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Find cheap flights from Hartford to Caribbean from $72

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Hartford to Caribbean departing on 6/6. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
0 bags
Sat 6/29
Sat 7/6

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Best Caribbean Flight Deals

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours

Punta Cana
Punta Cana2 stops$262
Montego Bay
Montego Bay1 stop$315
Santo Domingo
Santo Domingo1 stop$243
Oranjestad
Oranjestad1 stop$443
Nassau
Nassau1 stop$288
Kingston
Kingston1 stop$442
Simpson Bay
Simpson Bay1 stop$310
Providenciales
Providenciales1 stop$413
Port of Spain
Port of Spain2 stops$705
Bridgetown
Bridgetown1 stop$584
George Town
George Town2 stops$444
Aguadilla
Aguadilla1 stop$277
Willemstad
Willemstad1 stop$499
St. John's
St. John's1 stop$595

Good to know

Low season

September

High season

February

Cheapest flight

$72
Best time to beat the crowds with an average 20% drop in price.
Most popular time to fly and prices are also 9% lower on average.
Flight from Hartford to San Juan Airport

FAQs - booking Caribbean flights

  • Which kid-friendly airline should I consider for my flight from Hartford to the Caribbean with my kids?

    JetBlue is one of the kid-friendly airlines that travelers can choose for their flights from Hartford to the Caribbean with their children. The airline provides various kid-friendly amenities, ensuring that parents and their children have a wonderful trip. Priority boarding for families with children, toys, activities, and special meals for children are among these amenities.

  • Which eco-friendly airline should I fly with from Hartford to the Caribbean?

    Delta is one of the environmentally friendly airlines to choose for your travel from Hartford to the Caribbean. The airline promotes environmentally friendly programs such as sustainable fuel usage, improved aircraft technology, and waste reduction. These projects attempt to reduce carbon emissions, promote environmental conservation, and help to make the aviation sector more sustainable.

  • How convenient are the flights from Hartford to the Caribbean for Persons with Reduced Mobility (PRMs)?

    Traveling from Hartford to the Caribbean should be smooth for Persons with Reduced Mobility (PRMs) because most airlines, including United and Spirit Airlines, prioritize PRMs. In addition to providing priority boarding for PRMs, which allows them to settle in early by selecting their desired and suitable seats, these airlines provide complimentary wheelchair services at both departure and destination airports. They also have qualified specialists whose main aim is to provide PRMs with specialized services.

  • Which pet-friendly airline should I consider from Hartford to the Caribbean?

    One of the pet-friendly airlines you should consider for your flight from Hartford to the Caribbean with your pet is American Airlines. The airline's pet-friendly policy allows you to travel with smaller pets in the cabin, provided their carrier can fit the seats. Larger pets can be transported in the pressure and temperature-controlled cargo hold.

  • How does KAYAK find such low prices on flights from Hartford to Caribbean?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Hartford to Caribbean.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Hartford to Caribbean?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Caribbean from Hartford is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Hartford to Caribbean?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Caribbean with an airline and back to Hartford with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Hartford to Caribbean?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Caribbean from Hartford up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

