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Cheap Flights from Hartford to Caribbean Islands

Cheapest round-trip prices found by our users on KAYAK in the last 5 days
Punta Cana
Punta Cana1 stop$348
Santo Domingo
Santo Domingo1 stop$417
Montego Bay
Montego Bay1 stop$394
Oranjestad
Oranjestad1 stop$372
Nassau
Nassau2 stops$326
Kingston
Kingston2 stops$491
Simpson Bay
Simpson Bay1 stop$294
Providenciales
Providenciales1 stop$543
Port of Spain
Port of Spain1 stop$393
Bridgetown
Bridgetown1 stop$444
George Town
George Town1 stop$357
Willemstad
Willemstad1 stop$405
Aguadilla
Aguadilla2 stops$306
St. John's
St. John's1 stop$696
Puerto Plata
Puerto Plata1 stop$592
Punta Cana
Punta Cana1 stop$348
Santo Domingo
Santo Domingo1 stop$417
Montego Bay
Montego Bay1 stop$394
Oranjestad
Oranjestad1 stop$372
Nassau
Nassau2 stops$326
Kingston
Kingston2 stops$491
Simpson Bay
Simpson Bay1 stop$294
Providenciales
Providenciales1 stop$543
Port of Spain
Port of Spain1 stop$393
Bridgetown
Bridgetown1 stop$444
George Town
George Town1 stop$357
Willemstad
Willemstad1 stop$405
Aguadilla
Aguadilla2 stops$306
St. John's
St. John's1 stop$696
Puerto Plata
Puerto Plata1 stop$592
Booking Insights

KAYAK's insights & trends for Hartford to Caribbean Islands flights

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

What is the cheapest Hartford to Caribbean Islands flight route?

The cheapest ticket to Caribbean Islands from Hartford found in the last 5 days was to San Juan, at $161 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 $161.

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

The cheapest time of day to fly to Caribbean Islands is generally in the afternoon, when round-trip flights cost $336 on average. Morning departures are around 10% more expensive than evening flights, on average. The most expensive time of day to fly to Caribbean Islands is generally in the morning, which is peak travel time and where the average cost of a ticket is $403.

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

No, with an average price for the route of $392, prices are generally cheapest when you fly direct.

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

The cheapest month for flights from Hartford to Caribbean Islands is March, when tickets cost $481 (return) on average. On the other hand, the most expensive months are December and July, when the average cost of round-trip tickets is $628 and $620 respectively.

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

Your flight ticket price will generally be cheaper if you fly to Caribbean Islands on a Tuesday and more expensive on a Thursday. On your return trip to Hartford, you should consider flying back on a Friday, and avoid Sundays for better deals.

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

To get a below average price on the flight from Hartford to Caribbean Islands, 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
Best time to beat the crowds but there is an average 1% increase in price.
Most popular time to fly with an average 22% increase in price.

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.

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 $174 one-way - $285 round-trip

Reviews of the top 5 airlines serving from Hartford to Caribbean Islands

 
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
SouthwestOverall score based on 4211 reviews
8.0Comfort
8.1Boarding
8.6Crew
7.0Food
7.5Entertainment
Airline reviews

I understand the delays caused by the storm, but that doesn’t mean the systems had to be chaotic. The app showed one thing, the screens showed something else, and the gates kept changing every 10 minutes. It was a nightmare trying to figure out where to go.

2.0 MediocreWatimosin, Oct 2026
Read more Southwest reviews

I understand the delays caused by the storm, but that doesn’t mean the systems had to be chaotic. The app showed one thing, the screens showed something else, and the gates kept changing every 10 minutes. It was a nightmare trying to figure out where to go.

Multiple delays due to weather in Chicago, but the crew did their best to get flights rescheduled and on to their destination. I felt like the crews handled a frustrating situation very well, kudos to them! I was very glad to not have a cancelled flight.

The flight was smooth. The Southwest experience has degraded overall, but this one was okay.

The last 3 flights between BWI and BDL canceled the beverage service mid- way. Just say up front that the fight is too short. Thanks!

It was okay. The plane was delayed from earlier in the day, but they kept updating the departure time, sometimes later, sometimes earlier. That was stressful. Once we finally got on and took off, it was fine. I was supposed to have a connection in Chicago to Los Angeles, and the time for so late I was rebooked to arrive in LA 3 hours late. The departure time to Chicago later became early enough to have taken my original connection and arrive earlier but that wasn't an option.

It was fine. For some reason the flight was much longer than usual. It may have been explained, but I had noise cancelling earbuds on and missed a couple of announcements. The crew was fine, but there was a flight attendant who kept telling dumb jokes, occasionally one I found distasteful. This was my second time with him, but luckily it was a late flight so he didn't do as many. But I heard all of today's jokes twice, which was two times too many. Good takeout and landing.

Boarding good… although I wish SW had another seating system. We had to rush the beverages as the flight was only 50 minutes. It seemed to take forever for my husband to get the wine he ordered, and my coffee. We were then told to drink it like we were in collage, as landing was soon…..

Paid for early bird. Basically paid for nothing. Would have been in the same spot regardless since the entire plane family preboarded between A and B. If they can’t give you A they should be required to refund the early bird fee. Also I don’t know what the issue is with the flight attendants but their attitudes need to change.

Would have liked screens on the back of each seat.

The boarding process of Southwest and the “first come first serve” seat selection is very difficult and prolongs the actual boarding process as people figure out where to sit.

