$118 Find Cheap Flights from Hartford to Caribbean - Compare and Save

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 8/7. 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.
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Cheap Flights from Hartford to Caribbean

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Punta Cana
Punta Cana2 stops$372
Santo Domingo
Santo Domingo1 stop$398
Montego Bay
Montego Bay2 stops$407
Oranjestad
Oranjestad1 stop$451
Nassau
Nassau1 stop$408
Kingston
Kingston1 stop$456
Simpson Bay
Simpson Bay1 stop$424
Providenciales
Providenciales1 stop$553
Port of Spain
Port of Spain1 stop$348
Bridgetown
Bridgetown1 stop$400
George Town
George Town1 stop$357
Willemstad
Willemstad1 stop$413
Aguadilla
Aguadilla1 stop$322
St. John's
St. John's1 stop$630
Puerto Plata
Puerto Plata1 stop$581
Punta Cana
Punta Cana2 stops$372
Santo Domingo
Santo Domingo1 stop$398
Montego Bay
Montego Bay2 stops$407
Oranjestad
Oranjestad1 stop$451
Nassau
Nassau1 stop$408
Kingston
Kingston1 stop$456
Simpson Bay
Simpson Bay1 stop$424
Providenciales
Providenciales1 stop$553
Port of Spain
Port of Spain1 stop$348
Bridgetown
Bridgetown1 stop$400
George Town
George Town1 stop$357
Willemstad
Willemstad1 stop$413
Aguadilla
Aguadilla1 stop$322
St. John's
St. John's1 stop$630
Puerto Plata
Puerto Plata1 stop$581

Book Cheap Hartford to Caribbean Plane Tickets

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Hartford to Caribbean that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Hartford to Caribbean

Thu, Aug 27 - Sun, Aug 30
Frontier Logo
1:42 pm - 5:46 pm
BDL
-
SJU
4h 04mnonstop
Frontier Logo
8:45 am - 12:47 pm
SJU
-
BDL
4h 02mnonstop
$258Frontier
Thu, Aug 27 - Mon, Aug 31
Frontier Logo
1:42 pm - 5:46 pm
BDL
-
SJU
4h 04mnonstop
Frontier Logo
8:45 am - 12:47 pm
SJU
-
BDL
4h 02mnonstop
$258Frontier
Fri, Sep 4 - Wed, Sep 9
Multiple Airlines Logo
1:42 pm - 5:46 pm
BDL
-
SJU
4h 04mnonstop
Multiple Airlines Logo
6:42 pm - 11:36 pm
SJU
-
BDL
28h 54m
2 stops
$258Multiple Airlines
Thu, Sep 3 - Wed, Sep 9
Multiple Airlines Logo
1:42 pm - 5:46 pm
BDL
-
SJU
4h 04mnonstop
Multiple Airlines Logo
6:42 pm - 11:36 pm
SJU
-
BDL
28h 54m
2 stops
$258Multiple Airlines
Fri, Aug 28 - Fri, Sep 4
Southwest Logo
3:40 pm - 10:50 pm
BDL
-
SJU
7h 10m
1 stop
Southwest Logo
3:20 pm - 10:15 pm
SJU
-
BDL
6h 55m
1 stop
$259Southwest
Wed, Sep 2 - Wed, Sep 9
Southwest Logo
3:05 pm - 10:00 pm
BDL
-
SJU
6h 55m
1 stop
Southwest Logo
2:25 pm - 9:15 pm
SJU
-
BDL
6h 50m
1 stop
$259Southwest
Tue, Sep 22 - Thu, Oct 1
Delta Logo
2:05 pm - 10:19 pm
BDL
-
SJU
8h 14m
1 stop
Delta Logo
2:59 pm - 11:59 pm
SJU
-
BDL
9h 00m
1 stop
$264Delta
Sat, Sep 12 - Sat, Sep 19
Delta Logo
5:30 am - 1:16 pm
BDL
-
SJU
7h 46m
1 stop
Delta Logo
2:30 pm - 11:12 pm
SJU
-
BDL
8h 42m
1 stop
$264Delta
Sat, Sep 12 - Sat, Sep 19
JetBlue Logo
2:06 pm - 6:04 pm
BDL
-
SJU
3h 58mnonstop
JetBlue Logo
8:25 am - 12:22 pm
SJU
-
BDL
3h 57mnonstop
$283JetBlue
Thu, Sep 24 - Sun, Sep 27
JetBlue Logo
2:06 pm - 6:04 pm
BDL
-
SJU
3h 58mnonstop
JetBlue Logo
8:30 am - 12:27 pm
SJU
-
BDL
3h 57mnonstop
$283JetBlue
Booking Insights

KAYAK's insights & trends for Hartford to Caribbean flights

Get data-powered insights and trends into flights from Hartford to Caribbean to help you find the cheapest flights, the best time to fly and much more.

