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Find cheap flights from Hartford to Caribbean from $69

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 5/26. 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
Tue 6/4
Tue 6/11

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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$230
Montego Bay
Montego Bay2 stops$354
Santo Domingo
Santo Domingo1 stop$215
Oranjestad
Oranjestad1 stop$443
Nassau
Nassau1 stop$288
Kingston
Kingston2 stops$433
Simpson Bay
Simpson Bay2 stops$376
Providenciales
Providenciales1 stop$413
Port of Spain
Port of Spain2 stops$597
Bridgetown
Bridgetown1 stop$488
George Town
George Town1 stop$487
Aguadilla
Aguadilla2 stops$304
Willemstad
Willemstad1 stop$502
St. John's
St. John's2 stops$682

Good to know

Low season

September

High season

February

Cheapest flight

$69
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 $99 one-way - $176 round-trip
  • Morning departure is around 10% 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 10826 reviews
8.6Crew
7.9Comfort
8.0Entertainment
8.2Boarding
7.4Food
Airline reviews

Very frustrated with boarding gate crew. She announced the plane was small and they would be limiting us to one item to carry on. Not a problem for me as I understand the tiny planes have limited space!! Not the case here! It was a rather large plane and had plenty of room for bags! So because I don’t want to be one of “those people” who ignores the request to check a carry on I did so asking if I would be able to pick it up at the bottom of the ramp on arrival in Knoxville to which she responded “yes”! Then I watched as every other passenger held onto their 2 items and boarded!! Then when we arrived in Knoxville our 2 carry ons had been put with all the other luggage and we had to go to baggage pick up and wait for all the big checked bags to come off the carousel! So she lied!! Frustrating. Next time I won’t be so nice!

8.0 ExcellentCynthia, May 2024ATL - TYS
Read more about Delta reviews

Very frustrated with boarding gate crew. She announced the plane was small and they would be limiting us to one item to carry on. Not a problem for me as I understand the tiny planes have limited space!! Not the case here! It was a rather large plane and had plenty of room for bags! So because I don’t want to be one of “those people” who ignores the request to check a carry on I did so asking if I would be able to pick it up at the bottom of the ramp on arrival in Knoxville to which she responded “yes”! Then I watched as every other passenger held onto their 2 items and boarded!! Then when we arrived in Knoxville our 2 carry ons had been put with all the other luggage and we had to go to baggage pick up and wait for all the big checked bags to come off the carousel! So she lied!! Frustrating. Next time I won’t be so nice!

It was a good experience except when boarding a female flight attendant did not go out of her way to assist my teenage daughters in finding space for their carry-ons after their compartments were full.

On time departure, smooth trip, flight attendant told through passengers the gate we would arrive at and the gate our outbound flight was departing from. Early arrival

Checking in at the airport the agent only booked the first keg of my trip and had my checked luggage going to the airport with a layover! Never was issued a boarding pass for the second leg or received sticker fir my checked bag. All was well in the end! Delta agents helped to resolve the situation!!!

Delayed due to an ill passenger after loading. Not preventable on Delta's part. Was in first class. The seats are becoming worn and detaching from their velcro attachments. Only got snacks on flight. The attendant was not the friendliest.

I would fly again the whole experience was great. The only feed back I can give that they don't do that American Airlines does is the crew there is more humorous with boarding and thank their passengers. It makes it more fun to fly with them. I would however fly Delta again.

Big plane, long flight, absolutely no leg room and basically non existent air! I am 5”4’ and always travel Main Cabin, I was miserable on this plane and could barely move when we arrived in Cabo due to the cramped leg area!

From Atlanta to Cabo I would have hoped on a plane that size I would have been able to breathe and wiggle my feet a little! The leg room in that plane is non existent and I am only 5”4’. And the air vent either wasn’t working very well or just could not blow air from the ceiling to the seat area as I was suffocating through the entire flight! And please don’t say I would have been more comfortable in first class because I cannot afford those rates and have always travelled Main Cabin without issues !

The pilots were good. Disappointing when planes don't have electrical ports

I liked the piloting of the aircraft. Very disappointed about lack of electrical ports. Also, although a short flight. there was enough time to hand out snacks to comfort + seats as was done for first class.

Great. Loved that there was WiFi on flight to keep in touch and excellent service of beverages and snacks.

Business class is great. New airplane, very comfortable, better than some of the major airlines I am used to

Terrible. Flight was cancelled due to the weather in the east and sout east(florida). Did not get any compesation of any kind. According to them, it was not under their control so I lost all the money paid for the 2 fairs from Raleigh, NC to Orlando, Fl.

great flight. Pilot was communicative, flight attendants were excellent. Really nice experience except my tv didn’t work.

Overall, the flight was better than the flight I took to go to Florida, which had a bunch of problems. The crew is really nice and the plane was new so it had a small problem when we were on the runway, but the flight itself was great. They even made some time back up, which is always a good thing.

at the time for boarding the lady just call Group A and no other goups and everybody from A to F go inside without the right turn,and when we get in theres no more spsce for carry on , the ones that get in at not correct group from the back occupy our space !!!!! a mess !!!!

