$72 Find Cheap Flights from Hartford to Caribbean Islands

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 2/23. 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.
1 adult
1 adult, Economy, 0 bags

KAYAK searches hundreds of travel sites at once for deals on flights to Caribbean Islands

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Hartford to Caribbean Islands.
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Hartford to Caribbean Islands.
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Cheap Flights from Hartford to Caribbean Islands

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Punta Cana
Punta Cana2 stops$329
Santo Domingo
Santo Domingo1 stop$325
Montego Bay
Montego Bay2 stops$332
Oranjestad
Oranjestad1 stop$335
Nassau
Nassau2 stops$324
Kingston
Kingston1 stop$424
Simpson Bay
Simpson Bay1 stop$267
Providenciales
Providenciales1 stop$321
Port of Spain
Port of Spain2 stops$274
Bridgetown
Bridgetown1 stop$340
George Town
George Town2 stops$288
Willemstad
Willemstad1 stop$279
St. John's
St. John's1 stop$514
Puerto Plata
Puerto Plata1 stop$500
Aguadilla
Aguadilla1 stop$244
Punta Cana
Punta Cana2 stops$329
Santo Domingo
Santo Domingo1 stop$325
Montego Bay
Montego Bay2 stops$332
Oranjestad
Oranjestad1 stop$335
Nassau
Nassau2 stops$324
Kingston
Kingston1 stop$424
Simpson Bay
Simpson Bay1 stop$267
Providenciales
Providenciales1 stop$321
Port of Spain
Port of Spain2 stops$274
Bridgetown
Bridgetown1 stop$340
George Town
George Town2 stops$288
Willemstad
Willemstad1 stop$279
St. John's
St. John's1 stop$514
Puerto Plata
Puerto Plata1 stop$500
Aguadilla
Aguadilla1 stop$244

Book Cheap Hartford to Caribbean Islands Plane Tickets

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Hartford to Caribbean Islands that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Hartford to Caribbean Islands

Wed, Mar 4 - Sat, Mar 7
Frontier Logo
10:19 am - 12:43 am
BDL
-
SJU
13h 24m
1 stop
Frontier Logo
6:00 am - 9:15 am
SJU
-
BDL
4h 15mnonstop
$189Frontier
Tue, Mar 3 - Tue, Mar 24
Frontier Logo
7:55 pm - 12:46 am
BDL
-
SJU
3h 51mnonstop
Frontier Logo
6:00 am - 10:15 am
SJU
-
BDL
4h 15mnonstop
$190Frontier
Sun, Mar 8 - Thu, Mar 12
United Airlines Logo
6:00 am - 2:57 pm
BDL
-
SXM
8h 57m
1 stop
United Airlines Logo
3:55 pm - 9:32 am
SXM
-
BDL
17h 37m
1 stop
$267United Airlines
Sun, Mar 8 - Thu, Mar 12
United Airlines Logo
6:00 am - 2:57 pm
BDL
-
SXM
8h 57m
1 stop
United Airlines Logo
1:52 pm - 9:32 am
SXM
-
BDL
19h 40m
2 stops
$272United Airlines
Wed, Apr 29 - Fri, May 8
American Airlines Logo
5:45 am - 3:22 pm
BDL
-
SXM
9h 37m
1 stop
American Airlines Logo
2:24 pm - 9:10 am
SXM
-
BDL
18h 46m
1 stop
$273American Airlines
Tue, Jun 23 - Wed, Jul 1
American Airlines Logo
7:20 am - 12:43 pm
BDL
-
SXM
29h 23m
1 stop
American Airlines Logo
4:43 pm - 10:24 am
SXM
-
BDL
17h 41m
2 stops
$277American Airlines
Sun, Apr 12 - Wed, Apr 15
Delta Logo
6:00 am - 3:10 pm
BDL
-
PLS
9h 10m
1 stop
Delta Logo
3:25 pm - 11:59 pm
PLS
-
BDL
8h 34m
1 stop
$321Delta
Thu, Apr 9 - Wed, Apr 15
Delta Logo
7:12 pm - 11:55 am
BDL
-
AUA
16h 43m
1 stop
Delta Logo
3:25 pm - 11:59 pm
AUA
-
BDL
8h 34m
1 stop
$335Delta
Fri, Apr 24 - Fri, May 8
JetBlue Logo
8:00 pm - 8:26 am
BDL
-
SDQ
12h 26m
1 stop
JetBlue Logo
3:01 pm - 11:54 pm
SDQ
-
BDL
8h 53m
1 stop
$343JetBlue
Sat, Mar 21 - Wed, Mar 25
JetBlue Logo
8:23 pm - 8:32 am
BDL
-
SDQ
12h 09m
1 stop
JetBlue Logo
7:33 pm - 9:13 am
SDQ
-
BDL
13h 40m
1 stop
$353JetBlue
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 72 hours was to San Juan, at $167 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 72 hours was $167.