See more FAQs

Top tips for finding cheap flights to Caribbean

  • Looking for a cheap flight? 25% of our users found tickets from Hartford to the following destinations at these prices or less: San Juan $99 one-way - $198 round-trip
  • Morning departure is around 23% cheaper than an evening flight, on average*.
  • Most passengers flying from Hartford to the Caribbean depart through Bradley International Airport (BDL). You may need to use a cab, a ridesharing service like Lyft or Uber, or the CTfastrak Bradley Flyer bus service to connect from the city center to Bradley Intl for your trip to the Caribbean.
  • Frontier or Copa Airlines are your best airline options when traveling from Hartford to the Caribbean with a significant amount of luggage. Aside from exempting a handbag and a computer from usual luggage fees, the airlines' lenient carry-on policy exempts basic goods such as strollers, child seats, and medical equipment from their standard rates.
  • When traveling from Hartford to the Caribbean on a fixed timetable, you should consider flying with either Spirit or Frontier Airlines. These two are among the few that offer limited direct flights from Bradley International Airport (BDL) to the Caribbean through San Juan Airport (SJU). Because of the direct flights, they are among the quickest alternatives on this trip.
  • Book your trip from Hartford to the Caribbean with American or JetBlue Airways to take advantage of class and ticket upgrade opportunities. These airlines may send you an email urging you to upgrade from Economy to Business or First Class at a discounted charge, especially during your first stopover.
  • Because most airlines flying from Hartford to the Caribbean have at least one stopover, you should factor in your layovers while planning and budgeting for your trip. Airlines departing from Bradley International (BDL) frequently stop at Orlando (MCO), Fort Lauderdale (FLL), and Raleigh-Durham (RDU).
See more tips
*Average of the lowest prices shown in KAYAK’s search results for departures within the next 30 days

Top 5 airlines serving from Hartford to Caribbean

 
Need help choosing which airline to fly with from Hartford to Caribbean? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
8.0
DeltaOverall score based on 10457 reviews
8.6Crew
7.9Comfort
7.4Food
8.0Entertainment
8.2Boarding
Airline reviews

I've flown many many times on Northwest and then Delta. The crew on this flight were absolutely the best I've had the pleasure of being looked after by.

10.0 ExcellentAnonymous, May 2024MSP - YVR
Read more about Delta reviews

I've flown many many times on Northwest and then Delta. The crew on this flight were absolutely the best I've had the pleasure of being looked after by.

Flew first class so everything was great. But maybe because the flights were red eye, no meals were served, just chips. I flew Alaska Air 1st class at 9PM (2 hour flight) and they served beef short rib sliders!

Had to change aircraft due to a faulty door. Surprisingly it only caused about an hour and a half of delay. Delta handled this situation as well as can be expected.

Awful. Flight was continuously getting delayed and gates kept changing without any reason. Flight was delayed for more then 3 hours

Paid premium for Delta only to be on safe but tired old 767 with ancient cabin in mediocre condition. Poor wifi and horrible inflight entertainment. Hardly a premium experience. Should have flown SW and had fun flight crew and no pretense

Our flight to Zurich was delayed by almost 3 hours, so we missed our next flight. There was no indication it would be delayed this much. We were told the gate had changed and then it apparently took over 2 hours to load the "catering" on the plane. We were not compensated in any way for the trouble.

Rated entertainment as Mediocre as there were major problems with the Infotainment system that took probably a half hour for them to fix.

Your crew could maybe answer the call bell at least one of the times I pressed it. I pressed it first time with 2.5 hours left in our flight bc my partner was hungry and wanted a sandwich. We finally got the sandwich with 40 mins left in the flight.

Half the bathrooms assigned to economy were out of action

Delta crushed it. Flight attendant in first was attentive and just never stopped. Honestly one of the best domestic flights I’ve been on.

Overall fine but both ways for this trip was delayed.

Flight was delayed by almost 5 hours. Suitcase was not loaded despite the flight being near empty (my colleagues’ suitcases did reach JFK, unlike mine). Had to argue on phone to get JetBlue to deliver the case to my hotel. Never again

The flight was excellent. The crew was welcoming and attentive.

Great! I love Jet Blue. My favorite airline! Very efficient, clean and timely.

Run out of snack choices. Why are the seats not padded for your butt? Are we sitting on blocks of wood or metal for $250-300 a pop? This ain’t spirit. Let’s get it together people

We were told that our flight would be delayed for 90+ minutes because of weather, so we went to get something to eat only to have them randomly start boarding 15 minutes after the announcement, with no warning.

Entertainment... No earphones passed out. Many including me couldn't use the TV. Legroom was good. Crew was indifferent and a bit surly. Free wifi was a nice convenience. Check in desk location was unknown. Gate number on the boarding passes was wrong.

