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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$313
Santo Domingo
Santo Domingo1 stop$376
Montego Bay
Montego Bay1 stop$404
Oranjestad
Oranjestad1 stop$342
Nassau
Nassau1 stop$306
Kingston
Kingston1 stop$495
Simpson Bay
Simpson Bay2 stops$290
Providenciales
Providenciales1 stop$514
Port of Spain
Port of Spain2 stops$524
Bridgetown
Bridgetown2 stops$489
George Town
George Town1 stop$398
Willemstad
Willemstad1 stop$451
Aguadilla
Aguadilla1 stop$276
Puerto Plata
Puerto Plata1 stop$666
St. John's
St. John's1 stop$737
Punta Cana
Punta Cana1 stop$313
Santo Domingo
Santo Domingo1 stop$376
Montego Bay
Montego Bay1 stop$404
Oranjestad
Oranjestad1 stop$342
Nassau
Nassau1 stop$306
Kingston
Kingston1 stop$495
Simpson Bay
Simpson Bay2 stops$290
Providenciales
Providenciales1 stop$514
Port of Spain
Port of Spain2 stops$524
Bridgetown
Bridgetown2 stops$489
George Town
George Town1 stop$398
Willemstad
Willemstad1 stop$451
Aguadilla
Aguadilla1 stop$276
Puerto Plata
Puerto Plata1 stop$666
St. John's
St. John's1 stop$737
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 $163 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 $163.

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 8% 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 $405.

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 $660 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
Most popular time to fly with an average 29% 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 $191 one-way - $291 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 4217 reviews
8.1Boarding
8.0Comfort
7.0Food
8.6Crew
7.4Entertainment
Airline reviews

On time departure and arrival. Had to be the oldest plane in the SWA fleet but it got me where I needed to be.

8.0 ExcellentJohn, Oct 2026
Read more Southwest reviews

On time departure and arrival. Had to be the oldest plane in the SWA fleet but it got me where I needed to be.

Flight was delayed out of BWI unexpectedly / without a reason given but otherwise ok.

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.

Love Delta. I'll take connections to stay on Delta even if another airline has a direct flight.

The main issue was the quantity of the drink. The hostess gave only half cup full of the soft drink. I was thirsty and was expecting full glass like every other time.

Delta always provides stellar service. I am always impressed and will try my best to travel via Delta if I can afford it.

Everything was pretty good. I would like to have more drinks (water) during four hours of the flight.

This flight was the flight we missed due to deltas delay at our first airport going TO Atlanta.

Wi-fi was out for the whole flight. I pay a premium to fly Delta because it has wifi and because it was out I didn’t get to work on anything I wanted to. I’ll have to make it up later this week by spending less time with my family.

I enjoyed the whole flight and the crew was amazing i dont usually fly delta

Very nice the whole crew was amazing and very professional. I had an offer for a drink it was handled great and amazing crew and nice flight.

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 need to note that this flight experience was generally fine but the boarding situation was absolutely a mess and there wasn’t any actual priority boarding. I rated the experience poorly because I’m am genuinely so frustrated with the crew on United taking the baggage space in first class. This flight it didn’t happen, but the last few flights (when I ironically don’t get an opportunity to provide feedback) have been spoiled because upon entering the first class cabin as one of the first few seated passengers, the overhead bins are full and ‘crew’’ tags are on the bags of those taking space. I don’t intend to infer some sort of a class or caste system but it’s absolutely ridiculous that the crew takes the overhead storage above and beyond their most loyal and lucrative customers. They should not even have economy space IMO. And I’ve gotten grief when I’ve noted to the crew the ridiculousness of the notion that the crew (who are the last off the plane) should have priority over flyers who pay. I hope you find a way to convey this message to United because it’s happening with increasing frequency and I intend to find a way to expose the specific crew members who are doing this on a flight by flight basis. (And I have a day job)

Great flight and crew. Need more legroom and DO NOT allow seats to recline.

Flight and crew were great. Need more legroom and do not allow seats to recline.

Bathrooms broken, Wifi not working, Direct TV stuck in a United credit card loop for whole flight

We arrived to Chicago nearly 30 minutes early, which was great, but then was on the ground for over an hour because the gate was not available. The issue I had was the pilot estimation was frustrating. First he said he was informed it would be 20 minutes but he said "it will probably be more like 10 minutes". After 30 minutes he came back on the comm and said it would be another 10 minutes, maybe 20. I understand he was only giving estimates but he also layered in his own gut feel. We were never told why we didn't have a gate even after our scheduled entry.

Just sat on the run way after we arrived early

New Max 10, first class seats have been shrunk. End of a 20 hour journey, it was United not Lufthansa, just glad to get home

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 boarding agent and checked bag agent were both rude. It only takes a second to be kind. However, the flight crew was amazing. I got a turkey sandwich and it wasn't bad---not great but not bad. The internet was my biggest problem. This was a work trip and I REALLY needed the internet to meet a deadline but it didn't work for 80% of the trip. Very disappointing.

I tried to check in beforehand from Ireland. The Jet Blue website sent me to the Aer Lingus website and vice versa. I tried to get a boarding pass at Dublin Airport as well, but they said they couldn't help me either. I had to wait until I arrived at the gate in Boston to secure a boarding pass...it was a bit nerve wracking.

Great flight. Best in years. Very clean craft. Easy boarding. Communicative pilot. Friendly flight attendants. Absolutely smooth take off, in flight and landing. Very comfortable seats. Smoothest flight I've experienced in years. THANK YOU JET BLUE!

I was asked to pony up an additional $239 (over the $735 paid originally) for a one way middle seat, which was very uncomfortable. Where did you expect me to sit?

Jet Blue sevice was good. Just don't understand why they charge for earphones to listen to flight entertainment. Other than that, everything was excellent.

Mostly good, flight take off in time and land earlier I can’t ask for more..

The crew was not nice this time. I asked for a drink one time and the girl didn’t say anything to me and just got me the hot drink while walking super fast to the back. We were sitting in the back and she wasn’t doing anything except socializing. She was upset I asked for something and she had to do her job. I also didn’t fully have it in my hands when she handed it to me so it was dangerous. She was abrupt and rude. She wouldn’t allow for people to spread out like previous flights we had been on if they were empty, and there were empty rows. It was strange and she enjoyed being angry at us.

The plane was FREEZING COLD. Like I was wishing I'd brought gloves. Is this how JetBlue sells more blankets? Other than that, all fine. Crew just as nice as usual. A flight attendant asked (who? The pilot?) to have the air turned down for a great number of passengers who were as cold as I was. They (again -- who is "they") did not.

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

Cabin staff were very disengaged, spoke with no eye contact, dismissive. Disappointing compared to my United experiences.

awful delay, awful communication, zero updates throughout the experience of a giant delay

It was decent, there was no WiFi on the flight but the FA’s gave everyone a warning once we boarded the plane. Unfortunately it didn't give me enough time to download my entertainment content.

The crew were diligent about ensuring that our pet dog remained in his carrier for the entire flight, as is their mandate. I wish that mandate was changed so that our poor, scared pets can be comforted during a flight, whereas service animals get to stay out and about for the whole flight. Thank you.

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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