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 $355, 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 March, when tickets cost $280 (return) on average. On the other hand, the most expensive months are December and July, when the average cost of round-trip tickets is $430 and $366 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 Sunday and more expensive on a Friday. On your return trip to Hartford, you should consider flying back on a Sunday, and avoid Mondays 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 2 weeks before departure, which saves you about 10% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 5 weeks before departure.

Good to know

Low seasonSeptember
Cheapest flight$68
Best time to beat the crowds with an average 11% drop in price.
Most popular time to fly with an average 10% increase in price.
Flight from Hartford to San Juan Airport

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.

  • 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 evening, when round-trip flights cost $320 on average. Morning departures are around 17% more expensive than evening flights, on average. The most expensive time of day to fly to Caribbean Islands is generally in the afternoon, which is peak travel time and where the average cost of a ticket is $408.

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 $120 one-way - $276 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.
7.9
DeltaOverall score based on 8214 reviews
7.9Comfort
8.5Crew
7.8Entertainment
7.2Food
8.1Boarding
Airline reviews

Terrible. Four hour delay because Delta could not find crew to man the aircraft. Terrible communication. Terrible insight into the delays. One of the worst flight experiences I’ve had.

2.0 MediocreDonna, Feb 2026
DEN - LGA
Read more Delta reviews

Terrible. Four hour delay because Delta could not find crew to man the aircraft. Terrible communication. Terrible insight into the delays. One of the worst flight experiences I’ve had.

It was good. The leg room was not great in Row 1.

The landing was the worst I’ve experienced with a flight.

The crew, and fellow passengers, were super gracious and kind. There seemed to be plenty of bin space even though the plane was full. It’s nice to get a glass of wine with dinner in Premiere seating, and there was a lot of food.

First flight out and was 85 minutes delayed. Notification came out way too late

Delta flights recently are always delayed AND at jfk tney get the gates further away (need To walk 20’ to get to them/all the way at the end of the terminal). Not sure whats happening but price doesnt match experience!

Everything I mentioned earlier - the airbus was more comfortable indeed and the experience was further enhanced.

Delta continues to set the benchmark for traveler-friendly service with minimal disruption and clear communication within the mainland US (coast to coast). I am consistently pleased to be a Delta customer, and this experience once again met my expectations. There was a brief delay departing from MIA due to a technical issue that required the aircraft to return to the gate. However, the situation was handled professionally and transparently. Fortunately, my planned layover allowed ample buffer time, so the adjustment caused no stress. Overall, another smooth and reassuring experience.

Good experience and the flight landed early. There was no food I had or entertainment.

Flight was delayed and no reasons provided. After the passengers were boarded, the crew made announcement that the captain has jot arrived and he would take another 15 mins. All passengers patiently sat until the captain came and started. Terrible experience!

Flight was smooth. We boarded early and left Grand Rapids about a half hour ahead of schedule. We then arrived in Lakeland about 40 minutes early. Flights attendants (3) were welcoming and pleasant. Wish we would have at least been offered to buy a bottle of water. No beverage service at all.

I really liked the young man who checked me in and took my bags! He was so kind and was very helpful! I told my sister about the great service and him and she said that is why she flies Avelo Air.

The flight was delayed by a lot and the seats are pretty tight

Surprisingly was one of the better flights I’ve been on

Short 2-hour flight, we took off on time, ETA was earlier than stated, no interaction needed with stewards, no food, no entertainment on such a short flight.

Avelo provided exactly what I expected. They are a low-cost option with no frills but the experience was comfortable and the staff was great! I will be using them in the future for trips when cost is a priority for me.

Expect nothing and you will be fine. Seats are crammed.

Terrible landing. Uncomfortable seats. Great cabin crew-helpful and pleasant!

Tight fit in middle seat but OK for short flight. Crew was more interested in talking to each other than helping passengers - strickingly dissappointing. DAB is a great airport. New Haven sucks! Excellent value for the .

Avelo is definitely a budget airline and you get what you pay for. The plane was packed and the seats were not particularly comfortable. Staff was very nice and both of our flights were on time. The one thing I wish I had known was that the staff does not show up at the airport desk to check your bags until two hours before the flight. We had a 4:30 flight and had to check out of our hotel at noon. Since we have lounge passes we planned to check our bag, go through security and hang out at the lounge until we had to board. But because we could not check our bag until 2:30, when the staff showed up, we could not go through security and access the lounge. Passengers with boarding passes and carry on luggage would not have this issue. I might fly Avelo again but would only do carry on or plan to get to the airport no sooner than two hours before check in. And I would not recommend a long flight on Avelo since there is no food or entertainment and the seats are not comfortable.

it was a very short flight so my expectations were low.

As great a red-eye flight as red-eye flights can be.