Going through JFK’s security is a mess. The TSA security said no shoes on the bins. So, we place our shoes in the belt and they came out all over the belt. Boarding was delayed and Flight as well.

Safe and on time were the positives. The plane wasn't cleaned before boarding, there was garbage and food on the floor and in the seat pocket. The TV screen was small and the picture fuzzy, audio quality was poor. Seatbelt was fraying and seat did not recline properly. No charging ports near the seats,

Confusing. Delay updates were out of whack At one point it said my flight was 25 hours. Three gate changes and two delays only to change back to original departure time. Gate announcer and on board flight attendant (Alejandro) making the announcements was impossible to understand due to accent and speed of speech. After beverage service the rear flight attendants sat back there on their phones. No refills no checking in, one sweep through for trash collection. Very impersonal. Bring back Coke products

very very tight seats unfriendly crew who do not seem to care about the comfort of their passengers and do not know how to smile poor ground staff support at LHR and PHX

The boarding process and flight were great. However, I waited about 40 minutes for my luggage. It did not come up on the designated belt. Instead, everyone’s bags were on a cart. Not sure what the issue was, but we were not informed until another passenger went looking for her bags and found them.

There were delays on both ends. It made it less than excellent. This plane was great though

AA1537 the AC was not working properly. It was very hot and uncomfortable.

So uncomfortable to sit in the tiny space on a long, international. Food was rough. Please, less white flour and processed food.

Worst experience flying American Airlines. I fly with them often, so I was super disappointed in the service I received at gate 30 in LGA on May 24, mid-day. The flight was delayed twice. I was patiently waiting in the American Airlines lounge when I received the notice on my app that the plane was boarding 45 minutes before its newly re-scheduled take off of 4 pm (from the orginal 1:45 pm then 3:00 pm). It took me 5 min to travel from the lounge to the gate and when I arrived there at 3:20 flight gate attendant told me the flight had closed and that they announced for passengers multiple times. I showed them the notification on my app and they were really rude and unempathetic. The person who rescheduled my flight at customer service wasn't any happier but was at least helpful in getting me on the next flight.

Flight was 1/2 hour delayed leaving Phoenix. Otherwise it was an average flight. Flight crew on this trip was very nice.

Our flight was delayed 2.5 hrs due to plane being too hot! After 1.5 hrs, airline decided to use another plane but had to wait for gate, baggage transfer & beverage transfer. Anyone could tell after first half hour that another plane was required and although did not affect us many would miss connecting flights at Heathrow. I have found the stewards are not the friendliest in the industry and the food is questionable, even as I like airplane food normally, the best of the 2 flights was the yogurt & granola for breakfast.

Everything was great except for the wifi was junk. Crew was super friendly and helpful

Was lucky to have a employee at the AA checkin counter that had compassion and understood they ordeal that we went through with our original flight being diverted, needing to stay in the aircraft and then flying to the original destination; adding hours to the trip and forcing us to miss our connection and our rebooked connection. She was able to get up on standby on the highest priority on the next flight to the closest airport we need to be at and it all worked out despite being many hours late.

EVERYTHING WAS WONDERFUL HOSPITALITY THE HELP.THE SEATING FRIENDLY ALWAYS HAVE A GOOD RIDE NOT ONE BAD EXPERIENCE WITH THEM

This was the smoothest flight I have had in awhile. I was also offered an exit row seat for a great upgrade cost and was able to sleep almost thr whole flight due to comfort and a smooth flight. We left on time and arrived on time.

No food not even water offered unless you buy it and no usb in the seat but other than that everything was good

Because our flight from marsh Harbor to Fort Lauderdale was over three hours delayed it caused us to miss our flight in Fort Lauderdale. Because we missed that flight, it cost us nearly $100 apiece for four different travelers which totaled nearly $400. We are seeking a reimbursement for the flight that we missed in Fort Lauderdale Florida.

