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$37 Find cheap flights from Hartford to Caribbean

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 7/1. 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 7/13
Sat 7/20

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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 Cana1 stop$259
Montego Bay
Montego Bay1 stop$298
Santo Domingo
Santo Domingo1 stop$220
Oranjestad
Oranjestad1 stop$307
Nassau
Nassau1 stop$289
Kingston
Kingston2 stops$421
Simpson Bay
Simpson Bay1 stop$376
Providenciales
Providenciales1 stop$358
Port of Spain
Port of Spain2 stops$677
Bridgetown
Bridgetown2 stops$366
George Town
George Town1 stop$442
Aguadilla
Aguadilla1 stop$248
Willemstad
Willemstad1 stop$552
St. John's
St. John's1 stop$620

Good to know

Low season

September

High season

February

Cheapest flight

$37
Best time to beat the crowds with an average 19% 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 $102 one-way - $208 round-trip
  • Morning departure is around 12% 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 10000 reviews
7.9Comfort
8.2Boarding
8.6Crew
8.0Entertainment
7.4Food
Airline reviews

It was very cold because the air conditioner was on high power, and my son got sick.

4.0 OkayAnonymous, Jun 2024ORD - SEA
Read more about Delta reviews

It was very cold because the air conditioner was on high power, and my son got sick.

3 hours late and all they have is was a $12 meal voucher. That’s not even enough to cover fast food.

Among the poorest flights I’ve had with Delta in a while. Entertainment system failed completely on a 7.5 hr flight. Crew seemed distracted and not the normal friendly crew. Flight overbooked it seemed… very crowded.

If I can, I always fly Delta. I’ve found their service to always be reliable and pleasant.

You could have not cancelled the flight (AA, which I will be flying from now on) left for BOS despite the fictitious weather issues (that no one in my Boston family could see). You could have rebooked my direct flight to another direct flight instead of sending me though JFK, the worst US airport after O’Hara You could have rebooked me on a Main Cabin seat (like the one I paid for in my original ticket instead of putting me a the last row on JFK->BOS leg, pocketing the difference in ticket price But I do not really care whether you will ever do that in a future because in a future neither I nor anyone from my company (unless they pay out of pocket) nor an of my clients and partners (if they heed my advice) will ever be caught dead on any of Delta flights

Really bad baggage handling. Had my Rimowa bag badly damaged at the latches.

It was pretty good I was worried with the short Layover that I might not catch my connection but the gate was there

It was good until there was a 3 hour delay because there was not any pilots to fly the plane.

There was plenty of overhead room but half of the passengers were told they had to check their carryon bags. My partner and I checked in as early as possible and our seats were split across the aisle.

Friendly flight attendants. Comfort plus seats were very comfortable and had lots of leg room. 10A and 10 B.

terrible. Because I felt very unwell during the flight. How do they leave a woman alone in the middle of 2 men? an obese man who was falling on top of me.

They put me on a chair in between two men, one overweight who was almost falling on top of me, and the other was even uncomfortable because I was half falling because of what the other was pushing me. I stayed with. my feet were swollen from fluid retention and from being unable to accommodate myself. it was very uncomfortable. I asked for help but they told me that the flight was full and they couldn't help me. I got off the plane almost unable to walk due to the inflammation. and then at FLL airport I asked for help because I couldn't go to my next flight, which was a connection.

The walk from baggage claim to the taxi is very difficult for older people I will never fly into JFK again. It is physically challenging

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.

Crew never smiled, never helped , told me to make my own bed ( in Upper class), never offered a drink

For the money that I paid it was a good deal. I sat in the back of the plane and didn't pick a seat and my wife I sat together. Mission accomplished.

Seats are weirdly bent, I felt hunched the entire time.

Nothing exceptional. No drink of any type, even in first class was provided for the hour and half trip.

Paid for premium economy had no tv the whole time the crew tried to reset/reboot but would not work they said they would put a trouble ticket in for it. We had 3 seats my tv was the only one that didn't work. They cancelled our flight re worked us on another that left us at airport over night on the floor I have a ten year old and a 78 diabetic mother which also had shingles and suffers from nerve pain in legs and back. Requested wheelchair service at all airports after the re route NO wheelchair service was there to help. WORST experience we have ever had. Went to American airlines assistance it was closed. I AM FURIOUS!!! I expect some sort of compensation from this traumatic experience and no need for flying points we don't plan on using American airlines again!!!!

