$84 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 5/29. 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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Flights Deals

Best Caribbean Flight Deals from Hartford

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

Punta Cana
Punta Cananonstop$216
Santo Domingo
Santo Domingo1 stop$349
Montego Bay
Montego Baynonstop$240
Oranjestad
Oranjestad1 stop$380
Nassau
Nassau1 stop$401
Kingston
Kingston1 stop$371
Simpson Bay
Simpson Bay1 stop$364
Providenciales
Providenciales1 stop$434
Bridgetown
Bridgetown1 stop$445
Port of Spain
Port of Spain1 stop$507
George Town
George Town2 stops$438
Willemstad
Willemstad1 stop$545
St. John's
St. John's1 stop$444
Puerto Plata
Puerto Plata1 stop$464
Aguadilla
Aguadilla1 stop$304
Punta Cana
Punta Cananonstop$216
Santo Domingo
Santo Domingo1 stop$349
Montego Bay
Montego Baynonstop$240
Oranjestad
Oranjestad1 stop$380
Nassau
Nassau1 stop$401
Kingston
Kingston1 stop$371
Simpson Bay
Simpson Bay1 stop$364
Providenciales
Providenciales1 stop$434
Bridgetown
Bridgetown1 stop$445
Port of Spain
Port of Spain1 stop$507
George Town
George Town2 stops$438
Willemstad
Willemstad1 stop$545
St. John's
St. John's1 stop$444
Puerto Plata
Puerto Plata1 stop$464
Aguadilla
Aguadilla1 stop$304

Cheap Flight Deals from Hartford to Caribbean (BDL-0CB)

 
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.

Recent round-trip flight deals from Hartford to Caribbean

Recommended round-trip deals departing in the coming months from the most popular airlines that fly from Hartford to Caribbean.
Discover the best prices for you by selecting your travel dates on KAYAK.
Spirit Airlines Logo
9:15 am - 4:46 pmBDL-SJU
7h 31m1 stop
Spirit Airlines Logo
5:41 pm - 8:10 amSJU-BDL
14h 29m1 stop
$184Spirit Airlines
Find Deal
Thu, Jul 24 - Fri, Aug 1
Spirit Airlines Logo
9:15 am - 4:46 pmBDL-SJU
7h 31m1 stop
Spirit Airlines Logo
5:41 pm - 8:10 amSJU-BDL
14h 29m1 stop
$185Spirit Airlines
Find Deal
Fri, Jul 25 - Sun, Jul 27
Frontier Logo
11:38 am - 3:33 pmBDL-SJU
3h 55mnonstop
Frontier Logo
6:36 am - 10:38 amSJU-BDL
4h 02mnonstop
$197Frontier
Find Deal
Mon, Jun 2 - Thu, Jun 5
Frontier Logo
4:59 pm - 8:53 pmBDL-SJU
3h 54mnonstop
Frontier Logo
11:55 am - 3:59 pmSJU-BDL
4h 04mnonstop
$215Frontier
Find Deal
Fri, May 16 - Tue, May 20
JetBlue Logo
8:03 pm - 11:56 pmBDL-SJU
3h 53mnonstop
JetBlue Logo
8:35 pm - 12:31 amSJU-BDL
3h 56mnonstop
$258JetBlue
Find Deal
Thu, May 29 - Wed, Jun 4
JetBlue Logo
6:00 am - 9:54 amBDL-SJU
3h 54mnonstop
JetBlue Logo
7:00 am - 10:53 amSJU-BDL
3h 53mnonstop
$260JetBlue
Find Deal
Tue, Aug 26 - Mon, Sep 1
Delta Logo
6:00 am - 4:18 pmBDL-SJU
10h 18m1 stop
Delta Logo
2:28 pm - 11:46 pmSJU-BDL
9h 18m1 stop
$279Delta
Find Deal
Wed, Oct 15 - Thu, Oct 30
Delta Logo
6:00 am - 4:18 pmBDL-SJU
10h 18m1 stop
Delta Logo
2:28 pm - 10:03 pmSJU-BDL
7h 35m1 stop
$307Delta
Find Deal
Tue, Oct 14 - Wed, Oct 29
American Airlines Logo
7:20 pm - 11:10 amBDL-SJU
15h 50m1 stop
American Airlines Logo
7:15 am - 10:43 pmSJU-BDL
15h 28m1 stop
$329American Airlines
Find Deal
Wed, May 28 - Tue, Jun 3
American Airlines Logo
5:06 am - 2:40 pmBDL-SJU
9h 34m2 stops
American Airlines Logo
5:25 am - 3:51 pmSJU-BDL
10h 26m1 stop
$349American Airlines
Find Deal
Tue, May 13 - Fri, May 30
Useful Info

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?

