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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$413
Santo Domingo
Santo Domingo1 stop$431
Montego Bay
Montego Bay1 stop$348
Oranjestad
Oranjestad2 stops$342
Nassau
Nassau1 stop$318
Kingston
Kingston1 stop$531
Simpson Bay
Simpson Bay1 stop$305
Providenciales
Providenciales1 stop$524
Port of Spain
Port of Spain1 stop$413
Bridgetown
Bridgetown1 stop$469
George Town
George Town1 stop$378
Willemstad
Willemstad1 stop$431
Aguadilla
Aguadilla1 stop$260
Puerto Plata
Puerto Plata1 stop$626
St. John's
St. John's1 stop$702
Punta Cana
Punta Cana1 stop$413
Santo Domingo
Santo Domingo1 stop$431
Montego Bay
Montego Bay1 stop$348
Oranjestad
Oranjestad2 stops$342
Nassau
Nassau1 stop$318
Kingston
Kingston1 stop$531
Simpson Bay
Simpson Bay1 stop$305
Providenciales
Providenciales1 stop$524
Port of Spain
Port of Spain1 stop$413
Bridgetown
Bridgetown1 stop$469
George Town
George Town1 stop$378
Willemstad
Willemstad1 stop$431
Aguadilla
Aguadilla1 stop$260
Puerto Plata
Puerto Plata1 stop$626
St. John's
St. John's1 stop$702
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 $166 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 $166.

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 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 $404.

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

No, with an average price for the route of $412, 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 $639 and $619 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 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 $189 one-way - $304 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 4215 reviews
7.5Entertainment
8.0Comfort
8.6Crew
7.0Food
8.1Boarding
Airline reviews

Flight boarded 2.5 hours late (my second southwest flight of the day with late departure), the gate agent was grumpy and unhelpful. Said she was "tired so we aren't going to follow normal boarding order". No complaints about the actual flight crew.

2.0 MediocreBrittney, Oct 2026
Read more Southwest reviews

Flight boarded 2.5 hours late (my second southwest flight of the day with late departure), the gate agent was grumpy and unhelpful. Said she was "tired so we aren't going to follow normal boarding order". No complaints about the actual flight crew.

Your computers were down and took a long time to check baggage

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.

My bag was open when I got to Portland and all my clothes were wet and my parking pass was wet

Had to deplane 2 x due to problems with plane. Delayed over 6 hours ans was given a $12 food credit which barely oaud for anything and limited to wear incoukd redeem.

After boarding the plane had to wait an hour at the for the copilot to show up before we could depart

No beverage/snack service without any explanation or reason. Late boarding and delayed flight.

more room in seats, larger snacks, more comms with delays

There was overbooking that delayed boarding. Then an airport emergency lockdown that caused further delays in boarding. However the time was made up during flight and there was a minimal delay in landing. Everything else was excellent.

Very crowded and the economy seats were the smallest and with the least legroom I have ever experienced. Cabin staff were excellent although the food service was chaotic as they were being each person their food individually instead of from the wagon.

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

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.

I especially enjoyed having a lightly packed flight which enabled me and my wife to occupy a three seat area with nobody in the middle seat.

Fantastic experience once again flying with United! There was great communication from the cockpit and one of the flight attendants went out of her way to get my two little kids some special treats which elevated our travel experience coming home.

1) United economy seats barely recline. 2) I have yet to get United WiFi to work, after numerous flights.

Flight attendants need to know their plane. Seated in first row yesterday. The seat had about a 1 inch recline that was not adjustable. I don't appreciate being awakened to raise a seat that can't go any further forward and such a small recline is either irrelevant or the plane needs to be repaired. Not the way to treat any customer and especially the ones who have paid that level of money for the seats.

The experience was good overall; however, my United Airlines Mileage Plus Account didn't reflect my flights to Houston from Newark. In essence, my mileage rewards points do not reflect my actual travel. This should be corrected.

Delayed - leaving, delayed getting to the gate at destination. What should have been a very easy flight and experience was not.

Plane arrived an hour before departure. Plane was completely boarded and ready for push back when they decided they needed to change a tire. 1 hour delay on the plane when this could have been done before we got on the plane.

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

Unacceptable pre-boarding ticket issues. Paid for and reserved Mint seat approximately a month in advance. Checked in to flight in Mint seat 24 hours before flight. Shortly before flight, was bumped out of Mint entirely, even though other Mint seats were still available and for sale. Was told it was "operational", however seats were still available/being sold. Got to gate and they could not explain it, but the gate agent was able to put me back into Mint (however to a different seat). Nothing proactive done by Jetblue, I would have been bumped had I not arrived at gate early enough to have a helpful gate agent rectify. No explanations from Jetblue.

The crew did not ensure the Evermore seats had their carry on space available. When my family and I boarded, we saw people putting their carry on suitcases in the overhead spaces above our seats and then proceed to the rear part of the plane. This resulted in us having to check our bags and being late to our meetings/events.

Crew was friendly. Free headphones would be nice. Free new movies would be better.

Diana at the gate was unhelpful which was fine, but she was also rude which I did not appreciate at all.

Multiple delays, poor communication, dismissive staff, chaotic boarding, broken seat back entertainment. Not really much to like.

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.

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

We did not fly on American Airlines from Chicago to London. We were rebooked on British Airways (by American Airlines) and our luggage was left behind. A full day delay and lost luggage.

Business class flight attendant was very good. But our flight was delayed two hours for a “mechanical” bathroom issue that literally took 5 minutes to fix. Our plane landed early from its previous flight but still waited for a mechanic to show up to fix an obvious minor issue for almost three hours. This caused us to miss our connecting flight. They put us up in a Days Inn that was 17 miles away from the airport that took a half hour of driving just to get to and this was at 11pm at night. Then when we finally got back on a plane after a full day delay they left our luggage back in the airport. This was an international flight, so no luggage or belongings after flying 8 hours to a different country. We will NEVER fly American Airlines again.

12 hour wait in pdx to my initial flight to Dallas to hunstville

I was able to enlist on standby for an earlier flight, and eventually made it (last row). However, the experience was poor and felt unfair. On the standby list, I was ranked #2 (#1 had been cleared a seat). The person ranked as #3, who was also in the queue alongside me was given a seat much earlier - with group 4 boarding (a seat within the first 2 rows after business class). When inquired about why I was skipped-over on the priority list, the gate agent first paused (likely cuz she couldn't explain) - and then gave me the standard expectation that if a space opens up, she'll give me the seat. Despite my priority ranking being higher, I was unduly held-back, and could have missed the plane - unfairly giving advantage to someone else. Luckily one seat opened up; but given the unfair assignment of standby seat by gate-agent, this was a subpar boarding experience.

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

Complete your trip to Caribbean Islands with a hotel stay or car rental