This is by far the worst experience I have had with American Airlines. The start of this trip was a complete disaster. I purposely planned my trip so that I would weather any delays so that I could make very important meeting at the Pentagon. My flight was cancelled because of maintenance and I was put on the first flight the next day but I was late to the meeting. After a long week at the Pentagon I just wanted to go home and my flight home which was early in the day was delayed. Eventually the flight was delayed until the next day. I was not authorized a hotel room because DCA was my point of origin. So I paid for a hotel out of pocket. The flight this morning was boarded then deplaned because the aircraft was hot. The flow of information was not happening in DCA and made it worse when the news was bad. I am going to take a break from American for my next few military flights. Hopefully whatever has been going on with American Airlines will be resolved.

We had a 2 hour delay. The seats were smaller than most other airlines. The person in front of us wanted to lay back and we had to stop her because she was pressing against my girlfriend’s legs. We had to ask her to sit up and not lay back due to the lack of room.

Information when booking said the flight would be with American Airlines but the flight was actualy with British Airways. Check in from Orlando was nice and quick. I agreed to put my cabin case in the checked luggage as it was a full flight. Case came back damaged (unable to put the handle down) so will have to dispose of it. Seats were quite cramped with very little leg room, even for economy. This was the experience of both the outgoing and return flight. Cabin crew were ok and flight time was punctual.

Everything was fine once we actually got on our flight. It was more then annoying they canceled (delayed) our flight. We lost out on a day of our trip along with money on our stay. Plus we had to book another hotel. So expensive.

This flight was canceled and delayed several times without explanation. The plane was freezing cold and no wifi for messaging. Getting off the plane was terribly unorganized and felt like it took forever….

Poor response to delay, getting on plane, off plane and back on again

My flight was uncomfortable and crammed. There were no pockets to store things, I couldn’t move my seat back slightly. Beverages including soda cost extra. My husband flew on another spirit airline flight, which was delayed a total of 48 hours, only to be canceled.

Two delays in less than 24hrs. They need to improve everything and restructure the whole company.

Terrible leg room, seats don’t recline, delayed flight, and even water isn’t free onboard

Flight was canceled less than 6 hours before takeoff, rebooked on a flight that was twice as long and left earlier so we couldn’t make it, when using text support option took over 2 hours to speak with someone.

Not enough help at airport during boarding process. Flight was delayed. Overall WORST flying experience I’ve ever had. Will NEVER FLT SPIRIT AGAIN

Terrible legroom, seats do not recline, tray table the size of an iPhone, delayed flight, have to pay 5$ to get a cup of water onboard.

Could have TV/Movie and some water ou soda free

Flight was good and clean but delayed over an hour on the return flight.

The non stop flight and able to go into Atlantic City airport. They could lower the prices. It starts out low but then if you want to bring luggage and pick your seat the price goes up quite a bit.

Online check-in was not user-friendly. Too many fees, not cost effective.

They wouldn’t let us on the flight even tho we were an hour early. No refund not even our bags that were prepaid

I brought a ticket and car rental through Travelocity. There was no where to add a KTN. So I thought i’d add it by looking up ticket on frontier website. I tried 3 times with the frontier chat bot to add my KTN it never updated my boarding pass. So then I tried showing up early to do it in person at the airport. The first employee update my ktn in the system and gave me a new boarding pass. I was sent back by tsa to join regular line. Then I was told to add my Ktn. It would cost me $25 extra. Given the length of the cue I did pay. Congratulations! BUT I will NEVER fly frontier again. Plus the plane was very old. It had actual ashtrays and old looking tray backs. Worst travel experience ever. Im warning my friends and family not to use frontier ever.

I did not enjoy the trip home on Frontier for several reasons: there is too much cost besides the flight, which was more than I would normally pay, then having to pay for luggage, and carry-on, seat (if you want to reserve when booking) then you must pay over $3 for a can of soda, and $4 for a snack. A cup of water is free.

Did not realize seats did not recline. Best to travel in an exit row... No question

I strongly dislike Frontier. I find them barebones, the seats not particularly comfortable, the nickel and diming is maddening, the app is TERRIBLE - super confusing to navigate, and the last 4 frontier flights I have flown have been on AVERAGE 2 hours late, one ruining a fancy night out in Vegas with reservations made well in advance, which was nodded to with a measly 5000 miles, which translates to almost nothing. At least credit a free checked bag or something.

8 hr delay. had to buy another ticket with another airline

Four and a half hour delay in total. What frustrates me most is the poor communication and disorganization.

