$54 Find Cheap Flights from Hartford to Caribbean Islands

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 Islands departing on 2/22. 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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These are the airlines KAYAK users have selected most often from within our search results in flight searches from Hartford to Caribbean Islands.
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Hartford to Caribbean Islands.
In the last 7 days travelers have searched 41,299,237 times on KAYAK, and here is why:

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Best Caribbean Islands Flight Deals from Hartford

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

Punta Cana
Punta Cana1 stop$210
Santo Domingo
Santo Domingo1 stop$249
Montego Bay
Montego Baynonstop$268
Oranjestad
Oranjestad1 stop$373
Nassau
Nassau1 stop$381
Simpson Bay
Simpson Bay1 stop$219
Kingston
Kingston1 stop$331
Providenciales
Providenciales1 stop$356
Bridgetown
Bridgetown2 stops$508
Port of Spain
Port of Spain2 stops$641
George Town
George Town1 stop$426
Willemstad
Willemstad1 stop$520
St. John's
St. John's1 stop$637
Puerto Plata
Puerto Plata1 stop$445
Aguadilla
Aguadilla1 stop$220

Good to know

Low season

September

High season

April

Cheapest flight

$54
Best time to beat the crowds with an average 22% drop in price.
Most popular time to fly and prices are also 0% lower on average.
Flight from Hartford to San Juan Airport

FAQs - booking Caribbean Islands flights

  • How does KAYAK find such low prices on flights from Hartford to Caribbean Islands?

    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 Islands.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Hartford to Caribbean Islands?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Hartford to Caribbean Islands 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 Islands?

    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 Islands 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 Islands?

    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 Islands 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 Islands

  • 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 - $227 round-trip
  • Book at least 1 week before departure in order to get a below-average price.
  • High season is considered to be June and July. The cheapest month to fly from Hartford is September.

Top 5 airlines serving from Hartford to Caribbean Islands

 
See real verified KAYAK customer reviews for airlines flying from Hartford to Caribbean Islands. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Hartford to Caribbean Islands? 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 8501 reviews
8.0Comfort
8.2Boarding
8.6Crew
7.3Food
7.9Entertainment
Airline reviews

Seats were really tight and the seat belts did not give enough slack.

8.0 ExcellentElizabeth, Jan 2025LGA - RIC
Read more Delta reviews

Seats were really tight and the seat belts did not give enough slack.

I like in St George and prefer to fly out of CDC than SGU. Hopefully, they will continue the flights out of Cedar

Broken jer bridge. Poor communication about it. Lost 2 of 4 luggage pieces

Overall, it was okay. Seat was a little cramped. Would’ve liked more substantial snacks or opportunity to buy some.

Newer plane, relatively easy boarding, not a full flight and was told that we could not be moved up because of weight and balance issues. Otherwise, a very good experience.

Other then mechanical/ computer problem and 3.5 hours flight delay the flight was great. I guess that what happened when you fly an old airplane now a day.

I was with one of the last zones to board. It was kind of annoying to finally get called to board and my whole section was already on the plane. Clearly they boarded with previous zones. So by the time I got on board, there were no spaces for my luggage above my head. I had to put my luggage 4+ rows behind me, which meant that I had to wait even longer to get off the plane, since I had to wait for those rows to clear the aisle before I could retrieve my luggage and exit the plane. This also held up the plane cleaners, as they couldn't service my row until I cleared it, so they were all standing there waiting for me, while I'm standing there waiting for the other passengers to clear the aisle. Anyways, I wasn't in a rush this time, so I just waited, but I could see that being a problem in the future. Now, I could have checked my luggage, of course, but coincidentally, a friend of mine on the same flight got their luggage damaged (wheel completely knocked off) and was told by the Baggage Attendant in the airport that Delta doesn't "cover wheel damage" on luggage. This was disappointing to hear. I'm glad I didn't check mine through. If it were my luggage, I'd be highly frustrated to hear that. It makes me not want to check my luggage in the future.

The dear was very limited in space. I could put my water bottle in seat basket. Also, there was no inflight entertainment in the delta app?

Typically I give delta excellent reviews. Our flight was delayed 2hrs, I was one of the fortunate ones who were able to get to my connecting flight. Also, annoying that on the connecting flight boarding personnel make me put away a small bag into my carryon. It small enough to put in back pocket seat, why hold me and the line up to just push it into my carryon.