There were multiple delays but JetBlue tried to make the boarding and departure process as quick and efficient as possible. The crew was as detached from reality as could be, meaning: not very friendly and just doing things by the numbers.

I had back trouble prior to my flight and everyone was great about helping me.

Jetblue needs to improve on Onboarding as it seems to always be behind on departing. It never leaves on time. I would recommend to have an earlier Onboarding in order to leave on time and respect your customers time as well.

40 minute delay before take off after boarding flight. Bright lights throughout night flight due Issues with light panels. In flight Entertainment nonfunctional

Great crew. Very comfortable business seats with nice bedding. Good food. We were delayed to let late passengers on the flight, but otherwise great experience.

Great crew. We were delayed so that late passengers could get on the flight. Love the bedding in business class. Good food. Great experience.

The CX617 from HK to BKK was delayed more than 1.5 hours.

Horrible - they lied to me about baggage & boarding, even though I specifically spoke to their agents the day before my flight about my issue. When I showed up they did not let me board and stranded me at my airport until I bought a new flight with money I did not have to spend.

I was in business class. There was an excellent headset. But half an hour before arrival they collected them! The rest of the trip I had to use a cheap earphone. There must be a better way to protect the headphones.

All four American Airlines flights I took in last seven days were delayed. Caused me loads of problems, missed meetings, loss of time and money.

American cancelled our flight home. Zero option for hotel, alternative transportation and took 3 hours to find our bags so we could take a 3 hour UBER ride home on our dime. Never flying AA again.

They gave my seat away although it was a connecting flight with them and the flight was a bit delayed.

Flight was cancelled had to move to another gate late again no internet paid for the month and never can use it waste of money

Not being able to purchase my check in baggage online was a negative.

The crew was not great or professional. It seemed like they didn't really want to be there. A true lack of effort for accommodating customers.

Everything was really good but the seats are not very comfortable.

I paid for WiFi, but it (WiFi) was very very slow, will never take again! Impossible open Utube 😤😤😤

I had no legroom, although I paid for extra legroom. I could barely put my bag in front of my feet and under the seat. The Wi-Fi was horrible. In fact the flight attendant said that they had to reboot it and see if it was going to work and never did.

The guy with severe body odor sat next to me. For the whole duration of the flight it was a torture. The airline should have better policy on limiting people with bad body odor to board the flight. Passengers should not be the ones to endure bad odor for the whole duration of the flight. The airline should be e the one to ensure decent air quality for ever passenger.

Overall it was a miserable experience... I will never fly spirit for more than a 3 hour flight or overnight.

The boarding attendant was slightly rude when I asked about checking our stroller. Made me feel like I was bothering her.

My wife and I are both handicapped and at boarding they upgraded us to a seat closer to the front rather than all the way towards the back. Much appreciated.

Not much seat room, but that was unexpected. But the seat headrest was very uncomfortable.

First the good, everyone was friendly and efficient. Flight was smooth and plane was very clean and new. Now the bad, seats have almost no padding on your behind. I was in exit row so I had tons of leg room for a 6' 2" bean pole with long legs. Everything was extra - water, soda, snacks everything besides oxygen. Ya get what you pay for, and my flight was cheap as you could ever want it, so no worries.

Not good 😐 Over priced baggage fees Small hard seats No wifi or entertainment options 😕

Didn't like anything!! Horrible flight. Small seating area and hard seats. Butt was sore after 2 hour flight to Seattle No entertainment or free refreshments No wifi or USB charging receptacles to charge phone entoute like other airliners Luggage rates were 3 times as much as competitors. Difficult to navigate online luggue process to pre pay before flight Overall bad experience WILL NEVER RIDE OR RECOMMEND FRONTIER TO FRIENDS OR FAMILY MEMBERS!!! THIS IS A SHAME!! MOST MESERIBLE FLIGHT OF MY LIFE!! AND I THOUGHT SPIRIT WAS 👎 YOU GOT THEM BEAD HANDS DOWN!!

Flight was a little late taking off. Seats are too upright, no ports to charge devices, no wifi, no entertainment

Six hour delay. Poor customer service. No voucher. Bad communication. Missed important appointments.

Our flight was delayed an hour, then when we got to board our flight finally, we were waiting in our seats for take off for 45 minutes before it was communicated that there was a maintenance issue therefore we waited on the plane for over an hour while that was resolved. We did not get to Phoenix until almost 3 hours after we were originally supposed to. This was the first and last time I will be flying Frontier.

Flight was canceled with little warning. Flight was rebooked through Ontario, California and connecting flight was delayed by over three hours. Frontier is living up to their Greyhound of the skies reputation for sure.

I purchased a carry on bag online…was supposed to cost $72 but after a whole slew of bs charges, the total was over $175.00. Because of these hidden charges, I will not even consider flying Frontier ever again. It’s just not worth the hassle. I’m scratching this company off my list forever.

