$88 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 2/17. 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$291
Santo Domingo
Santo Domingo1 stop$314
Montego Bay
Montego Bay1 stop$331
Oranjestad
Oranjestad1 stop$304
Nassau
Nassau1 stop$300
Kingston
Kingston1 stop$413
Simpson Bay
Simpson Bay1 stop$257
Providenciales
Providenciales1 stop$400
Port of Spain
Port of Spain1 stop$273
Bridgetown
Bridgetown1 stop$295
George Town
George Town1 stop$280
Willemstad
Willemstad1 stop$242
St. John's
St. John's1 stop$396
Puerto Plata
Puerto Plata1 stop$400
Aguadilla
Aguadilla1 stop$180
Punta Cana
Punta Cana1 stop$291
Santo Domingo
Santo Domingo1 stop$314
Montego Bay
Montego Bay1 stop$331
Oranjestad
Oranjestad1 stop$304
Nassau
Nassau1 stop$300
Kingston
Kingston1 stop$413
Simpson Bay
Simpson Bay1 stop$257
Providenciales
Providenciales1 stop$400
Port of Spain
Port of Spain1 stop$273
Bridgetown
Bridgetown1 stop$295
George Town
George Town1 stop$280
Willemstad
Willemstad1 stop$242
St. John's
St. John's1 stop$396
Puerto Plata
Puerto Plata1 stop$400
Aguadilla
Aguadilla1 stop$180

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

Thu, Feb 26 - Mon, Mar 2
Frontier Logo
6:00 pm - 10:10 am
BDL
-
PSE
15h 10m1 stop
Frontier Logo
11:30 am - 9:23 am
PSE
-
BDL
22h 53m1 stop
$181Frontier
Wed, Feb 25 - Sat, Feb 28
Frontier Logo
10:19 am - 9:54 am
BDL
-
SJU
22h 35m1 stop
Frontier Logo
3:53 am - 10:37 am
SJU
-
BDL
7h 44m1 stop
$191Frontier
Sun, Mar 1 - Wed, Mar 11
Delta Logo
7:00 am - 4:22 pm
BDL
-
STT
8h 22m1 stop
Delta Logo
3:00 pm - 11:55 pm
STT
-
BDL
8h 55m1 stop
$287Delta
Tue, Feb 3 - Tue, Feb 3
JetBlue Logo
6:00 am - 1:01 pm
BDL
-
PUJ
6h 01m1 stop
JetBlue Logo
3:12 pm - 9:16 pm
PUJ
-
BDL
7h 04m1 stop
$291JetBlue
Sat, Feb 21 - Sat, Mar 7
JetBlue Logo
5:55 pm - 2:00 am
BDL
-
PSE
7h 05m1 stop
JetBlue Logo
6:00 am - 12:02 pm
PSE
-
BDL
7h 02m1 stop
$296JetBlue
Mon, Feb 2 - Sat, Feb 7
Delta Logo
6:03 am - 4:09 pm
BDL
-
PUJ
9h 06m1 stop
Delta Logo
3:56 pm - 11:40 pm
PUJ
-
BDL
8h 44m1 stop
$302Delta
Tue, Feb 10 - Wed, Feb 11
United Airlines Logo
6:00 am - 1:50 pm
BDL
-
AUA
6h 50m1 stop
United Airlines Logo
5:50 pm - 11:44 pm
AUA
-
BDL
6h 54m1 stop
$304United Airlines
Tue, Jan 20 - Sat, Jan 24
American Airlines Logo
7:40 pm - 4:50 pm
BDL
-
AUA
20h 10m2 stops
American Airlines Logo
4:50 pm - 11:04 am
AUA
-
BDL
19h 14m2 stops
$308American Airlines
Mon, Jan 26 - Mon, Feb 2
American Airlines Logo
1:22 pm - 1:51 pm
BDL
-
PUJ
23h 29m1 stop
American Airlines Logo
4:31 pm - 11:47 pm
PUJ
-
BDL
8h 16m1 stop
$308American Airlines
Tue, Feb 24 - Sat, Feb 28
United Airlines Logo
6:00 am - 3:22 pm
BDL
-
NAS
9h 22m2 stops
United Airlines Logo
12:55 pm - 11:59 pm
NAS
-
BDL
11h 04m2 stops
$317United Airlines
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 Punta Cana, at $97 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 $156.

