$96 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 5/9. 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 Cana1 stop$252
Santo Domingo
Santo Domingo2 stops$358
Montego Bay
Montego Bay1 stop$343
Oranjestad
Oranjestad1 stop$361
Nassau
Nassau1 stop$400
Kingston
Kingston1 stop$499
Simpson Bay
Simpson Bay1 stop$339
Providenciales
Providenciales1 stop$505
Port of Spain
Port of Spain1 stop$312
Bridgetown
Bridgetown1 stop$374
George Town
George Town1 stop$296
Willemstad
Willemstad1 stop$321
Puerto Plata
Puerto Plata1 stop$610
Aguadilla
Aguadilla1 stop$186
St. John's
St. John's1 stop$550
Punta Cana
Punta Cana1 stop$252
Santo Domingo
Santo Domingo2 stops$358
Montego Bay
Montego Bay1 stop$343
Oranjestad
Oranjestad1 stop$361
Nassau
Nassau1 stop$400
Kingston
Kingston1 stop$499
Simpson Bay
Simpson Bay1 stop$339
Providenciales
Providenciales1 stop$505
Port of Spain
Port of Spain1 stop$312
Bridgetown
Bridgetown1 stop$374
George Town
George Town1 stop$296
Willemstad
Willemstad1 stop$321
Puerto Plata
Puerto Plata1 stop$610
Aguadilla
Aguadilla1 stop$186
St. John's
St. John's1 stop$550

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

Mon, May 4 - Fri, May 8
Frontier Logo
8:42 pm - 2:08 am
BDL
-
SJU
29h 26m
1 stop
Frontier Logo
3:03 am - 6:58 pm
SJU
-
BDL
15h 55m
1 stop
$185Frontier
Sat, May 2 - Sat, May 9
Frontier Logo
5:42 pm - 2:01 am
BDL
-
SJU
8h 19m
1 stop
Frontier Logo
6:00 am - 6:58 pm
SJU
-
BDL
12h 58m
1 stop
$186Frontier
Tue, May 5 - Tue, May 12
American Airlines Logo
7:23 pm - 1:15 pm
BDL
-
STT
17h 52m
2 stops
American Airlines Logo
1:15 pm - 11:41 pm
STT
-
BDL
10h 26m
2 stops
$280American Airlines
Sat, May 16 - Sat, May 23
American Airlines Logo
7:23 pm - 1:15 pm
BDL
-
STT
17h 52m
2 stops
American Airlines Logo
1:47 pm - 11:26 pm
STT
-
BDL
9h 39m
1 stop
$317American Airlines
Thu, May 14 - Fri, May 22
JetBlue Logo
6:00 am - 3:22 pm
BDL
-
SXM
9h 22m
1 stop
JetBlue Logo
3:11 pm - 11:36 pm
SXM
-
BDL
8h 25m
1 stop
$339JetBlue
Wed, May 6 - Tue, May 12
Delta Logo
6:00 am - 2:48 pm
BDL
-
STT
8h 48m
1 stop
Delta Logo
3:01 pm - 12:33 am
STT
-
BDL
9h 32m
1 stop
$341Delta
Tue, Apr 28 - Sat, May 2
JetBlue Logo
6:00 am - 11:38 am
BDL
-
MBJ
6h 38m
1 stop
JetBlue Logo
8:41 am - 7:53 pm
MBJ
-
BDL
10h 12m
1 stop
$343JetBlue
Fri, May 8 - Fri, May 15
United Airlines Logo
10:33 am - 3:10 pm
BDL
-
MBJ
5h 37m
1 stop
United Airlines Logo
4:12 pm - 11:44 pm
MBJ
-
BDL
6h 32m
1 stop
$352United Airlines
Fri, May 8 - Wed, May 13
United Airlines Logo
10:33 am - 3:10 pm
BDL
-
MBJ
5h 37m
1 stop
United Airlines Logo
2:40 pm - 9:37 am
MBJ
-
BDL
17h 57m
2 stops
$357United Airlines
Wed, Apr 29 - Thu, May 7
Delta Logo
7:00 am - 2:10 pm
BDL
-
AUA
7h 10m
1 stop
Delta Logo
3:25 pm - 12:33 am
AUA
-
BDL
9h 08m
1 stop
$371Delta
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 $178 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 $178.