What is the cheapest Hartford to Caribbean flight route?

Data is based on round-trip flight searches on KAYAK over the past month.

The cheapest ticket to Caribbean from Hartford found in the last 5 days was to Punta Cana, at $216 round-trip. The most popular route is from Hartford (BDL) to San Juan Luis Munoz Marin Intl Airport (SJU), and the cheapest round-trip airline ticket found on this route in the last 5 days was $246.

What is the cheapest time of day to fly to Caribbean?

The average price for all round-trip flights from Hartford to Caribbean depending on the time of departure, clicked by users on KAYAK in the last 2 weeks.

The cheapest time of day to fly to Caribbean is generally in the afternoon, when round-trip flights cost $344 on average. Morning departures are around 12% more expensive than evening flights, on average. The most expensive time of day to fly to Caribbean is generally in the morning, which is peak travel time and where the average cost of a ticket is $399.

Can I save money by flying with a layover from Hartford to Caribbean?

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

No, with an average price for the route of $424, prices are generally cheapest when you fly direct.

What is the cheapest month to fly from Hartford to Caribbean?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Hartford to Caribbean, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Hartford to Caribbean is May, when tickets cost $376 (return) on average. On the other hand, the most expensive months are December and November, when the average cost of round-trip tickets is $491 and $456 respectively.

What’s the cheapest day of the week to fly from Hartford to Caribbean?

The average price of all round-trip flights from Hartford to Caribbean clicked on KAYAK for each day over the last 12 months.

If your flying dates are flexible, you should consider flying to Caribbean on a Sunday, as we generally find the cheapest rates on that day for this route. On the other hand, Friday is the most expensive day to fly from Hartford to Caribbean. For your return ticket, we recommend flying on a Friday and avoiding Sundays for the best deals.

How far in advance should I book a flight from Hartford to Caribbean?

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from Hartford to Caribbean, removes the top 0.1% to account for outliers, and then takes the average of all the values for each week.

To get a below average price on the flight from Hartford to Caribbean, you should book around 1 week before departure. For the absolute cheapest price, our data suggests you should book 5 weeks before departure.

Good to know

Low season

September

Cheapest flight

$118
Best time to beat the crowds with an average 11% drop in price.
Most popular time to fly with an average 15% increase in price.
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 from Hartford to Caribbean 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 from Hartford to Caribbean with an airline and back 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 from Hartford to Caribbean up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

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 $181 one-way - $312 round-trip
  • 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).

Reviews of the 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.
7.8
DeltaOverall score based on 8482 reviews
8.1Boarding
7.8Comfort
7.2Food
7.8Entertainment
8.5Crew
Airline reviews

My son’s suitcase was left behind at SFO and did not make the flight.

6.0 GoodJorge, Jul 2026
SFO - GDL
Read more Delta reviews

My son’s suitcase was left behind at SFO and did not make the flight.

Seats were not bad enough and uncomfortable good legroom in the emergency exit row we were in, but we were forbidden to hold my grandson on my lap for a little while, and the stewardess passed us saying it was against regulations which makes little or no sense when you’re 36,000 feet. The food snacks were really bad. Tasteless tasted like wallpaper, but we’re supposed to be protein bars, and the announcements were all completely incoherent because of the noise of the airplane and the lowness and crackly nature of the PA system.. this was disgraceful. No one in our party could understand a word of what the captain or the flight attendant were saying —not a word! The landing was a little hairy in a pretty stiff crosswind -we bounced before the plane stabilized on the runway

Chaotic boarding at these gates, multiple gates squeezed in at the very end of a concourse, behind a restaurant. Agents gave up on boarding by individual zones. Flight itself was uneventful, which is all we hope for any more.