The cheapest price for flight routes found by users searching on KAYAK in the last 2 weeks for round-trip flights from Hartford to Caribbean.

The cheapest ticket to Caribbean from Hartford found in the last 72 hours was to Montego Bay, at $123 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 72 hours was $131.

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 January, when tickets cost $221 (return) on average. On the other hand, the most expensive months are December and June, when the average cost of round-trip tickets is $406 and $297 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 Tuesday, as we generally find the cheapest rates on that day for this route. On the other hand, Sunday is the most expensive day to fly from Hartford to Caribbean. For your return ticket, we recommend flying on a Wednesday and avoiding Mondays 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 3 weeks before departure.


Good to know

Low seasonSeptember
High seasonDecember
Cheapest flight$84
Best time to beat the crowds with an average 19% drop in price.
Most popular time to fly with an average 30% 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.

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

    The cheapest time of day to fly to Caribbean is generally in the evening, when round-trip flights cost $257 on average. Morning departures are around 48% 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 $380.

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 $133 one-way - $260 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).

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 7934 reviews
7.3Food
8.2Boarding
8.5Crew
7.9Entertainment
7.9Comfort
Airline reviews

Our bag was lost so that made unnecessary chaos On our trip

6.0 GoodBarbara, Apr 2025JFK - FCO
Read more Delta reviews

Our bag was lost so that made unnecessary chaos On our trip

Delta is my preferred airline. I've traveled with them for years. On time in most cases, good communication, easy to use app. Most planes are pretty nice. I was on a CRJ 700/900 however, which was pretty badly aged inside and needed a refresh. No infotainment, unreliable wifi, best to download before boarding or bring a book. Food choices are really just snacks on this flight, nice variety but about what you'd expect. Great staff and prompt in departure and early arrival too. Overall quite satisfied.

Crew was friendly Love the entertainment in the seat head rest.

Delta flight was on time, seats were comfortable, and crew was nice.

This had nothing to do with Delta… The flights were on time and flawless. The service was excellent. We purchased seats in (aisle/middle) comfort plus since this was a cross country flight. Unfortunately, the woman seated at the window was 300+ pounds and, as might be expected, covered up about a third of the middle seat also. there was absolutely nothing that Delta could have done about that… I just don’t know what the answer should be. If you purchase a seat, you should should be able to use the entire seat and not just the portion that someone else is not sitting/oozing in. Disappointing…there should be something that could be done….I'm just not sure what solution could be.

Delayed take-off. Very small plane so very scary with lots of bumps during the flight. Would never fly Delta on short flights in small 80 seaters plane again! Felt relieved when landed.

The worst part was I was NOT allowed in the lounge even though I was holding a first class ticket and have a premium American Express card. I have flown Business or First Class with many airlines. Delta is the ONLY one who does not extend this courtesy to anyone except people who hold the very expensive American Express card. As a result, I won’t fly Delta if I have any other choice.

It was an overnight flight and I desperately needed coffee before we landed, but Delta does only one beverage service, and that is shortly after takeoff, not before landing at 5 am.

A little bumpy ride . No food was being provided due the the turbulence. That was ok it was a short flight to my standards.

Simply outstanding. Their new lounge for Delta One customers is a cut above the rest.

Everything is good except the dinner and breakfast. The sandwich is very delicious. Toilet is clean, I only use one of them. Flight attendants are very nice. 👍👍

A bit rush for transit. Food and entertainment are not available

Boarding was a little difficult. The gate area at O'Hare was very small and crowded due to multiple gates in the area. Could not hear the intercom, so had to rely on signage to see when my group was boarding and the signage was blocked by passengers standing in the gate. Flight was great and we arrived in Montreal on time.

Multiple delays and not straight answer from the United team

For economy, it was very good. Staff was great, they even let some of us change seats for more leg room... Put an empty seat between us which was fantastic for a 12hr flight. Onboard entertainment was excellent, I think over 200 choices of movies/tv/etc The bad was the barely/nonfunctional wifi that cost either $16.99 or 1700 miles (full flight). It was atrocious... Definitely the worst of the last 3 long haul major airlines I was on the last few months.

Stewardess spilled orange juice on my clothes/seat no help no apology just threw napkins at me to clean the mess up. Not Happy.

Smooth flight. Boarding was chaotic. Could not hear the gate agent over the intercom. People were lined up in the wrong lines. Groups one and two were told to board through line one and group 3 through line 2. All very confusing. Once in the air, the flight was smooth. There was no entertainment option on this aircraft, even though it was a larger aircraft.