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 evening, when round-trip flights cost $345 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 at night, which is peak travel time and where the average cost of a ticket is $383.

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 $373, 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 $303 (return) on average. On the other hand, the most expensive months are December and February, when the average cost of round-trip tickets is $427 and $382 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 Friday, 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 7% 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$96
Best time to beat the crowds with an average 13% drop in price.
Most popular time to fly with an average 8% 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.

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 $158 one-way - $329 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 8423 reviews
8.5Crew
7.9Comfort
7.2Food
8.1Boarding
7.8Entertainment
Airline reviews

Very old plane with no inflight entertainment. I purchased the internet pass and it was nearly unusable.

6.0 GoodCarlos, Apr 2026
ICT - ATL
Read more Delta reviews

Very old plane with no inflight entertainment. I purchased the internet pass and it was nearly unusable.

My tray was broken so i had no place to work or eat except my lap. Flight attendant said I would get an email with some credit or miles, it was a complete waste of time as I could only function at about 20% of normal. I have not received anything yet.

Short trip, no food and therefore no expectation for much interaction with staff who were pleasant and professional. My critique is on comfort of the seats. Exit rows and comfort seats do not provide enough personal space for 3 side-by-side seats, especially when in the middle row. Some passengers are not considerate of the middle seat and there should be signs that state something to the effect of: "please consider giving middle seats use of the armrests."

My flight yesterday evening was delayed 3.5 hours with no water or food service. Poor experience

Transparency from pilots, quick boarding and exiting the plane, staff greeted to each and everyone,

Didn't like sitting on the waiting pad for 30 minutes right after departing the gate. If you're going to do that, just don't board so people can still get up and walk around in the terminal. My luggage was damaged by the baggage handlers.

Pilots lied about waiting on “paperwork”. Sat in the plane for over an hour, waiting on some papers to be printed according to the pilot and then all of a sudden he says good news maintenance is finally on their way. Maybe they can fix it before we get our paperwork. Ended up missing my connection in LaGuardia and as a result, had a fly home to Lexington instead of the Louisville airport. Then paid $100 to uber to Louisville since it was midnight by the time I got in. I wish they would just be transparent with passengers sometimes and not try to beat around the bush on why things are delayed.

The WiFi was horrific. I fly delta often and love their (usually reliable and free) WiFi. On this flight it was intermittent and when it did connect was extremely slow. I couldn’t get any work done while I was on the flight which was extremely frustrating. I was also in the exit row seat where there is now immediate seat in front of you, so while the leg room was nice, I couldn’t even watch the TV when the internet wasn’t working. Finally, for the last 20 mins of the flight, the announcement indicator came on the TV screens and took them over, even though no announcement was being made. Really disappointed.

The flight was way too HOT! And the plane did not have any in-flight TV entertainment.

Boarding was good. The flight was on time ( arrival was 20 minutes early). Inflight service was average ( US airlines have not mastered the skills of customer service yet). The food was mediocre. “ breakfast “ was downright awful and insulting. It was a piece of dough with mon descript filling that was supposed to be cheese omelette).

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.

My bags were misplaced!!! Im in a foreign country with no bags

The entertainment options on the seat back video boards were nice.

The flight I was supposed to be on was supposed to take off at 1:50 from State College. It was delayed over and over and over again until somehow I had to rebook on a flight that was supposed to have left State College at 8 am that morning but didn't end up taking off until almost 6 pm. Not only was this completely unacceptable, the "token from United" was a 15 dollar meal voucher that has to be used by today. I would personally like some miles added to my account for this inconvenience. I was in transit for 8 hours from the time I arrive at State College Aiport to when I got home. I was supposed to be home at 3 pm and I returned at 8 pm. Unacceptable. I have not been on an on Time united flight in nearly 5 years.