Flight expected to leave at 6:40 pm ended leaving at 8:00 am the following day. I slept in a cold airport. Never again Spirit for me…

Flight was cancelled just 6 days before. No more flights that day, and the following date was sold out. Had to obtain a refund and buy more expensive flights on another airline.

The flight was on time and nice as always for me with spirit but the cabin crew were not good. They left the lights on on a red eye for the entire flight.

This was the return leg of my journey with Spirit Airlines. Despite its reputation, I found no issues as it got me from point A to B safely and without delay, especially with no mechanical delays, which is fantastic in my book! The staff, from ground crew to cabin crew, were all pleasant and hassle-free. The flight was smooth from takeoff to landing. I have absolutely no complaints about this no-frills airline!

I got a one-way, last-minute nonstop flight from PDX to BWI for only $125. Yes, I got nicked $79 more for a checked suitcase and $89 more for the BIG SEAT option, but it was worth it, even with $4.50 for coffee and $10 for a snack (the latter no different than any other airline). The grand total was still less flying on any other airline.

It was the worst ever, i will be filing a lawsuit to get a refund. Our flight was delayed 4 hours so we would miss our connecting flight, we were not rebooked to our destination the same day, we were not offered any options to get home on the same day despite being clear that we absolutely cannot get stranded at night due to family, we were forced to book our own flights on a different airline to get home, and spririt is refusing a refund because our flight wasn't cancelled, only delayed. oh yeah, and they lost our luggage on the first part of the trip and you cannot get a hold of customer service when anything goes wrong, on hold for 30+ minutes. and their app breaks so you can't use that either.

9hrs delay and didn’t provided anything until after flight landed $75 voucher for fiuture travel no meals or anything.

It was ridiculously hard to check in for the flight, and Frontier charged us a LOT of money to have a carry on suitcase, and then told everyone we could not carry on bags and had to check them through at the gate, and didn't refund the extra money we paid to have the suitcase as carry on.

I had a terrible experience with Frontier. I arrived before the 60 minute cut off and was told that Frontier has a two hour window for bags. I was then told the next available flight wasn’t until the end of the day (I had booked a 6am flight). I took a look around and saw other people being told that they could not board their flights or that they had to pay additional fees. I opted to rebook on American Airlines. There’s absolutely no straightforward way to contact Frontier, so this ticket was a complete waste of money. Oh - and the kicker is that the lady lied about the two hour cut off.

Frontier won’t help you at the airport without paying $25. Carry on was $75. Then you get on the plain and every beverage or snack is also a charge. Seats are hard and real packed in. I would never fly them again.

Worst experience I have seen. The flight was cancelled without any reason.

My experience with frontier staff at the Denver airport was absolutely horrible. The manager on duty was even worst if was the worst experience I have ever had, I have never been treated so poorly as a customer in my life! The staff was extremely rude, eye rolls and attitude and then refusal to help me at all. I wish I could never fly frontier again that’s how horrible it was!

The Frontier app wasn’t working. So I could not pay for a carry on the week prior to flying. They charged me 99$ at the gate to carry on a duffle bag.

Good for the price. My only complaint is that the pilot should keep the air flowing while passengers are waiting to getting out of airplane.

Plane could have been more on time. More leg room .

