$108 Find Cheap Flights from Hartford to Caribbean Islands - Compare and Save

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 8/31. 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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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$363
Santo Domingo
Santo Domingo1 stop$340
Montego Bay
Montego Bay1 stop$337
Oranjestad
Oranjestad2 stops$407
Nassau
Nassau1 stop$324
Kingston
Kingston1 stop$456
Simpson Bay
Simpson Bay2 stops$347
Providenciales
Providenciales1 stop$543
Port of Spain
Port of Spain1 stop$359
Bridgetown
Bridgetown1 stop$424
George Town
George Town1 stop$357
Willemstad
Willemstad2 stops$375
Aguadilla
Aguadilla1 stop$302
St. John's
St. John's1 stop$582
Puerto Plata
Puerto Plata1 stop$576
Punta Cana
Punta Cana1 stop$363
Santo Domingo
Santo Domingo1 stop$340
Montego Bay
Montego Bay1 stop$337
Oranjestad
Oranjestad2 stops$407
Nassau
Nassau1 stop$324
Kingston
Kingston1 stop$456
Simpson Bay
Simpson Bay2 stops$347
Providenciales
Providenciales1 stop$543
Port of Spain
Port of Spain1 stop$359
Bridgetown
Bridgetown1 stop$424
George Town
George Town1 stop$357
Willemstad
Willemstad2 stops$375
Aguadilla
Aguadilla1 stop$302
St. John's
St. John's1 stop$582
Puerto Plata
Puerto Plata1 stop$576
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?

Data is based on round-trip flight searches on KAYAK over the past month.

The cheapest ticket to Caribbean Islands from Hartford found in the last 5 days was to San Juan, at $169 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 $169.

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

The average price for all round-trip flights from Hartford to Caribbean Islands depending on the time of departure, clicked by users on KAYAK in the last 2 weeks.

The cheapest time of day to fly to Caribbean Islands is generally in the afternoon, when round-trip flights cost $338 on average. Morning departures are around 13% 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?

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

No, with an average price for the route of $384, prices are generally cheapest when you fly direct.

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

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Hartford to Caribbean Islands, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Hartford to Caribbean Islands is January, when tickets cost $479 (return) on average. On the other hand, the most expensive months are July and June, when the average cost of round-trip tickets is $626 and $614 respectively.

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

The average price of all round-trip flights from Hartford to Caribbean Islands clicked on KAYAK for each day over the last 12 months.

Your flight ticket price will generally be cheaper if you fly to Caribbean Islands on a Tuesday and more expensive on a Friday. 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 calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from Hartford to Caribbean Islands, removes the top 0.1% to account for outliers, and then takes the average of all the values for each week.

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

Cheapest flight

$108
Best time to beat the crowds with an average 10% drop in price.
Most popular time to fly with an average 22% increase in price.
Flight from Hartford to Nassau

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 $167 one-way - $290 round-trip

Reviews of the 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
SouthwestOverall score based on 4218 reviews
8.0Comfort
7.0Food
7.5Entertainment
8.6Crew
8.1Boarding
Airline reviews

Flight left on time and was early landing. Seats not comfortable and not enough space…

4.0 OkayLeo, Aug 2026
Read more Southwest reviews

Flight left on time and was early landing. Seats not comfortable and not enough space…

Flight left on time. Seat spacing is way too small…

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.

an he late. super rude gate agent, to every person. spoke down at people.

One of the restrooms didn’t work. The ones that did never got replenished. Flight attendant just sitting there on their phone. No notification that the bathroom was broken so long lines. Apathetic crew.

Pushing back flight and ultimately cancelling it after multiple changes and hours of delays. Comm were terrible as to what was going on and what options were available.

Even though we arrived early and checked in, for some unexplained reason, our bags were removed from the plane and put on the next flight. It took over 12 hours after arriving to get our bags.

Stewardess was not accommodating when I requested a second drink.

The morning calzone was less than impressive and we ended up with heartburn

Some of the passengers are coming on board with luggage so overstuffed and/or too large that have no business going into the overhead bins.

I am in a wheelchair The gate agent knew exactly how to boarding A wheelchair first also the flight attendant knew exactly what she was doing

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.

This flight has a history of leaving late, however, I was pleasantly surprised that it was not delayed this day. The flight went smooth, except I was in a window seat and the wall and my feet were freezing. I found it difficult to sleep due to being so cold, I also was using 2 provided UAL blankets and could not get my feet warm. This was annoying, but I still made it there on time and safe.

Staff didn't seem confident about the ingredients in my lactose intolerance meal

the seat has a problem. the back had a hole.

The back to back mechanical delays from Denver to San Diego and then on my return flight from Denver to Great Falls it added extra time both ways

Really old place. Not as clean as it should be, tray tables needed better cleaning. The items, trays and some other items need to b6 engineered. Anything task you or crew may do is incredibly load, seriously engineer for quiet smooth, easy. Just opening and closing the tray table is actually dangerous and can easily injure a finger. I'm sure it happens as it happened to me! First time I used United and likely will be the last!

Like the fact that the boarding was expedited. But the delay and chaos around the onboarding was not appreciated.