The plane pushed back from the gate on time. However, it stopped on the ramp, and we waited for over 20 minutes before the aircraft pulled back to the gate. Apparently, something of importance had to be removed from the aircraft by the gate agent. I found this to be odd. The delay was not significant, but I felt that whatever was on the aircraft that had to be taken off, should’ve been done before we pushed back from the gate.

I didn’t get on plane. Passport being processed by consulate with visa application. Tried to cancel through underpricer after purchasing cacelling for any reason. No dice, they are thieves.

Electric plugs didn't work. Entertainment system wasn't working

Excellent from start to finish. All staff members were amazing!

Excellent. Although they used to greet me as a mosaic member and provide a free drink, early boarding helps me to keep coming back to JetBlue.

Cancelled flight with no specific instructions to get a boarding pass for another flight. The whole flight of people were in line for an hour because there was only 1 person to help at the desk. This was unusual for JetBlue.

It was too hot in the cabin. The AC did not help.

Except for the 28 minute delay leaving and the earlier reschedule to a later takeoff time the flight was good.

Loved the leg room and tvs screens on the seats and free WiFi. Wish the price was lower and could save by rebooking

No music app working: no economy meal on five hour flight; hour on tarmac at the end waiting for a gate. Flight itself was smooth and easy.

It took 1-1/2 hours to get our luggage after we landed. That to me is unacceptable

The flight was delayed for 4 hours. Once onboard the crew was wonderful.

Overall was excellent. Will definitely us JetBlue in the future.

Several delays. Next flight was worse. Did not arrive home until 2am PT

Very helpful ground crew after an earlier flight delay and being rebooked on a different flight.

Everything about the flight was lovely…We left early, arrived early, cabin crew were efficient and helpful. Flight was easy and most pleasant.

First world problems, but still… We were seated in first class and asked for a cocktail on a very short, 50 minute flight. After our drink order was taken, a half hour went by, and we noticed that every other person in the small plane had been served except for us. We got up to ask about it, the drinks finally came, then were taken away three minutes later since the flight was so short. Really strange situation, on the other hand, we were in Utah.

We missed our flight. The boarding pass had the wrong gate and by the time we received the text from Kayak, our flight was already gone. I’ll never use Kayak again and will go direct to the airlines in the future.

Boarding took forever, the plane was cramped and cold, and the seatbelt song came on constantly throughout the red eye flight with a loud pre-recorded message playing each time

Cabin felt crammed Snacks are lame But crew was super efficient getting us out on time despite delay

Took off on time and successfully avoided weather that looked to be a problem along the way

There were five broken seats on the plane. The crew was very rude in telling people they had to get off the plane and get a flight the next day. No call for volunteers, but telling people they had to get off. One woman was flying with her elderly mother and daughter and was told she had to leave or all three had to leave. Fortunately, a volunteer offered to stay. The situation was handled poorly.

The flight to Tokyo AA61 took off about two hours late, but then had to turn back. By that time the crew had to be replaced. Then they kept promising to take off in an hour, then in 3, then switch to the next day.

The reps working at the airport counter were dumber than a second coat of paint.

My costume jewelry was stolen out of my bag. Got to airport and my bag weighed 45 pounds- 5 pounds over cost me $100 Long lines in tier one. No entertainment No WiFi no free drinks or snacks

Not very good. Paid in excess of $400 for assigned seating for my family and that was not provided. I want that money back.

The seats were hard molded plastic covered in plastic vinyl. And the scam to charge people extra to sit together. Don’t they know we can just ask someone to trade seats. And watching the staff separate young children from parents… super classy. We had to guilt them into offering up our seats. This companies policies suck. Don’t give them your money.

The seats were awful, hard plastic covered in sheet vinyl. The airline tries to scam you into paying extra to get seat together when the flight wasn’t full. They were going to separate a family with young children but my wife who had a row to herself gave up her seat so the young mom could be with her young boys. I’m never giving this airline my money again.

It was a short flight so no food or entertainment….

Seats are uncomfortable but price is good. Guess I can put up with misery for four hours.

I’ve never traveled on Frontier before. If you want basic, no frills, friendly service at great prices then give them a fly!

Cancelled and declined to find alternatives Earlier flight is 2 days later Sent the cancellation notification very late, wish I knew earlier would have stayed to watch the Miami open final game Very disappointing service

The worst flight of my life. Never will I fly frontier again

Everything you need to know for your flight to Caribbean

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