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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$326
Santo Domingo
Santo Domingo1 stop$425
Montego Bay
Montego Bay1 stop$354
Oranjestad
Oranjestad1 stop$341
Nassau
Nassau1 stop$326
Kingston
Kingston2 stops$485
Simpson Bay
Simpson Bay1 stop$294
Providenciales
Providenciales1 stop$544
Port of Spain
Port of Spain1 stop$393
Bridgetown
Bridgetown1 stop$453
George Town
George Town1 stop$340
Willemstad
Willemstad1 stop$415
Aguadilla
Aguadilla1 stop$296
Puerto Plata
Puerto Plata1 stop$626
St. John's
St. John's1 stop$697
Punta Cana
Punta Cana1 stop$326
Santo Domingo
Santo Domingo1 stop$425
Montego Bay
Montego Bay1 stop$354
Oranjestad
Oranjestad1 stop$341
Nassau
Nassau1 stop$326
Kingston
Kingston2 stops$485
Simpson Bay
Simpson Bay1 stop$294
Providenciales
Providenciales1 stop$544
Port of Spain
Port of Spain1 stop$393
Bridgetown
Bridgetown1 stop$453
George Town
George Town1 stop$340
Willemstad
Willemstad1 stop$415
Aguadilla
Aguadilla1 stop$296
Puerto Plata
Puerto Plata1 stop$626
St. John's
St. John's1 stop$697
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 $168 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 $168.

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 $337 on average. Morning departures are around 11% 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 $402, 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 $634 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 Sunday 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 2% increase in price.
Most popular time to fly with an average 23% 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 $186 one-way - $297 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.
7.9
SouthwestOverall score based on 4222 reviews
8.6Crew
8.0Comfort
7.0Food
8.1Boarding
7.4Entertainment
Airline reviews

They did not fix the wifi that they knew was an issue on an earlier flight. The flight was filled with business people that were clearly frustrated not being able to work. That can’t happen on a 3 1/2 hour flight. Would rather have been delayed a bit.

6.0 GoodWilliam, Oct 2026
Read more Southwest reviews

They did not fix the wifi that they knew was an issue on an earlier flight. The flight was filled with business people that were clearly frustrated not being able to work. That can’t happen on a 3 1/2 hour flight. Would rather have been delayed a bit.

The WiFi did not work three hours of productivity lost. 15 people from the firm were on the flight. Loss of revenue

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.

Delta is the best. It was all very easy and on time.

The cabin and bathroom experience was poor as the cabin and bathroom were dirty and showed signs of an older plane that had not been updated for Customer’s, comfort and health. There was gum on my seat when I arrived and dirt spots around the fan and light controls. The flight was almost entirely full, so there was no way I could be moved from my seat. Th bathroom had the peeling paint.

Wifi worked inconsistently; outlet to charge computer did not work.

Gate agent in LAS named Juliett should win an award for excellent customer service.

Gate agent and flight attendants were efficient, but more stern than warm.

The only issue is that the plane was HOT. This was not the case on my first flight so not sure why, but thankfully I had a portable fan with me. Everything else was great!

13 hour delay stuck in Detroit and missed a day of meetings. It was terrible

My flight was so delayed I would’ve missed my connection and had to cancel my trip

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.

Return flight was perfect. All on time and no hiccups. However, going was another story. I don't blame United for the weather, but I am rather disappointed in its response to my getting stranded in my layover city for the night. United gave me a $20 food voucher. That's it. But besides this policy, the employees were incredibly helpful rerouting me to my final destination in Fort Lauderdale, FL. So overall, 8 out of 10. 10 out of 10 for flight comfort, inflight service and before flight service. 5 out of 10 for layover handling.

Quinoa chocolate cookies are my favorite! Would be nice to have internet service like American

Better management of the boarding process. Is there any way you could forward all the window seats first? That's the Way Reno Air used to do it, and they had the fastest boarding in the industry!

Old plane, no amenities. Very abrupt landing. Unnecessarily long taxi time.

The flight was for my mom in wheelchair the staff in Newark wer not friendly took a long time to even get a wheelchair she almost missed her flight because they finally got a chair few minutes before boarding they had to rush her to the gate. They took her carryon and checked it as a bag told her don’t worry free of charge but they charge the credit card anyway. She also told me the seats are not comfortable at all as if they were broken she could feel the bars in the seat SFO staff was much better overall she had the worst experience

Wifi is very frustrating - could not connect and therefore unable to work on the trip

Entertainment was great. Seats were good. They did not have my pre-ordered hot food product available but did comp me something cold in place of the item.

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

The crew was friendly and helpful. The entertainment system in my row did not work for movies and TV shows and the Direct TV cut off in parts and stopped showing the baseball playoff game.

Non-stop commercials were frustrating when trying to view direct TV

Forced to check bag, even though plenty of space in overhead bins. Did not appreciate having to wait at baggage claim to retrieve suitcase.

Great. I was in mint class. Security was spectacular. A lot of room on the flight! And the WiFi worked this time- it didn’t work the last time and I am on a business trip so that was a problem.

There was more leg room in what was most likely a basic assigned seat (row 25) then on other airlines I've flown lately.

They lost my luggage and have ruined first day of my vacation. Still don’t have it. I have nothing. I also paid for a seat I did not get. They changed both our seats with no notice. Will never fly this airline again.

My overall experience with JetBlue was pretty poor and disappointing. We originally booked a DIRECT flight home from Boston on 9/28 at 8:00pm even though it cost more than the non direct flights. With no reason other than "unforeseen circumstances", our flight home Monday was cancelled and we were rebooked on a 7:00am flight on 9/29 with a layover in JFK. We were traveling with sick kids coming home from a funeral of a loved one and needed to be at work on Tuesday so paying extra for a flight home Monday was something we had to do. The original direct flights were considerably more expensive than the non direct flights- so I don't understand how Jetblue did absolutely NOTHING to compensate or right their mistake. We will not be booking with them in the future because they are not reliable and they showed no remorse nor did they make any attempt to make things right. The least they could have done was credit the difference in cost of flight because I know our original flights cost more than the one we were rebooked on. Once again- we will not be flying with them in the future and will advise family and friends to be aware of the risk you run when giving them your business. Do better.

The flight attendant was snarky and the flight took off very late. I know it was an issue with air traffic control and the runways in Boston, so not really anyone's fault, but very frustrating, I missed an important meeting because of rgr delay. They didn't offer headphones to watch the TV, but luckily I remembered my own and was able to enjoy watching a movie.

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

The crew in the Vegas airport clearly was having a bad day … they moved on and the crew that checked us in for boarding was great, as was the flight crew. I did get the wheel of my carry on stuck in the overhead bin. Amazing team effort to include the flight attendants, the pilot, and another pilot who was on the flight as a passenger. Finally got it unstuck ✅

Staff are polite,and even offer us to tag our baggages upon seeing us from the entry

Internet is much improved, which is very important to me a s a business traveler. The off boarding of the plane was fantastic. Very quick and very orderly. We had to check our carry-ons before we got on the plane and they were retrieved and available to us very quickly. We left on time and arrived early. All very good things

My seat was defective. The suppor was broken under the cushion so I road on metal for 4 hours

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.

More options for your flight to Caribbean Islands

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