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Find cheap flights from Hartford to Caribbean from $49

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 9/11. 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 6/8
Sat 6/15

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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$267
Montego Bay
Montego Bay2 stops$376
Santo Domingo
Santo Domingo1 stop$235
Oranjestad
Oranjestad1 stop$443
Nassau
Nassau1 stop$286
Kingston
Kingston1 stop$381
Simpson Bay
Simpson Bay1 stop$205
Providenciales
Providenciales1 stop$411
Port of Spain
Port of Spain2 stops$579
Bridgetown
Bridgetown1 stop$487
George Town
George Town1 stop$437
Aguadilla
Aguadilla2 stops$328
Willemstad
Willemstad1 stop$499
St. John's
St. John's2 stops$622

Good to know

Low season

September

High season

February

Cheapest flight

$49
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 31% 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 10778 reviews
7.9Comfort
7.4Food
8.2Boarding
8.6Crew
8.0Entertainment
Airline reviews

West Jet has a horrible boarding process and the seats have no cushion.

4.0 OkayDouglas, May 2024MSP - YEG
Read more about Delta reviews

West Jet has a horrible boarding process and the seats have no cushion.

Everything went smoothly. I didn’t like that when I booked in the main cabin my wife and I weren’t seated together. One would think when booking on an option that allows picking your seat. They would put you and your travel partner together. Had to call to get it sorted. They did fix.

The gate area was incredibly short staffed, with one representative manning 4-5 flights, which caused a 3 hr delay in boarding even though the plane was all ready to leave. Other flights also were delayed because of this. The flight crew was awesome and I feel bad for the only gate worker on call, but Delta needs to hire more employees.

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!

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

Worst situation ever! I booked my tickets for this trip on Alaska Airlines. I guess AA is a partner and we flew nonstop from Eugene to PHX on an AA jet. I had to pay for luggage from PHX to EUG. And this was an Alaska Airlines reservation paid for with Alaska airlines credit card! Got to the PHX airport and was not able to check bags because of some weird issue with the AA software. My reservation had to be the-entered by the agent. I will never pick another American Airlines flight on the Alaska Airlines website. While on vacation, I tried to upgrade our seats for the trip home. The request just buffered and never went through. I tried four times and was charged four times on my credit card. The card was charged but the seats were never changed. What a wreck!

Left from gate 30 minutes before flight. Never been late to a flight ever. It says 15 minutes before explicitly on the ticket.

I like the boarding process, it was fast. The seat doesn’t have a TV for a long flight and food wasn’t served, just snacks.

Use planes with TVs on flights over 4 hours. The free entertainment was a cheap in between solution for a very long flight that you don't even bother providing meals or decent snacks.

Even though we left CMI late, we mostly made up the time.

Delayed almost 4 hours for a 45 minute flight with no explanation.

Again, multiple delays and I eventually just canceled and drove!

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.

Flight delayed then canceled! I will NEVER fly Spirit Airlines again and will tell all my friends!

Absolutely terrible. The boarding process had zero organization. Mobs of people trying to board. People were climbing over my child's stroller with her in it. No families were boarded first. Boarding was delayed with no reasoning or notification that it would be late. We were then stuck on the plane for 45 minutes after landing. Then waited over two hours for our luggage. There was zero communication with the travelers. Never have I experienced such I professionalism and disgrace of others. Extremely disappointed.

For it to have left on time! Instead of two hours early with zero notice

Flight kept delayed from morning to late afternoon so I had to make other arrangements

Crew was nice, explained emergency protocol very well. Flight took off and arrived on time. Pilot explained the small delay that occurred with docking and providing updates. I would definitely fly spirit again.

Terrible… missed our flight due to ridiculously long time to go thru baggage check-in!

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.

I checked a bag because it was $5 less than carry on. They managed to lose my bag on a 2.5 hr direct flight! Frontier has no airport staff at baggage claim to help. As soon as I got home around 11 pm I tried to use their online system to file the claim for lost bag - system wouldn't take the # on my baggage claim ticket - said it was not the correct number. Also said that I had not checked a bag, which wasn't true - even my online boarding pass showed that I had checked a bag. Wasted about an hour on that process with no luck. Tried again in the morning - same thing. So tried online chat with Frontier bot - waited 35-40" twice to be connected to a baggage agent and it never happened. Eventually drove to PDX after work and waited 2 hrs for the Frontier ticket agents to arrive prior to the next Frontier flight out of PDX and FINALLY got some help from one of them, to take me to lost luggage area where I was able to retrive my bag. Probably took 4-5 hrs. of my time and endless frustration to get my bag. This was my first -- and LAST -- experience flying Frontier Airlines. Check-in was also extremely difficult and time consuming. The flight itself (and staff) were fine but everything else about the experience was a total disaster! The fact that Frontier literally has NO WAY to connect to a human voice for customer service (in this case for lost luggage) is the WORST!!!!!

