with every single flight that I had take before, crew personal with a bad attitude and a non effective communication with other passangers. We even lost our first flight returning to our destination because of a misunderstanding with a passanger and one crew member, they made all the passanger to get out of the airplane, after being inside for an hour, then they told us that we lost the flight and they will accommodate us in other flights. We were left there without no hotels, and returning flights with absurd hours of flight and stop, instead of one as before direct to our destination. They report the incident as if it was a weather issue and JetBlue didn’t gave accommodation to all the passanger because of the supposedly reason of weather conditions, and in that manner they don’t provide hotels. By phone I changed my flight to next day and a direct flight back home, but at the counter at the airport they were very mean and with no ways to attend passangers."
Cons: "If the flight is to be delayed, the airline should notify the full delay at once , so people may have a chance to delay arriving to the airport. Additionally when the delay is over 2 hrs they should allow rebooking without penalty, because for some people the trip becalmed useless that particular day because the delay caused the to miss their reasons for flying that day"
Pros: "Comfortable seat, friendly service.The flight was also delayed due to a wing that needed to be repaired before take off. Pilot apologised and stressed that safety comes first."
Cons: "Flight was crowded. Some senior citizens were making "funny" jokes about the wing that was repaired. These jokes were not only not funny, they were making them at the top of their lungs as if they shouting to someone miles away. There were some passengers travelling with pre-teen children also speaking so loudly, it was more like shouting."
Cons: "Almost all JetBlue employees I encountered were rude - yes I know they were frustrated with flight delays because of system failure, but at least y’all are paid. The terminal was dirty, crowded, and everything was shutting down even though people we still looking for food, beverages, Etc (so passengers make sure you are fed / prepared if you’re flying late out of Newark). There was miscommunication from almost every step and even on the play, delays were not conveyed. I’ll definitely avoid booking this flight with the airline & airport moving forward."
Pros: "I didn’t die."
Cons: "The 6 hour delay. The over tired, but outright rude crew in both the airport and plane."
Pros: "Comfortable leg room"
Cons: "On the way to San Juan my flight was delayed for over three hours due to a failure with the heating and cooling system. On the way back to NYC, the flight was delayed for unknown reasons."
Cons: "Low variety of food and the fact that you have to pay for blankets, pillows and head sets"
Pros: "The service"
Cons: "N/A"
Cons: "Service!!!!"
Pros: "Our experience leaving tampa to San juan was absolutely perfect! We were starting our honeymoon and as a courtsey, the attendant who checked us in, was absolutely so sweet. She even upgarded us to even more space seats at no extra charge."
Cons: "The flight back to tampa from san juan was a complete nightmare! We arrived at the gate 15 minutes before and was extremely upset to find out that the gates were closed. The pilot and the attendants saw that we were banging on the door and yet they just stared at us. The plane wasnt detached from the terminal which is why I didnt understand why they couldnt let me in unless they sold my seat. An attendant finally came out by the name of Chanel (the AD Lead). All she did is rebook me for 2 days later and told me that that flight might get cancelled due to the hurricane. She wasn't even trying at all to help me. She had a rude attitude and told me that she will be back to help me. Yeah right! She came back 3 hours later! I could not stand to even look at this unprofessional employee. I paid extra to fly jetblue as I have been told they have great customer service. Pshhhh.... I myself had to call jetblue and spoke to melinda (customer service supervisor) she was trying everything in her power and it really showed. An attendant came and started checking the next flight out of puerto rico to ft. Lauderdale. Melinda put me on stand by for the flight and ecen spoke directly to the Natalie who was checking guests on the flight. Two seats came available for me and my husband to get back to florida. We then rented a car and drove 4 hours back to tampa. I was just completely disgusted on how Chanel handled the whole situation. I told her that I had medical treatments the next morning in tanpa that I could not miss but yet she did not at all seem to care. As a lead I thought she would at least put me on stand by to go to ft. Lauderdale. That wasnt even an option for Chanel. She was completely worthless and had a stupid look on her face when she saw me get on the plane to fy. Lauderdale. Something she could have helped me with instead of saying she would be right back and left me for 3 hours later with no help. Jetblue, I say this in the kindest of ways, please fire chanel. People like that will only cost you guys more in the future as you will loose so much clientel due to the unprofessional conduct and customer service she gave. Hire more Natalie's and Melindas who help you regardless of the situation and not Chanel who didnt care and was a bother to her to put in the same type of customer service that Melinda and Natalie gave me."
Cons: "It was cold. Regulating temperature would be nice"
Pros: "Nothing."
Cons: "The flight was delayed, boarding was slow, you could not here the representative over the loudspeaker. Chairs were tight, very little room. They did not even give anything complimentary for the delay."
Pros: "The"
Cons: "The front desk at St. Croix USVI was very unprofessional. They were dancing at the counter, could not clearly understand their announcement, and they were having side conversations at the counter in front of passengers."
Pros: "Conscience and timing"
Cons: "Tv, internet did not work majority of the flight, air was not that high."
Pros: "Very good"
Pros: "Rapido"
Cons: "Avion pequeño"
Cons: "Long security lines; contradictory agent instructions; couldn't pick seat; flight delayed three times; Uncomfortable seats."
Pros: "This trip from Orlando to San Juan had a swift boarding process"
Cons: "Due to the Orlando airport that was upgrading the tram we had a additional travel time to the terminal"
Pros: "Yes"