I arrived 1 hour prior to boarding, and they said I was too late for a domestic flight. First time I heard that :-(

Book cheap flights from Hartford to Caribbean

Recent round-trip flight deals

6/10Mon
nonstopFrontier
3h 47mBDL-SJU
6/19Wed
nonstopFrontier
3h 47mSJU-BDL
$161
6/11Tue
nonstopFrontier
3h 47mBDL-SJU
6/17Mon
nonstopFrontier
3h 47mSJU-BDL
$171
9/4Wed
2 stopsSpirit Airlines
19h 21mBDL-SJU
9/10Tue
2 stopsSpirit Airlines
13h 27mSJU-BDL
$181
9/19Thu
1 stopSpirit Airlines
17h 07mBDL-SJU
9/24Tue
1 stopSpirit Airlines
7h 35mSJU-BDL
$183
11/5Tue
nonstopJetBlue
3h 48mBDL-SJU
11/13Wed
nonstopJetBlue
4h 08mSJU-BDL
$219
6/10Mon
nonstopJetBlue
3h 52mBDL-SJU
6/18Tue
nonstopJetBlue
3h 58mSJU-BDL
$259
8/14Wed
1 stopAmerican Airlines
6h 04mBDL-NAS
8/21Wed
1 stopAmerican Airlines
8h 29mNAS-BDL
$288
9/14Sat
1 stopDelta
6h 07mBDL-NAS
9/19Thu
1 stopDelta
8h 38mNAS-BDL
$289
8/14Wed
2 stopsAmerican Airlines
10h 52mBDL-NAS
8/21Wed
1 stopAmerican Airlines
6h 04mNAS-BDL
$291
10/15Tue
1 stopDelta
8h 04mBDL-SJU
10/22Tue
1 stopDelta
11h 54mSJU-BDL
$324

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Recent one-way flight deals

6/6Thu
nonstopFrontier
3h 47mBDL-SJU
$72
6/5Wed
2 stopsSpirit Airlines
12h 12mBDL-SJU
$81
7/12Fri
1 stopDelta
9h 43mBDL-NAS
$91
10/2Wed
1 stopAmerican Airlines
10h 34mBDL-SJU
$114
6/5Wed
1 stopAmerican Airlines
9h 09mBDL-SJU
$137
11/7Thu
nonstopJetBlue
3h 48mBDL-SJU
$142
7/29Mon
1 stopDelta
8h 27mBDL-SJU
$162
8/25Sun
1 stopJetBlue
6h 44mBDL-BQN
$173
8/24Sat
2 stopsUnited Airlines
11h 37mBDL-BQN
$242
8/25Sun
2 stopsUnited Airlines
12h 44mBDL-BQN
$312

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Last minute flights from Hartford to Caribbean

Last minute flight, train and bus deals

5/31Fri
nonstopFrontier
3h 47mBDL-SJU
6/4Tue
nonstopFrontier
3h 48mSJU-BDL
$143
5/31Fri
nonstopFrontier
3h 47mBDL-SJU
6/4Tue
nonstopFrontier
3h 48mSJU-BDL
$153
6/4Tue
nonstopJetBlue
4h 04mBDL-SJU
6/4Tue
nonstopJetBlue
4h 03mSJU-BDL
$323
6/3Mon
multi-stopDelta
8h 19mBDL-SJU
6/6Thu
multi-stopDelta
8h 57mSJU-BDL
$329
6/4Tue
nonstopJetBlue
4h 04mBDL-SJU
6/14Fri
nonstopJetBlue
3h 58mSJU-BDL
$349
6/1Sat
multi-stopDelta
8h 19mBDL-SJU
6/5Wed
multi-stopDelta
10h 30mSJU-BDL
$366
5/31Fri
multi-stopAmerican Airlines
10h 25mBDL-SJU
6/5Wed
multi-stopAmerican Airlines
7h 13mSJU-BDL
$388
6/4Tue
multi-stopSpirit Airlines
34h 59mBDL-SJU
6/6Thu
multi-stopSpirit Airlines
33h 35mSJU-BDL
$400
6/4Tue
multi-stopSpirit Airlines
35h 00mBDL-SJU
6/11Tue
multi-stopSpirit Airlines
31h 06mSJU-BDL
$402
5/31Fri
multi-stopAmerican Airlines
10h 25mBDL-SJU
6/5Wed
multi-stopAmerican Airlines
10h 13mSJU-BDL
$438

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