Flight was OK. Seats were good no cell phone charges on the plane no TVs or entertainment.

There were 3 leg for the trip and each leg was delayed by 90 minutes or more. The boarding process takes forever with people waiting on the jetway even though most folks do not have carry-on. The whole process is poorly managed.

Flight cancelled and was told by a rude gate agent that they don’t accommodate on other airlines. Had to wait 5 hours for a connecting flight that had a 7 hour layover. Would not allow bags to be checked early so we couldn’t go through security .Had to rent a car for the afternoon to store bags and get a meal. Also incurred a hotel fee. No apology or reason given for the cancellation- just rudeness.

Book cheap flights from Hartford to Caribbean

Recent round-trip flight deals

5/17Fri
nonstopFrontier
3h 47mBDL-SJU
5/31Fri
nonstopFrontier
3h 48mSJU-BDL
$136
5/26Sun
nonstopFrontier
3h 47mBDL-SJU
6/1Sat
nonstopFrontier
3h 48mSJU-BDL
$137
5/26Sun
nonstopJetBlue
3h 51mBDL-SJU
5/30Thu
nonstopJetBlue
4h 06mSJU-BDL
$219
5/26Sun
nonstopJetBlue
3h 51mBDL-SJU
5/31Fri
nonstopJetBlue
4h 03mSJU-BDL
$239
5/29Wed
3 stopsSpirit Airlines
34h 55mBDL-SJU
6/5Wed
3 stopsSpirit Airlines
31h 28mSJU-BDL
$257
5/27Mon
2 stopsSpirit Airlines
21h 29mBDL-SJU
5/30Thu
2 stopsSpirit Airlines
31h 28mSJU-BDL
$270
5/27Mon
1 stopAmerican Airlines
14h 33mBDL-NAS
6/3Mon
1 stopAmerican Airlines
9h 55mNAS-BDL
$288
5/26Sun
1 stopDelta
6h 28mBDL-NAS
5/31Fri
1 stopDelta
6h 31mNAS-BDL
$289
8/24Sat
2 stopsAmerican Airlines
7h 17mBDL-NAS
8/27Tue
1 stopAmerican Airlines
7h 07mNAS-BDL
$292
9/14Sat
1 stopDelta
6h 34mBDL-PLS
9/18Wed
1 stopDelta
7h 12mPLS-BDL
$441

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Recent one-way flight deals

5/26Sun
nonstopFrontier
3h 47mBDL-SJU
$69
5/12Sun
nonstopFrontier
3h 48mBDL-SJU
$70
5/14Tue
2 stopsSpirit Airlines
19h 22mBDL-SJU
$72
5/28Tue
3 stopsSpirit Airlines
34h 55mBDL-SJU
$87
5/28Tue
1 stopAmerican Airlines
14h 33mBDL-NAS
$90
5/14Tue
1 stopAmerican Airlines
10h 16mBDL-SJU
$113
6/4Tue
1 stopJetBlue
6h 55mBDL-SJU
$166
5/26Sun
1 stopDelta
8h 19mBDL-SJU
$167
5/13Mon
1 stopDelta
10h 11mBDL-SJU
$179
5/17Fri
nonstopJetBlue
3h 51mBDL-SJU
$182

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Last minute flights from Hartford to Caribbean

Last minute flight, train and bus deals

5/7Tue
nonstopFrontier
3h 48mBDL-SJU
5/11Sat
nonstopFrontier
3h 59mSJU-BDL
$180
5/9Thu
nonstopFrontier
3h 48mBDL-SJU
5/16Thu
nonstopFrontier
3h 48mSJU-BDL
$201
5/8Wed
nonstopJetBlue
3h 51mBDL-SJU
5/9Thu
nonstopJetBlue
4h 06mSJU-BDL
$292
5/10Fri
multi-stopAmerican Airlines
8h 29mBDL-SJU
5/10Fri
multi-stopAmerican Airlines
16h 16mSJU-BDL
$294
5/8Wed
multi-stopAmerican Airlines
14h 36mBDL-SJU
5/10Fri
multi-stopAmerican Airlines
15h 14mSJU-BDL
$298
5/8Wed
nonstopJetBlue
3h 51mBDL-SJU
5/14Tue
nonstopJetBlue
4h 06mSJU-BDL
$312
5/7Tue
multi-stopDelta
8h 19mBDL-SJU
5/8Wed
multi-stopDelta
8h 41mSJU-BDL
$334
5/7Tue
multi-stopSpirit Airlines
9h 39mBDL-SJU
5/10Fri
multi-stopSpirit Airlines
31h 03mSJU-BDL
$348
5/7Tue
multi-stopSpirit Airlines
9h 39mBDL-SJU
5/14Tue
multi-stopSpirit Airlines
26h 48mSJU-BDL
$400
5/7Tue
multi-stopDelta
10h 19mBDL-SJU
5/10Fri
multi-stopDelta
8h 41mSJU-BDL
$419

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