Traveled in business class and all they offered, besides liquor, wine and other refreshment, were chips and cookies...really?!

Just perfect

For a delayed flight, and one that most choose because of the amenities, no one apologized for the lack of amenities. A simple, “we are truly sorry” announced to everyone would have gone miles. Instead, the crew kept trying to almost conceal the total lack of available entertainment and even feign like it might “sort of work” until the last minute. I was traveling with my life partner, who intended upon and did work the whole flight (despite zero internet, even for the little time avail that we are aware of when traveling to/from PR), but also with a just turned 6 year old who had been looking forward to using “his own” screen for the last 2 weeks. Underwhelming to say the least. The crew’s apathy didn’t help.

Cons: "Some of the crew had an attitude and the purchased WiFi did not work"
Cons: "Almost 4 hour delay."
Pros: "Everything"
Cons: "It’s perfect"
Cons: "Staff at Pensacola airport not very helpful or friendly."
Pros: "Crew was snappy in getting people in plane and checking in carry ons since occupancy had been reached."
Cons: "Lack of adjustable headrest on seat."
Pros: "Crew helped us find new seats on board."
Cons: "American Airlines changed our seats after ticket purchase so that we were not sitting together. We chose seats at check-in in San Francisco so that we could sit together. When we landed in Miami we discovered our seats had been changed yet again and we were seated in different rows, middle seat!"
Pros: "Smooth ride"
Cons: "Feeling of being cramped"
Pros: "Crew was great!"
Cons: "Todo bien"
Pros: "Service from crew was fine"
Cons: "No delay! Got notification that our flight was one half hour earlier. Then boarded aircraft, and it had electrical problems. Delayed. We had to get off. Then board another aircraft."
Pros: "Time of flight"
Cons: "Aircraft had no screen, old, uncomfortable"
Cons: "Crampt space, cold cabin"
Pros: "None"
Cons: "Long delay"
Pros: "Movie options were good."
Cons: "The a/c was not working well and t"
Pros: "The service was excellent and the flight on time. Love American."
Cons: "The seats have been refurbished and if you are a plus size the seats are uncomfortable."
Pros: "Service"
Cons: "Seats and space"
Cons: "Entertainment via internet could NEVER be really be done complitly. And the flight attendants did not know how to help costumers"
Pros: "Turkey sandwich snd boarding went smoothly"
Cons: "There was no entertainment and since there is no WiFi for most of the flight due to being over water the flight seemed longer than what it actually was."
Pros: "I liked that we got to San Juan safely. The crew on board was very accommodating."
Cons: "Due to the delays, we missed our jumper flight and American refused to compensate. Also, only had two cookies all day from 8:05am until 3:45 pm! No sandwiches as promised. We were delayed approximately 4 hours total. Had to take a taxi ($85) to Fajardo to HOPEFULLY catch last ferry to Culebra. Guess AmericansAirlines doesn’t care if you have to sleep at the dock!"
Cons: "Dallas to San Juan San Juan Dallas American Airlines has the worst seat of any airline flown by us fare almost 2000 dollars for round trip and the seat is small hard uncomfortable even for a short flight this is no business class!!"
Pros: "On time"
Cons: "Cold cabin"
Cons: "The seats are very tight."
Cons: "Last minute cancellation and reschedule if original flight with 20 people hounding the gate for standby status. Craziness. These last minute revisions mist stop"
Pros: "Direct flight"
Cons: "Horrible customer service, excessive baggage fees, rude counter staff, no leg room, narrow seats"
Pros: "USB Outlets are nice to have"
Cons: "Nothing was bad on this flight"
Pros: "Schedule was punctual. The entertainment was superb. Good crew. The overhead bins were, for some reason, larger which aided the boarding process."
Cons: "I guess the lack of snack options but that is just the way it is nowadays."
Pros: "Nice crew clean airplane"
Cons: "Initial flight was cancelled after 2 hours delay. My next flight was scheduled the earliest possible by AA which was 24 hours later. No transportation,hotel or miles compensation for this. I had work and responsabilities the next day. TThe scheduled trip was supposed to take off at 7:45. Boarding started late and was very slow. My bag fit the meassurements and still was forced to check it (which I did not want to do as I did not want to be waiting an hour for my bag at my arrival as I had work early the next day. In addition there was airplaine traffic as it was "rush hour" instead of flying at 7:45 we departed almost at 9pm!!!! Have to pay for food Quality of tv monitors very poor And in an uncomfortable position No movie options No wifi although stated the aircraft has Non functioning electrical plug"
Pros: "Nothing"
Cons: "Never made it to San Juan to catch my cruise. To top things off I was a ship for two days without my luggage and underwears. Never again!!! Thank you JetBlue!!!"
Cons: "That all the passengers were rechecked at the Gate by TSA without offering any explanation as to why, if it was a domestic flight, why were they requiring ID again. And checking bags."
Pros: "On time smooth"
Pros: "The pilot was a riot, the flight was on time. Again, nothing wrong, nothing special. As it should be (if only we had more leg and seat room, and I am pretty streamline)."
Pros: "Nothing"
Cons: "Super old planes, no had a tv."
Pros: "Puntuality"
Pros: "Crew was good."
Cons: "The television was in the aisle and couldn't be properly seen. Also there was no outlet charger. During boarding, even thou they called by group number, the crew allowed a queue in the front, making it confusing who was in line and who wasn't. Better wait till the end to board that get in that mess"
Cons: "There seets are two small. And they dont sell alcohol. That sucks."
Cons: "The airline had trouble with the plane. After we waited 3 hrs in the plane they cancel the flight. They offer a hotel but it was very dirty"
Pros: "Nothing. My fight from San Juan to Miami on Friday Oct. 7 was cancelled because of hurricane Matthews, since I didnot buy a roundtrip with AA they did not reimburse or offer me a credit for my returning flight. I contacted AA in two ocassions and both times their personnel were impersonal and even rude to me with the whole situation. I ended up losing $250 because of choosing American Airlines. I will do my best to avoid traveling with American ever again, and I will spread the word, as well. I felt robbed, so unfair."
Cons: "Everything"
Pros: "Friendly polite staff. Plane left and arrived on time."
Cons: "No have owned screen TV"
Pros: "Everything"
Cons: "Nothing"
Pros: "Comfortable seat"
Cons: "Lack of entertainment"
Cons: "One hour delay sitting inside the plane with no pilot!! And to top it off, the air conditioner was off!! Will never fly American ever again."
Cons: "Terrible airport assistance, many unnecessary customs checks, uncomfortable seats, on flight bad service and late flight times."
Cons: "Gg"
Pros: "Everything was on time, no delays."
Pros: "I live the service which make me feel good. Also the flight was very quiet and the crew help me in everything I asked."