Leslie the gate agent was incredibly helpful with helping me get on an earlier flight! I saved several hours of airport time thanks to her, and she made the process easy and quick.

Two of the flight attendants were cranky and seemed like they didn’t want to be there. Not up to normal Delta standards. And our bags didn’t make flight to Italy from Amsterdam resulting in having to make a trip back to airport which cost me 75 euros.

The trip to Harrisburg from Detroit was extremely uncomfortable because of heat

Flights were on time, my connecting gate was VERY close to my arrival gate, everything went smooth and made for a delightful experience.

The flight was freezing cold. I had on pants and a sweatshirt, had to wrap up in the blanket provided AND put on my rain coat, and was still chilly. Have never been on such a cold plane.

The flight was delayed to board, then delay in landing and extremely bumpy landing.

Late flight, screens not working and still had to pay for a drink

great! appreciated the last minute upgrade to Comfort+ exit row, as well

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.

Please stop those idiotic and unrelenting announcements, commercials and stupid credit card drivel. All together about 15 minutes of stupidness that annoys each passenger.

On time. Carry on and personal bag was accommodated on the plane. Entertainment was accessible without bringing own device. Whole can of juice was provided rather than a pour.

On time. Accommodated carry on and personal bag in the plane. Good entertainment available and access without using own device. Gave a whole can of juice rather than a pour. Seat did not recline much.

Flight attendant incredibly rude. Stuck her finger in my drink and didn’t even have the courtesy to apologize.

I like the first class seat amenities like the phone charger on the armrest even though it didnt really work on mine and the partition between the seats. I also liked that there were additional places to stash things during the flight. The food I got was steak and it was really tough to cut with the knife. Chewy too. A little disappointed in that. I liked that your name is on the screen too. nice touch. great service overall.

Good, our flight was delayed but that was totally out of their control due to weather and a presidential visit.

overall a very good travel experience - left on time, arrived early. Mostly a smooth flight. Polaris seats were excellent, very good service and nice food with options.

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

No WiFi, no power to charge phone, confusing boarding, delays

There is a considerable amount of people that use the wheel chair pre boarding along of large groups of family / friends. This is not right should be limited only to the person in need and the airline assistant. Some of these people use overhead bins that do not belong to them. The aircraft had a non functional wifi . The service was bad.

Flight was delayed 3 hours. No food on plane besides snacks

Every thing went smooth. No complaints except deplaning could have been quicker

I was grossly overcharged to change my return flight. Had to do it through Kayak because it was booked that way and I was not given the fare price listed at the time on JetBlue or kayak. Was traveling with another couple that booked directly through JetBlue and they paid the $100 change fee and the difference between what they paid originally(same as me) and the displayed fares and it was less than $400 total for two tickets. I paid almost $700 to change the same fare tickets they purchased and had to pay again for upgraded seat selection that I previously paid for on top of the almost $700 increase. Difficult to talk to the kayak representative because of his accent. Told me I had to wait for confirmation to be sure it had been changed and that I could take up to a few hours. The call itself after the wait time took almost 30 minutes, which could’ve been done directly on JetBlue in 2 to 3 minutes.. My husband and I were given separate boarding zones. They would not let us board together. I had to board in the last zone. They made me check my bag even though my husband told me that he had a spot to put my carry-on. Since he boarded before me. The flight crew tried to accommodate, but the woman that was boarding in the terminal came down and would not let me take my carry-on. She was aggressive, rude and condescending to everybody in line and told them she was being audited. When I told her that my husband had secured a spot for me to put my carry-on with his backpack, that would then move to under the seat. She told me that she couldn’t play favorites, although I was second to last to board the plane since my boarding zone was changed. They told me because I forwarded my husband his ticket that’s what separated our boarding zones, but would not allow us to board together. The volume on my TV would not work, and my upgraded seat would not go into the fully upright position so I was told repeatedly during takeoff and landing to put my chair into the upright position which was embarrassing and uncomfortable to be told assertively so many times. I will not book through kayak again.

Nice plane, with TV, comfortable seats and leg room. Updated regularly on time changes

Overall, it was a fantastic experience had no movies up charge for everything haven’t flown in many many years. Crew is fantastic. Flight was good overall great experience.

My sons tv wasn’t working and they didn’t give him a kids meal I have to request it prior and no one told me!!! Then the 2nd flight they split us up. My two year old can’t sit alone on the plane hello?????

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

There was no clear update on the flight until last minute and made it an hour delay. No clear flight aircraft or incoming flight which we will be boarding. We would plan accordingly for our connecting flight. This is one one the worst service, I also had to buy an another ticket with different ai carrier. American airline was not letting me plan my trip, made us just waiting. Not a good service at all.

The flight attendance were very pleasant and funny. They made boarding and the flight very pleasant. Just wish the seats cushions had more comfort. Very flat and hard.

Flawless as usual. I understand on the smaller airplanes that WIFI is not available, and that is expected. The crew were awesome!

Our trip to Spain turned into a stressful ordeal with cockpit issues and FAA air traffic disruptions. Our American Airlines flight from Raleigh to JFK was delayed nearly four hours, causing us to miss our connections to Madrid and Jerez. We were left stranded in New York with children, even running out of diapers while trying to sort everything out. American refused to cover hotels or rental cars, leaving us to arrange and pay for them ourselves. The delays also disrupted our prepaid rental car reservations in Spain. It was a frustrating and expensive start to a family trip we had spent months planning.

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.

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