Logan airport construction meant that boarding was chaotic crowded and delayed

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

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

Very well organized both boarding and deplaning. Very satisfied with the service I received.

I rate it is good we had a 4-hour travel delay at one point but JetBlue gave out food vouchers and travel points credits for another flight so they try to make up for it

Smooth boarding and friendly crew. Unfortunately as soon as we boarded the unit that provides air circulation failed. The pilot informed us and requested maintenance technicians to check it out. The plane became uncomfortably warm without any fresh air coming in. Plus the repair delayed our departure. I am glad the maintenance crew were able to fix the problem. I also was without use of my tv monitor for the first 1/3rd of the trip.

Flight was on time arrived at the destination 10min early they kept in touch via email

Communication with the customer and stay is important. Staff off with a minor inconvenience but it worked out of course. Also this was a very old Mint Class plane. They snuck this one in on us. The updated aircraft are much better.

The flight itself was fine, but the boarding process was extremely frustrating. There is no one scanning boarding passes - passengers just scan themselves and enter the jetway. By the time my husband and I got on the plane and were halfway to our seats they determined there were too many bags on the plane and everything at that point needed to be checked. This created a lot of unnecessary chaos. They should have alerted people before getting on the plane that they would need to start checking bags instead of waiting until people were already on the plane.

The best flight I’ve had in a while. The plane was like 25% capacity, if that. Smoothest boarding and deplaning process I’ve ever experienced. Wish all flights were this smooth.

Did not enjoy this flight at all. All of my coworkers flew delta and I chose JetBlue because I really value how simple the WiFi and entertainment is and this flight I didn’t get either. Crew staff was unsympathetic to my system not working, everyone I asked for help with was extremely bothered by my request for help.

Oh my gosh, I loved my experience with United! they made me want to travel more often.

Fight was delayed an hour due to operational issues ,then further delayed due to ground control for a total of about 1.30 hours. Salad was completely frozen and flatware was so cold you could barely handle it. Crew was friendly and professional and the flight was smooth. The aircraft was clean and well-serviced.

The flight attendants in First Class were mediocre at best. They did not take our tray away until we were about to land and only did so when I press the call button. The United person at the United Club was asked to get us our boarding pass since we missed the flight due in Chicago. She argued that we did not have seats on the flight given to us in Moline. Furthermore, she was adamant that we did not have a First Class ticket. After I spent much time with her trying to show we were correct, she reluctantly agreed. She was probably the most incompetent ticketing person I have ever met and I have traveled 3 million miles on United plus many additional miles with other carriers. United has definitely deteriorated in more than on way.

The plane was in Moline all night. Consequently, we assumed an on time departure at 8:15am. Unfortunately, and as is the normal case with United in Moline, we departed 2.5 hours late. When the crew came, it was discovered that there was very little heat in the plane. Seems this should have been checked hours before the crew arrived. Then when we boarded and the plane was to be de-iced, the United de-icing truck was not working! We awaited the American Airlines truck. All of this caused us to miss our connection in Chicago. My suggestion is never take United Airlines flight from Moline. We have been disappointed 80% of the time and have vowed to not take United again from Moline.

Flight was delayed two hours. No snacks and no tv screens. My bag got stuck in Chicago

Smooth flight. As always dinner could have been more generous. Breakfast was great.

AWFUL. I have had the experience of traveling with many airlines across the world, and hands down United Airlines is the worst. Not one flight was on time, and I don’t think I met one crew member or staff member who wasn’t rude.

Awful. Worst airline I have ever been on. Crew were among the rudest people I have ever dealt with. United staff members were rude and disrespectful. My flight was delayed, causing me to miss a connecting flight. I understand things happen, but when staff start lying about what actually happened, that is when I have an issue. Just be honest, really it isn’t that hard. I’m being very honest with this review and I don’t find this difficult what so ever. In fact, because of United Airlines, my Christmas holiday was off to a really rocky start. As someone who has traveled across the world, it has only been United that I have had a truly awful experience.

In general ok, my only issue is that they had no hot items for purchase. I had very little time in my connection due to baggage/customs/TSA, thag I barely even had a chance for a stop at the washroom and buy water, to make it to my gate when they started boarding. I had nothing to eat because the trip started early, so I was ready to purchase, and they had nothing except for dry items like snacks. I had to purchase a mediocre, overpriced cheese and fruit board, instead of at least a pizza or sliders that I was planning on getting. Other than that, it was fine. But that’s typical Air Canada, to not have enough.