Book cheap flights from Worcester to Caribbean

Recent round-trip flight deals

8/26Fri
1 stopJetBlue
5h 39mORH-SJU
8/27Sat
1 stopJetBlue
7h 40mSJU-ORH
$359
8/27Sat
1 stopJetBlue
5h 39mORH-SJU
8/30Tue
1 stopJetBlue
7h 40mSJU-ORH
$365
8/16Tue
1 stopJetBlue
8h 00mORH-SJU
8/27Sat
1 stopJetBlue
7h 40mSJU-ORH
$385
8/18Thu
1 stopJetBlue
8h 00mORH-SJU
8/22Mon
1 stopJetBlue
7h 40mSJU-ORH
$448
10/10Mon
1 stopJetBlue
9h 47mORH-SJU
10/16Sun
1 stopJetBlue
8h 10mSJU-ORH
$468
9/24Sat
1 stopMultiple Airlines
11h 08mORH-SDQ
10/1Sat
2 stopsMultiple Airlines
18h 01mSDQ-ORH
$475
9/24Sat
1 stopMultiple Airlines
6h 24mORH-SDQ
9/30Fri
1 stopMultiple Airlines
15h 11mSDQ-ORH
$492
8/18Thu
2 stopsMultiple Airlines
31h 36mORH-SJU
8/22Mon
1 stopMultiple Airlines
7h 40mSJU-ORH
$494
9/24Sat
1 stopJetBlue
11h 08mORH-SDQ
10/1Sat
1 stopJetBlue
12h 29mSDQ-ORH
$497
9/24Sat
1 stopMultiple Airlines
6h 24mORH-SDQ
9/30Fri
2 stopsMultiple Airlines
19h 21mSDQ-ORH
$498
7/19Tue
1 stopJetBlue
5h 39mORH-SJU
7/21Thu
1 stopJetBlue
7h 40mSJU-ORH
$499
7/19Tue
1 stopJetBlue
12h 29mORH-BGI
7/22Fri
1 stopJetBlue
9h 34mBGI-ORH
$503
10/10Mon
2 stopsAmerican Airlines
32h 05mORH-SJU
10/16Sun
2 stopsAmerican Airlines
18h 18mSJU-ORH
$530
9/20Tue
2 stopsAmerican Airlines
21h 49mORH-PUJ
9/25Sun
1 stopAmerican Airlines
24h 39mPUJ-ORH
$556
9/24Sat
2 stopsAmerican Airlines
25h 26mORH-SDQ
10/1Sat
2 stopsAmerican Airlines
18h 01mSDQ-ORH
$557
9/20Tue
1 stopAmerican Airlines
21h 23mORH-PUJ
9/25Sun
1 stopAmerican Airlines
24h 39mPUJ-ORH
$557
7/12Tue
2 stopsAmerican Airlines
21h 28mORH-SJU
7/14Thu
2 stopsAmerican Airlines
18h 06mSJU-ORH
$559
7/20Wed
2 stopsMultiple Airlines
21h 28mORH-SJU
7/26Tue
1 stopMultiple Airlines
7h 40mSJU-ORH
$580
7/13Wed
2 stopsAmerican Airlines
33h 07mORH-SJU
7/16Sat
2 stopsAmerican Airlines
21h 05mSJU-ORH
$586
12/1Thu
1 stopMultiple Airlines
20h 37mORH-SDQ
12/3Sat
1 stopMultiple Airlines
19h 52mSDQ-ORH
$592