I appreciated the upgrade to free cary-on bag and seat selection at no charge

FRONTIER SUCKS! The agent downstairs tricked me into booking, just to get to the gate. At the gate, they told me they couldn't help. I then called Customer Service. They and the gate attendants kept blaming each other. Neither side was willing to help the customer.

Book cheap flights from Hartford to Caribbean

Recent round-trip flight deals

7/1Mon
nonstopFrontier
3h 47mBDL-SJU
7/13Sat
nonstopFrontier
3h 58mSJU-BDL
$122
7/1Mon
nonstopFrontier
3h 47mBDL-SJU
7/13Sat
nonstopFrontier
3h 58mSJU-BDL
$138
9/7Sat
1 stopSpirit Airlines
11h 54mBDL-SJU
9/9Mon
2 stopsSpirit Airlines
27h 45mSJU-BDL
$181
8/14Wed
1 stopSpirit Airlines
11h 46mBDL-SJU
8/21Wed
1 stopSpirit Airlines
8h 42mSJU-BDL
$182
10/26Sat
2 stopsAmerican Airlines
17h 12mBDL-SJU
11/2Sat
2 stopsAmerican Airlines
24h 33mSJU-BDL
$268
8/27Tue
1 stopJetBlue
10h 18mBDL-SJU
9/2Mon
nonstopJetBlue
3h 58mSJU-BDL
$281
7/10Wed
1 stopAmerican Airlines
14h 27mBDL-NAS
7/17Wed
1 stopAmerican Airlines
14h 24mNAS-BDL
$289
9/14Sat
1 stopDelta
7h 11mBDL-NAS
9/18Wed
1 stopDelta
10h 28mNAS-BDL
$299
8/8Thu
1 stopDelta
16h 46mBDL-NAS
8/15Thu
1 stopDelta
8h 42mNAS-BDL
$304
8/23Fri
nonstopJetBlue
4h 00mBDL-SJU
9/1Sun
nonstopJetBlue
3h 58mSJU-BDL
$309

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Recent one-way flight deals

7/1Mon
nonstopFrontier
3h 47mBDL-SJU
$37
7/1Mon
nonstopFrontier
3h 47mBDL-SJU
$39
11/9Sat
1 stopSpirit Airlines
10h 54mBDL-SJU
$84
10/9Wed
1 stopSpirit Airlines
10h 54mBDL-SJU
$90
8/2Fri
1 stopAmerican Airlines
14h 27mBDL-NAS
$91
8/2Fri
2 stopsAmerican Airlines
14h 57mBDL-NAS
$117
6/28Fri
1 stopDelta
8h 26mBDL-SJU
$162
7/10Wed
nonstopJetBlue
3h 56mBDL-SJU
$179
6/28Fri
1 stopDelta
8h 26mBDL-SJU
$183
7/31Wed
1 stopJetBlue
11h 40mBDL-PUJ
$206

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Last minute flights from Hartford to Caribbean

Last minute flight, train and bus deals

6/16Sun
nonstopFrontier
3h 47mBDL-SJU
6/20Thu
nonstopFrontier
3h 47mSJU-BDL
$215
6/18Tue
multi-stopFrontier
7h 55mBDL-SJU
6/24Mon
nonstopFrontier
3h 47mSJU-BDL
$218
6/16Sun
nonstopFrontier
3h 47mBDL-SJU
6/18Tue
nonstopFrontier
3h 47mSJU-BDL
$227
6/18Tue
nonstopFrontier
3h 47mBDL-SJU
6/24Mon
nonstopFrontier
3h 47mSJU-BDL
$228
6/15Sat
nonstopJetBlue
3h 56mBDL-SJU
6/20Thu
nonstopJetBlue
3h 58mSJU-BDL
$329
6/15Sat
nonstopJetBlue
3h 56mBDL-SJU
6/26Wed
nonstopJetBlue
3h 58mSJU-BDL
$378
6/16Sun
multi-stopAmerican Airlines
11h 35mBDL-SJU
6/20Thu
multi-stopAmerican Airlines
16h 26mSJU-BDL
$388
6/16Sun
multi-stopAmerican Airlines
13h 20mBDL-SJU
6/17Mon
multi-stopAmerican Airlines
16h 20mSJU-BDL
$403
6/18Tue
multi-stopSpirit Airlines
20h 16mBDL-KIN
6/29Sat
multi-stopSpirit Airlines
21h 12mKIN-BDL
$724
6/14Fri
multi-stopDelta
18h 41mBDL-SXM
6/19Wed
multi-stopDelta
8h 36mSXM-BDL
$1,167

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