I completely missed my flight because the first leg was longer than planned. I had to sleep overnight in the airport because no accommodation was provided and then sent to Trinidad in the morning with an anticipated 7 hour layover before my flight to Georgetown which was now with Caribbean Airlines. I tried twice with customer service to see if they could put me on an earlier flight which had seats available but was told it wasn’t possible.

We boarded after several delays due to mechanical failure and a gate change. The seat cushion in the exit row was very compressed and offered no cushion, making the four-hour journey reasonably uncomfortable. The WiFi worked for a few people, but for most, it did not, and you cannot get entertainment unless you can connect—American Airlines flights do not have seatback screens, and you must use your mobile phone.

Terrible. Internet/kiosk glitch prevented baggage checkin. Line at ticket co in Ter was under serviced and did not move. Agents did not call for flight but rather allowed time to pass. Then told each person as they reached the front if line that it was too late to check bags so they’d have to rebook flights. At least 15 people missed the flight as a result of this incompetence.

After several delays and being rebooked onto a layer flight, I had to speak to three AA agents for baggage claim to get an attendant. All were in foul mode and reluctant to assist or offer any assistance.

Only thing that I liked it that I got to my destination safely, otherwise American Airlines stinks.

Improvements in communication and empathy are absolutely necessary for American Airlines staff (top down). It’s like they are numb to the needs of their customers.

You were more on time than United. I'm so over united delays.

Good communication at the gate and very nice crew in the flight

Timely boarding process, made up for lost time even after a lengthy wait for de-icing

My seat was wonky...hard and not much padding. I sat next to the Jumpseat for the flight attendant. Thoroughly enjoyed not have a third seat in that row! Flight attendants were amazing. I couldn't answer the "food quality" question as there is no food served on my short flight. I commend the pilot as I know it was super gusty when we landed. Thanks

Seating was horrible. Small seats. Access to flight information and extras very iser unfriendly. Kept losing internet after paying for it. Staff in madison was as unprofessional and unhelpful.

Better service, stop treating people like cattle, have REAL FOOD for the price of the ticket. YOU ARE IN BANKRUPTCY, WAKE UP!!! ... DO BETTER, PLAN BETTER, GIVE COMFORT AND CARE TO PASSENGERS ... EARN RESPECT AND ADMIRATION, YOU'LL BE REWARDED BY THE PUBLIC.

It was good. All snacks/ drinks must be paid during flight. Bring cash with you.

The plane had to wait an hour before docking, then another 1.5 hrs to get our luggage. Bad experience.

The ticket agent wouldn't check our bags, eventhough the flight was delayed and wouldn't board for another hour. The gate agents were only mildly better than the ticket agent. They also had a terrible attitude and work ethics.

The check-in process at Spirit was horrible. There was no one directing the hundreds of people trying to check-in and drop bags at Spirit. We got in multiple lines and were later told it wasn’t a line. The check-in process needs to be improved. The flight and crew were great.

The flight itself was good. Definitely a no frills flight. Pay for what on flight, drink, snack. Flight was delayed to start with, then after boarding and doors closed, still sat there for another 40mins before backing out for departure. When heading back home, there were 2 delays that put me back home 2hrs later than expected. Both times I had people waiting.

we are al people and we go through stuff so my scale is only how i felt, I understand we are all humans, i would definitely ride with soirit again, people in orlando are very helpful which makes it all the better .

I couldn't understand the crew when they announced it was a new plane and there was therefore no wifi, huh? Seriously lame for 2025!

My experience was very nice. However, my Spirit flight 409 from Las Vegas to Tampa… the gate Associate Tissa was extremely unprofessional and boarder line rude. While in line I found out that my Uncle died… in that moment Tisza asked if I would help in car of an emergency as I paid for an exit row seat. I stayed “I will”… Tissa didn’t hear then implied that I didn’t understand English, yelled that I needed to speak up and other things. Associates like that will cause Spirit airlines to lose customers.

It wasn’t a bad flight just very uncomfortable seating wise.