Frontier is a crappy airline nothing about it is honest

I didn't get to do this flight l, hard to review

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.

Book cheap flights from Hartford to Caribbean

Recent round-trip flight deals

9/11Wed
nonstop
3h 52mBDL-SJU
9/17Tue
1 stop
7h 35mSJU-BDL
$147
5/26Sun
nonstopFrontier
3h 47mBDL-SJU
5/31Fri
nonstopFrontier
3h 48mSJU-BDL
$148
9/11Wed
1 stopSpirit Airlines
12h 41mBDL-SJU
9/16Mon
1 stopSpirit Airlines
10h 57mSJU-BDL
$182
5/26Sun
nonstopJetBlue
3h 51mBDL-SJU
5/29Wed
nonstopJetBlue
4h 06mSJU-BDL
$219
5/30Thu
nonstopJetBlue
3h 51mBDL-SJU
6/11Tue
nonstopJetBlue
4h 03mSJU-BDL
$239
9/7Sat
1 stopSpirit Airlines
8h 14mBDL-SDQ
9/20Fri
1 stopSpirit Airlines
10h 43mSDQ-BDL
$278
6/5Wed
1 stopAmerican Airlines
14h 10mBDL-NAS
6/12Wed
1 stopAmerican Airlines
14h 16mNAS-BDL
$286
5/27Mon
1 stopAmerican Airlines
14h 33mBDL-NAS
6/3Mon
1 stopAmerican Airlines
12h 14mNAS-BDL
$288
9/9Mon
1 stopDelta
5h 57mBDL-NAS
9/14Sat
1 stopDelta
6h 29mNAS-BDL
$289
10/25Fri
1 stopDelta
22h 53mBDL-NAS
11/2Sat
1 stopDelta
6h 29mNAS-BDL
$296

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Recent one-way flight deals

9/11Wed
nonstopFrontier
3h 52mBDL-SJU
$49
5/26Sun
nonstopFrontier
3h 47mBDL-SJU
$69
9/12Thu
nonstopJetBlue
3h 56mBDL-SJU
$79
5/28Tue
1 stopAmerican Airlines
14h 33mBDL-NAS
$90
9/18Wed
2 stopsAmerican Airlines
8h 40mBDL-NAS
$91
9/11Wed
1 stopSpirit Airlines
12h 41mBDL-SJU
$92
5/29Wed
2 stopsSpirit Airlines
11h 20mBDL-SJU
$105
5/18Sat
nonstopJetBlue
3h 51mBDL-SJU
$110
9/18Wed
1 stopDelta
17h 07mBDL-NAS
$132
5/15Wed
1 stopDelta
8h 19mBDL-SJU
$162

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Last minute flights from Hartford to Caribbean

Last minute flight, train and bus deals

5/14Tue
nonstopFrontier
3h 48mBDL-SJU
5/15Wed
nonstopFrontier
3h 59mSJU-BDL
$197
5/14Tue
nonstopFrontier
3h 48mBDL-SJU
5/17Fri
multi-stopFrontier
15h 36mSJU-BDL
$225
5/13Mon
nonstopFrontier
3h 48mBDL-SJU
5/16Thu
nonstopFrontier
3h 48mSJU-BDL
$231
5/14Tue
nonstopJetBlue
3h 51mBDL-SJU
5/17Fri
nonstopJetBlue
4h 06mSJU-BDL
$252
5/11Sat
nonstopJetBlue
3h 51mBDL-SJU
5/16Thu
nonstopJetBlue
4h 06mSJU-BDL
$292
5/12Sun
multi-stopAmerican Airlines
7h 07mBDL-SJU
5/16Thu
multi-stopAmerican Airlines
7h 05mSJU-BDL
$300
5/12Sun
multi-stopAmerican Airlines
9h 25mBDL-SJU
5/16Thu
multi-stopAmerican Airlines
7h 05mSJU-BDL
$301
5/14Tue
multi-stopDelta
8h 19mBDL-SJU
5/15Wed
multi-stopDelta
8h 41mSJU-BDL
$356
5/14Tue
multi-stopDelta
8h 19mBDL-SJU
5/15Wed
multi-stopDelta
8h 41mSJU-BDL
$361
5/13Mon
multi-stopSpirit Airlines
22h 22mBDL-KIN
5/17Fri
multi-stopSpirit Airlines
23h 47mKIN-BDL
$904

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