Flight was 2.5 late. Maybe not United’s fault but late none the less. We were late as well on the first leg. WiFi quit working with an hour left.

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

Flying on this airline is nothing short of a full blown circus clown show. On a recent return from my mother’s funeral, my only available choice from IND to PWM was American, which I hesitantly booked as I rarely fly them for many of the following reasons and never will again. I was booked IND-PHL-PWM totaling about six hours. The flight was cancelled due to NE weather. They rebooked me on a two stop flight IND-DFW (Yes DALLAS)-PHL-PWM, still all on the same day. After arriving in DFW, they continually delayed the DFW-PHL flight due to maintenance issues on the arriving flight. Finally it was delayed to the point that my PHL-PWM connection was no longer possible. They then rebooked me thru LGA with the short flight the NEXT DAY to PWM and offered to put me up for the night in NYC (or so I assumed). The flight DFW-LGA was then delayed so much that I asked to be put in an earlier flight with a lessor delay. Throughout this day chats with their AI assistant were useless as were subsequent chats supposedly with a real person(?). Only one customer service agent in DFW was actually helpful and appeared to care. Upon arrival at LGA post midnight, they issued me car and hotel vouchers in Trenton NEW JERSEY at a very old Howard Johnsons ONE HALF HOUR from LGA. The hotel was an $85, 1.5 rated hotel in a very sketchy area of NJ that I would have never voluntarily booked. As I prepared to catch the car back to LGA the next morning I received a text that my flight was cancelled. TWICE IN TWO DAYS. I went to LGA hoping to have AA book me on an earlier Delta flight. The full service line was at least 200 people deep, so I tried to reach a real person agent by phone. After 1/2 hours on hold I gave up and waited for my later LGA-PWM flight. It actually started boarding on-time, but only shortly after announced a maintenance hold. We were told it was nothing serious, just an adjustment to the Captains seat. Only one update was given while we waited 1.5+ hours for a “SEAT ADJUSTMENT”. Can’t forget to mention that on all of these planes the WiFi only worked on two. During that time at least three others flights in my area announced that they were overbooked and were taking volunteers before bumping people. Another flight to ORD announced a gate change and less than five minutes after announced that they were really not changing and announced for everyone to return to that gate. Can’t forget to mention that on all of these planes the WiFi only worked on two.🤡🤡

Paid for wifi but it didn't work once. Seats were incredibly cramped and passengers sitting in front was reclined the entire time and staff did nothing

Delays and cancellations. Mechanics weren’t on site. Replacement plane took hours to arrive although it should have arrived within 90 minutes. Flight back was cancelled. Ended up driving over 12 hours and wasting 3 days between everything.

Flight was delayed multiple times and rerouted to different concourses in the airport because of all of American's delays. App/boarding pass would not update with changed gate information.

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.

It was my first time in Jetblue flight in 10+ years(?) and the experience was horrible. You were better before. There were ATC delays sitting/waiting in the tarmac for 2 hours, I understand that this isn't Jetblue's problem but how the matter was handled poorly is. Cabin was so warm and hot couldn't get it to cool down for the entire waiting period worse, even during cruise flight. Start, the passengers were spoken to and treated like a little children with no respect. Constant/multiple annoying tone/voice PA announcements of mentioning "... only big/large suitcases are for the bin and small ones need to be placed under the seat, etc,..." I see that flight was delayed and crew were trying to get the plane ready to board as soon as they can but the way they presented was lack of better word, condesending and scolding tone to cattle. It was definite unpleasant, unwelcoming flight experience I have ever had with Jetblue. Whatever happen to smiles and fun employees , pleasant/helpful gate agents, flight attendants, crews, where have they gone? It was dissapointing flight experience overall from everyone. Sorry for the direct transparency.

Flight was cancelled as JetBlue could not find a pilot. Communication was poor and they did nothing for stranded passengers. Flight they rebooked us on was 4 days out.

JetBlue cancelled the flight. We had to rebook on another airline.

JetBlue cancelled the flight along with hundreds of others, for no apparent reason. no recourse, no rebooking options. never booking with them again

Jet Blue cancelled my flight after I had boarded. They attempted to rebook me for a new flight two days later. I was able to rebook with a different airline, but not until the next morning. As such, I was forced to get an expensive hotel and missed important work meetings Monday morning. I am very disappointed with the customer service and will be pursuing full reimbursement for my hotel cost.

You did a great job rescheduling my cancelled flight. However, you made me pay for two seats for $118 even though the seats on the original flight were free. I think that was a very unfair thing to do.

They cancelled the flight after 5 hours at the airport and the only flight they offered was for the next day with a 7.5 layover in fll. This was not going to work for me as this was only a weekend trip and getting into providence at 10 pm a day later caused me to lose Mo ey on hotels money on airport parking a dog sitter etc. they wouldn’t offer any type of a voucher or anything else. All they did was refund the flight which didn’t help me with all the money in time I lost. I was going to see my very sick father

The flight was on time the crew was courteous that makes for a good flight.

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

Everything you need to know for your flight to Caribbean Islands

Information on your arrival and departure airports