Unprepared to rebook a flight of people. Uncommunicative. When I received updates in the app it was well after the announcement in the hold room. Offered a single $12 meal voucher, not enough for a sandwich at DEN, for a 17 hour delay. No one was able to explain their meal or hotel reimbursement policy for this cancellation, just handed a card to call the Help desk. My previous flight went through several delays and was finally cancelled, without explanation. The customer help desk closed while there was a long line. I then waited in line for a gate agent almost an hour while simultaneously on hold and trying to text with a remote Delta agent. Communicating with the text agent was almost impossible; they could not find any flights that got me back to my original city before the following evening. Kept offering itineraries that did not get me back to my origin airport or involved additional layovers. In 50 minutes on hold, never got through to an agent by phone. Finally spoke to one of the gate agents who was able to rebook on a red eye that had only one stop and got me back in the afternoon the next day, rather than late evening. Later by email, Delta offered 10,000 loyalty points for the inconvenience of the cancellation. The crew on the red eye flight were delightful. I don’t remember any food or entertainment on that flight.

Flight team was great and we even arrived ahead of plan!

It was good delayed again but once on board the flight crew were very good the entertainment and wifi worked on this plane and we were offered snacks and drinks

The boarding agent guy in Lexington on 7/23 that boarded the flights to Atlanta is very rude for working in customer service. I know there were delays but he was dismissive rude and arrogant. Most native Kentucky residents are nice and very cordial he needs to eat a big ole piece of humble pie. I watched him be rude to several people and as much as he could of filled up a delayed flight to save you money and he was so rude to people it was ridiculous. Next no water or snacks on short flights is awful 1st you delay a flight then do not even offer water on the flight.. No thanks I like delta better but I travel ever week and to be treated like this might as well fly American at least they offer water and have better rewards.

Flight was delayed multiple time and for more than 1 hr. My onward flight from BOS to MCI was also delayed. These delays have caused me so much inconvenience and Delta does nothing to ensure flights take off on time. No one knew why the inbound flight was delayed and what was the issue.

Everything was good except when we're on a 6 hour flight at dinner time and all they offer as part of the fare are little bags of junk food, it's disappointing. Bring back food service without an added price.

It's OK. Engine was noisy. The flight was super late. I mean 4 hours late. That is unheard of.

Wonderful flight! The crew was good, check-in was good and orderly and the flight was uneventful and good.

Gluten free snack options and meals that offer both gluten free and dairy free.

The pilot was late so we didn’t take off til almost 2 hours late.

The SFO lounge closes at 12 midnight. My flight took off at 2AM

Not a bad flight but a long delay boarding and taking off due to the pilot not arriving on time.

The experience with United Airlines was excellent; however, the experience with Houston Intercontinental Airport (IAH) was horrible. Although our flight departed from Terminal B, we had to go through security in Terminal C and then get on a train for travel to Terminal B. Additionally, there was significant walking required to get to the boarding location.

Delayed 2 hours while stuck on the aircraft. If the luggage was properly loaded the first time we probably wouldn’t have been delayed at all

Overall a good experience, but no wifi available for free or for purchase and we got wet from condensation or other water source during descent.

Plane didn’t even make it off the ground. We all had to get off and walk to a different terminal (lots of confusion) to get on a different plane. Landed fairly late, connections missed.

Awful…flight was delayed more than 12hrs, missed all connections to Fort Wayne, IN, had to get flight to another city 2 hours from my destination, flight was again delayed by 40 mins because they did not have enough fuel, again missed a connection, finally arrived in Indiana at 11pm…but before my 2 hour drive home, ay, no Five That Our Luggage Never Made On The plane and Still In Chicago

Patrons with larger bags were asked to check the bags when boarding. Seems like the most effective, and least costly way, way to successfully use the cramped space.

Like all planes recently, entertainment is achieved by giving the patron free WiFi and letting them stream shows via the screen on a phone or tablet.

Worst communication. Delayed boarding for two hours without a single announcement until hour 1 had passed - on time status showing until our flight was supposed to takeoff and the crew had already walked away. No one was boarding. Disgusting part of DFW overcrowded with no AC on a 97 degree day. Then the first app update is that we’d take off in 15 mins… but again no one had boarded a full flight. No announcement in the terminal so everyone is just crowded around a disgusting place with no info for over an hour which turned into two. This was an overfill flight and a disgrace to passenger decency all while likely just trying to fix their own issue of overbooking. The worst airline at the worst airport.

My seat had a worn out cushion, which made it a bit uncomfortable. Other than that, the flight was excellent.

the first flight smelled like urine Ac didn’t work pathetic experience

The flight was delayed multiple times. I was autobooted and placed in the center seat in the last row of the plane.