Once boarding started it was pretty quick. Food was inedible; cold and salty..

Entertainment kept turning itself off. Gave up on watching a movie.

Both the WIFI and entertainment did not work for 2.5h

The crew made our experience extremely bad. They were rude and didn’t have anything for kids.

Very old flight - time to retire it for newer airplanes

2+ hours delayed Outlet in row 12 did not work Tv monitors did not work Lights kept off the entire flight for at 5pm-7pm flight

Very disappointing given gate agent behavior. Filed a formal complaint with United.

Do not like the size of the overhead bin. I think staff should monitor the size of suitcases that are being carried on by passengers to ensure they meet the size requirement.

Everything was good. Flight was very full so crew was busy. After we boarded and plane pulled away from the gate, we were delayed about 40 minutes- sitting on the runway - due to weather en route or at the destination. While weather is not the fault of the airline- it’s terrible to sit on a plane and not moving.

We missed our flight and got stranded in Miami where we had to rent a hotel we could not afford. they would not work with us because they said it was weather related even though the gate attendant said it was not. I could go on but trying to get satisfaction has wore me down, which I believe is the intent. My only solution is to never fly AA again.

No Snacks or Entertainment. The flight was short, snacks should still be given.

We lost a day of our vacation because AA did not get the plane to the gate on time. Even though the gate attendant was very clear that it was not weather related, AA would do nothing because there was some snow that day. They basically said the gate attendant was wrong even though she was on the front line of the situation and they were not.

See prior comment about how Kayak mishandled my reservation and delayed my arrival by 6 hours.

American Airlines was great and worked very hard to change my ticket so I could get an earlier, direct flight back to Dallas. However, I was informed that Kayak made mistakes with my itinerary and classified my ticket as desiring to be on the earlier flight instead of taking the necessary step of calling AA to get me on the standby list. This ended up keeping me from being added to the standby list and delayed me getting home by 6 hours. I am happy to discuss this further with Kayak so they can correct their procedures so this won't happen again.

The flight was fine. It's the satellite terminal that supports American eagle flights is what sucks. There is only one food option and everything there is way overpriced. I mean I know it's airport pricing, but it's even crazier than that. I bought a sandwich in a plastic container for $18.

Overall it was a good flight. Because we traveled on a Saturday we were upgraded to FC since my wife and I are both Executive Platinum. The only areas for improvement we noted are better snack assortment and perhaps a little nicer plane as American is flying some older planes now. Everything else on this flight was excellent, which is frankly not the norm for American since we have had multiple issues on prior AA flights.

The smell from the bathroom kept wafting through the cabin. It made people sick.

The flight was really crowded. Flight attendants were just ok.

My flight got delayed and eventually canceled, then rescheduled. I and several others had a connection from Boston to Paris and asked several times if we would make it. They assured us we would and then rebooked us mid flight without our consent and closed doors early even though they said they communicated we were a bit delayed. We got stranded in Boston and I opted with being rebooked for a different connection to France since they refused to pay for a Hotel. I've now been in Europe for 5 days and still haven't recieved my bags. There was absolutely no urgency for the fact that I'm in a foreign country with absolutely no change of clothes or any of my medication. Such an overwhelming and frustrating experience.

Automated scanning was slow and somewhat haphazard. Too many people were unfamiliar with the tech and were forced to learn on the fly. The hands off approach of the gate staff made it more uncomfortable. This needs work. Overall the flight and cabin crew were excellent.

The crew for the flight was A+ top notch. They were friendly and professional and made the flight a very relaxing and enjoable.

Rude crew member. She seemed annoyed at me without me saying a single word. Also loudly admonished me for having my bag next to my seat instead of tucked away before landing. Just telling me to put it away and guiding me without giving me a lecture would have been enough.

No included food for a 5 hour flight and the entertainment was only accessible if you had wired headphones (not provided). Otherwise though, great and smooth flying and customer service.

Crew were fantastic and so catering and wonderful! Full score for the entire crew!

Because of weather and mechanical issues our flight was 4 hours late. The only compensation offered to us was a meal voucher to be used only at Boston Airport and only on the day issued. But by the time it was offered to us all the restaurants were closed, so there was no way to use that offer.

Friendly crew, efficient boarding and flight arrived early. Couldn’t ask for a better experience

Terrible. They canceled our early morning flight after midnight on the day of and had no available flights to rebook my family on for the next 72 hours. Yet they still had other flights that were not cancelled from JFK so it couldn’t be based on the weather. It felt like they canceled the flight based on it not being profitable enough for them. I am not interested in traveling with the again. The absolute worse customer service and lack of accountability.

Horribly rude check in at airport, worst in 25 years of flying. All over a simple issue they could have googled to resolve.

Everything you need to know for your flight to Caribbean Islands

Information on your arrival and departure airports