Crew was friendly. Seats are too narrow, particularly when a big person is in the adjacent seat, but I understand this is due to smaller planes usually flight into Lincoln. I have experienced several flight delays going out and coming into Lincoln airport, I say maybe 50% or higher of the flights I've taken out of this airport have been delayed.

newer aircraft, ability to connect my headset via blue tooth for entertainment.

Great flight. Boarded efficiently. Arrived early at CLT. There was no in flight entertainment on this aircraft. Great crew.

Due to cancellation of connecting flight (Lufthansa) I didn’t fly with United

The seat was comfortable. There was a lot of turbulence. If it weren't for that,it would have been okay.

It was a red-eye, but the flight felt surprisingly quick. The seats were very comfortable, and that made resting much easier. I also want to thank the gentleman seated next to me, who graciously moved so my mom could sit beside me. We slept almost the entire way. The cabin crew was respectful in not disturbing us, while also being courteous and professional throughout. Thank you, United.

Packed in plane small uncomfortable seats elbow to elbow nobody wants to be in that situation for the money they paid

Entertainment and wifi were very sub-par - audio issues and no wifi

We were delayed and had to circle due to weather and had to divert for fuel. While I understand that you can’t control the weather I would have appreciated knowing that the crew wasn’t going to run out of hours and then having to spend the night in the Raleigh airport.

Messy plane that was falling apart Small screens that didn't work

I was traveling with two small kids and our TV s were the only ones not working. Informed the flight attendant who did nothing about them.

They forced me to check my hand luggage at the gate.

I specifically choose not to check bags to ensure I can proceed directly to ground transportation upon arrival. However, due to a recurring lack of cabin space, I was again forced to gate-check my rolling luggage after going through my luggage to take out electronics and batteries. This practice unilaterally changes the service agreement made at the time of purchase. JetBlue needs to find a better way to manage overhead space that honors the carry-on baggage allowance.

Still hasn’t left. Why are you asking how it was?

Flight was good wish there were more snacks options for such a long flight but stewardesses were very pleasant as was flight crew.

I was denied a plastic fork to eat my food and was told plastic forks are for paying customers who buy Jet Blue’s food. So I had to make a utensil out of a cup so nourish my body. Like a refugee. Because decency is dead.

I was especially impressed without efficiently the crew got passengers on and off. One of the stewards was slightly gruff, I thought. No big deal but that's what I noticed.

I was able to get the AA customer Service desk to put me on an earlier flight without any issues.

The seat was comfortable, the attendants were very nice and WiFi made my life so much easier with work. Kudos!

Flight was 3 hours delayed. They gave our plan to two other routes. Need to knock that off.

To have arrived on time and not 3 hours late after having already spent $100 to change to an earlier flight, only to arrive back home close to the original flight time.

No gate in Rome. Had stairs. Got separated from my wife in a wheel chair. Customs was a zoo. If AA doesnt have landing rights, it should be advertised.

I almost missed my flight and they helped me out enormously

Business class was very good, one of my best flights

The "on the ground" A/C was not working. It was so hot while waiting to get in the air, a passenger from the rear of the plan declared "I just can't!" and waited in the gangway until time to close the doors. It was miserable. But the crew were champs and had an amazing attitude. I know they were as miserable as we were but didn't let that affect their performance.

The captain announced to the cabin there would be a delay because they observed a "cut" on a tire during precheck that needed to be cleared by maintenance. We were delayed during this inspection and allowed to proceed after maintenance "measured the cut and decided it was acceptable". My complaint is not about the delay or due diligence. I wish the captain had been more generic when making his announcement. I was a nervous wreck all the way to Charlotte worried that we would have a blowout when landing!

The SFO Lounge crew were amazing. The bartender Faris was great. Thanks!

Everything you need to know for your flight to Caribbean Islands

Information on your arrival and departure airports