Am still mad at American airlines. You should know it's us travel nurses who are your customers and you treat us like nonsense it's not ok. American airlines took my money, no refund for whatsoever. A trip that was of 466 and I paid 466 and 833 then they chose for me where to sit and refund my seat choices and gave me expensive seats for 79 USD. Kayak doesn't help at all after booking you are on your own. Skyscanner is better

Terrible experience with baggage claim at CLT. Posted as arriving at belt 4 and screen there showed the flight. Waited for over 1.2hrs before someone randomly came by and said the bags for that flight had been dropped at CD1 an unknown time ago. There was no notification in the app, on the screens or by any airport personnel prior to this time. Waiting 1.2 hrs after a 2 hr flight for a bag you paid $40 extra to check is infuriating and disappointing.

On the new 319 NEO? seatback entertainment system did not work even when the flight attendant rebooted it. At least I had my cell phone to connect with wifi.

Delay. Flight was delayed in Washington.knew that connection was impossible as not enough time to switch terminals. The steward would not let me stay the night. So forced to Dallas.late night, after 10pm.hotel checkin was one hour. Passengers lined up only one girl to checkin at comfort inn. No food availability at that time. Had to leave early at 6:30 am to catch a flight at 8:45. Stressfull.

Plane was delayed multiple times. I would like to request a refund. Was due to arrive Thursday evening ended up arriving Friday morning.

The seats were roomier than other airplanes I’ve been on.

The crew and the pilots. The pilots were amazing. The landing in Cancun was excellent.

The security line at JFK was one of the longest I’ve ever experienced - probably 45 minutes. I don’t know if JetBlue has control over it, but it detracted from the overall experience. Entertainment had good options, but the volume control was a bit small to tap on and the screen had a fair amount of interference blips. Clearer picture would have been better.

I liked the entertainment on JetBlue, the service from JFK to JAX was terrible at best

I usually dont fly JeTBlue and I dont think I will ever do it again. The flight was delayed fee time, nobody was giving us any info at at the airport, gate changing, the slowest and poorly organized boarding ever, rude staff.. huh

The flight was delayed. I upgraded to more room. I can't imagine how small the regular seats are I haven't upgraded for my return flight yet.

see my previous response about being kicked off the flight and having to fly the next day, ruining a planned vacation tour.

Like the variety of entertainment options. One crew member was a little on the rough/rude side. Boarding was a mess, attendants didn't do a great job of helping with the luggage storage and it delayed us a couple of minutes.

The flight was delayed after already taxiing from the gate due to a malfunction. After 3 hours we were told the flight was canceled. The next flight available was Sunday. My daughter and I stayed overnight in the airport due to this issue. I was given a $12 meal voucher. Unacceptable

Frontier feels like a family I Worked for Eastern Airlines back in the day and I felt the family vibe that I had then. Thank you

Terrible. Delayed my family flight for several hours affecting family plans

During the flight I suddenly felt very sick, and no one from the crew even tried to help me or check on my condition. They seemed completely indifferent and showed no concern for my well-being. I was very disappointed by the lack of care and compassion. I hope the airline improves its customer service and trains its crew to respond better when passengers need assistance.

Tiny seats, no entertainment, no amenities, delays, they charge for carry on and their allowed personal item is smaller than in other airlines.

The seats are tiny and they don’t recline. The planes are dirty and very small. You have to pay for carry on and even the personal item that you’re allowed is smaller than with other airlines. Flights are usually delayed and there’s no screens or any amenities or entertainment.

Flight was delayed but it was very smooth. Crew was very nice. Seats are uncomfortable but ok.

Flight was delayed and then my second leg was completely canceled. Had to get a refund

The flight was great . But you only had one vegan item on the whole flight and someone prior to me took it . I was so disappointed cause I came in from the flooded area and couldn’t pick up anything prior to my flight .

I really didn't like anything. Paid for my checked luggage online ($79) and then was told that I would have to paid another $79 for my carry on. Was not allowed to enter the terminal until 3 hours before my flight and when I finally was allowed to check my bag and enter, my flight was delayed 3 times. When I finally landed, we were all instructed to "run off the plane" as they had to do a quick turn around to Las Vegas. Me and several of my flying companions will never fly Frontier again.

I paid for the upgraded bundle. Was worth it! Great experience round trip!

Everything you need to know for your flight to Caribbean

Information on your arrival and departure airports