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Recent one-way flight deals

8/26Fri
1 stopJetBlue
5h 39mORH-SJU
8/27Sat
1 stopJetBlue
7h 40mSJU-ORH
$359
8/27Sat
1 stopJetBlue
5h 39mORH-SJU
8/30Tue
1 stopJetBlue
7h 40mSJU-ORH
$365
8/16Tue
1 stopJetBlue
8h 00mORH-SJU
8/27Sat
1 stopJetBlue
7h 40mSJU-ORH
$385
8/18Thu
1 stopJetBlue
8h 00mORH-SJU
8/22Mon
1 stopJetBlue
7h 40mSJU-ORH
$448
10/10Mon
1 stopJetBlue
9h 47mORH-SJU
10/16Sun
1 stopJetBlue
8h 10mSJU-ORH
$468
9/24Sat
1 stopMultiple Airlines
11h 08mORH-SDQ
10/1Sat
2 stopsMultiple Airlines
18h 01mSDQ-ORH
$475
9/24Sat
1 stopMultiple Airlines
6h 24mORH-SDQ
9/30Fri
1 stopMultiple Airlines
15h 11mSDQ-ORH
$492
8/18Thu
2 stopsMultiple Airlines
31h 36mORH-SJU
8/22Mon
1 stopMultiple Airlines
7h 40mSJU-ORH
$494
9/24Sat
1 stopJetBlue
11h 08mORH-SDQ
10/1Sat
1 stopJetBlue
12h 29mSDQ-ORH
$497
9/24Sat
1 stopMultiple Airlines
6h 24mORH-SDQ
9/30Fri
2 stopsMultiple Airlines
19h 21mSDQ-ORH
$498
7/19Tue
1 stopJetBlue
5h 39mORH-SJU
7/21Thu
1 stopJetBlue
7h 40mSJU-ORH
$499
7/19Tue
1 stopJetBlue
12h 29mORH-BGI
7/22Fri
1 stopJetBlue
9h 34mBGI-ORH
$503
10/10Mon
2 stopsAmerican Airlines
32h 05mORH-SJU
10/16Sun
2 stopsAmerican Airlines
18h 18mSJU-ORH
$530
9/20Tue
2 stopsAmerican Airlines
21h 49mORH-PUJ
9/25Sun
1 stopAmerican Airlines
24h 39mPUJ-ORH
$556
9/24Sat
2 stopsAmerican Airlines
25h 26mORH-SDQ
10/1Sat
2 stopsAmerican Airlines
18h 01mSDQ-ORH
$557
9/20Tue
1 stopAmerican Airlines
21h 23mORH-PUJ
9/25Sun
1 stopAmerican Airlines
24h 39mPUJ-ORH
$557
7/12Tue
2 stopsAmerican Airlines
21h 28mORH-SJU
7/14Thu
2 stopsAmerican Airlines
18h 06mSJU-ORH
$559
7/20Wed
2 stopsMultiple Airlines
21h 28mORH-SJU
7/26Tue
1 stopMultiple Airlines
7h 40mSJU-ORH
$580
7/13Wed
2 stopsAmerican Airlines
33h 07mORH-SJU
7/16Sat
2 stopsAmerican Airlines
21h 05mSJU-ORH
$586
12/1Thu
1 stopMultiple Airlines
20h 37mORH-SDQ
12/3Sat
1 stopMultiple Airlines
19h 52mSDQ-ORH
$592

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Worcester - Caribbean Flights