Book cheap flights from Hartford to Caribbean Islands

Recent round-trip flight deals

 
These are the cheapest round-trip flights from Hartford to Caribbean Islands found on KAYAK in the last 72 hours.
2/22Sat
1 stopFrontier
27h 46mBDL-SJU
2/26Wed
1 stopFrontier
15h 41mSJU-BDL
$106
2/8Sat
nonstopFrontier
3h 50mBDL-SJU
2/15Sat
1 stopFrontier
13h 05mSJU-BDL
$107
1/22Wed
1 stopUnited Airlines
6h 32mBDL-SJU
1/24Fri
2 stopsUnited Airlines
13h 02mSJU-BDL
$227
3/1Sat
nonstopJetBlue
3h 46mBDL-SJU
3/3Mon
nonstopJetBlue
4h 10mSJU-BDL
$238
2/5Wed
1 stopAmerican Airlines
10h 36mBDL-SJU
2/6Thu
1 stopAmerican Airlines
6h 46mSJU-BDL
$242
2/5Wed
2 stopsAmerican Airlines
10h 47mBDL-SJU
2/12Wed
2 stopsAmerican Airlines
11h 45mSJU-BDL
$247
2/26Wed
1 stopJetBlue
7h 54mBDL-SJU
3/18Tue
nonstopJetBlue
4h 10mSJU-BDL
$252
2/9Sun
1 stopUnited Airlines
6h 17mBDL-SJU
2/12Wed
2 stopsUnited Airlines
13h 00mSJU-BDL
$263
3/18Tue
1 stopDelta
7h 10mBDL-AUA
3/25Tue
1 stopDelta
8h 36mAUA-BDL
$377
2/1Sat
1 stopDelta
9h 56mBDL-NAS
2/5Wed
1 stopDelta
8h 12mNAS-BDL
$381

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Recent one-way flight deals

 
Only flying one-way? Below are some of the best one-way flight deals from Hartford to Caribbean Islands found on KAYAK in the last 72 hours.
2/22Sat
1 stopFrontier
12h 33mBDL-SJU
$54
2/25Tue
nonstopFrontier
3h 50mBDL-SJU
$55
2/4Tue
2 stopsUnited Airlines
14h 28mBDL-SJU
$114
2/10Mon
nonstopJetBlue
3h 46mBDL-SJU
$119
1/14Tue
1 stopAmerican Airlines
13h 44mBDL-SJU
$124
1/29Wed
2 stopsAmerican Airlines
10h 42mBDL-SJU
$126
1/27Mon
1 stopJetBlue
9h 41mBDL-SJU
$133
2/9Sun
2 stopsUnited Airlines
14h 28mBDL-SJU
$159
1/27Mon
1 stopDelta
8h 15mBDL-AUA
$213
4/11Fri
1 stopDelta
7h 02mBDL-MBJ
$233

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Last minute flights from Hartford to Caribbean Islands

Last minute flight, train and bus deals

 
These last-minute flight deals are the cheapest flights found on KAYAK in the last 72 hours for flights from Hartford to Caribbean Islands that are departing in the next 10 days.
1/13Mon
nonstopFrontier
3h 58mBDL-SJU
1/25Sat
multi-stopFrontier
13h 40mSJU-BDL
$159
1/13Mon
nonstopFrontier
3h 58mBDL-SJU
1/25Sat
multi-stopFrontier
13h 40mSJU-BDL
$160
1/14Tue
multi-stopUnited Airlines
14h 23mBDL-SJU
1/14Tue
multi-stopUnited Airlines
13h 02mSJU-BDL
$222
1/14Tue
multi-stopUnited Airlines
6h 32mBDL-SJU
1/14Tue
multi-stopUnited Airlines
13h 02mSJU-BDL
$239
1/14Tue
multi-stopAmerican Airlines
10h 36mBDL-SJU
1/15Wed
multi-stopAmerican Airlines
17h 13mSJU-BDL
$242
1/13Mon
multi-stopAmerican Airlines
8h 50mBDL-SJU
1/25Sat
multi-stopAmerican Airlines
6h 46mSJU-BDL
$247
1/13Mon
nonstopJetBlue
3h 46mBDL-SJU
1/22Wed
multi-stopJetBlue
9h 31mSJU-BDL
$257
1/14Tue
multi-stopJetBlue
9h 41mBDL-SJU
1/24Fri
nonstopJetBlue
4h 04mSJU-BDL
$268
1/14Tue
multi-stopDelta
7h 31mBDL-SJU
1/18Sat
multi-stopDelta
10h 23mSJU-BDL
$325
1/11Sat
multi-stopDelta
8h 17mBDL-SJU
1/17Fri
multi-stopDelta
8h 40mSJU-BDL
$382

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Everything you need to know for your flight to Caribbean Islands

Information on your arrival and departure airports

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