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 $336, 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 $259 (return) on average. On the other hand, the most expensive months are December and July, when the average cost of round-trip tickets is $411 and $361 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 Thursdays 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 8% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 8 weeks before departure.

Good to know

Low seasonSeptember
Cheapest flight$88
Best time to beat the crowds with an average 14% drop in price.
Most popular time to fly with an average 5% 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 $284 on average. Morning departures are around 33% 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 $389.

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 $143 one-way - $262 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 8016 reviews
8.1Boarding
7.3Food
7.9Comfort
8.5Crew
7.9Entertainment
Airline reviews

Did not realize internet screen was hidden between seats and no info printed!!!!

6.0 GoodAnonymous, Dec 2025
BOS - MSP
Read more Delta reviews

Did not realize internet screen was hidden between seats and no info printed!!!!

2 of the seats in row 31 the entertainment system was not working, and one seat the tray table did not go all the way down. Flight arrived early and departed on time which was great.

Very good flight crew and very nice people staff were incredible especially the gate agent

Waited at the usual crowded gate at DCA where one ends up standing up because there aren't enough seats.

The flight was delayed for about 2 hrs. Other than it, it was good.

Advertised fruit trays with cheese, but only snacks handed out!

The plant way delayed departing by 3 hours. It was an old airplane with broken seats and armrests. The bathroom made a hollering sound. A really crappy flight experience and travel day all around.

Flight delays both to Detroits and return flight . The flight to Detroit was associated with mechanical difficulty

I am extremely disappointed that delta internal pilot manuals now refer to the Gulf of Mexico as the “gulf of America”. You can bow down to the Orange turd on your own. I will never fly delta again

Wasn't a Delta issue I don't think, but seems there was a Delta flight at each of the 2 Dallas airports at the same exact time, both to Atlanta. I was evidently booked on the one at Love Airport, but the Carey transport shuttle took me to DFW instead and I ended up missing the flight by just a few minutes. Was able to book a Southwest flight from Love Airport, but was a big loss of time and an inconvenience.

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.

No food or entertainment, but flight very comfortable and on time.

Sat next to a one year old. She crawled all over the place and made me laugh.

Not United Airlines' fault. It's ORL airport's fault.

Great flight. On time boarding. Smooth flight and on time arrival at EWR. The flight crew was marvelous and there was a great selection of movies on the entertainment system. Our bags were at the carousel before we got there. Another excellent flight from United.

United airlines has the best customer experience from booking to arrival. I always fly United airlines. The mileage program is excellent

They did the one thing that really matters - got to Chicago early.

I liked the snacks and the flight attendants were friendly.

Gate agent at Frankfurt was terrible. She denied PRE boarding even as it was printed on the boarding pass. Refused to look at the boarding pass and literally shouting for no reason. Frankfurt airport has horrible and rude staff who avoids trying to answer any question at all. Overall, horrible experience.

The Crew and the food was the worst I ever had in Business Class. First they told us there were no space for carry on. It was plenty of space over our 2 row seats, we had to ask to let us travel with it which was accepted. They were aware that we had to run for the connection due to the previous flight delay. Have us one hour waiting for more customers and not even offer a glass of water. Then started the service and they started to serve other passengers drinks in business and did not offer any drinks until they serve our pre ordered meal and I ask for something to drink. I had to wait until they finished to serve all passengers until Inget something. The crew was the worts I ever had for Business Class in my life.

Very turbulent trip made it pretty bearable, plus the lack of refreshments served and the lack of any air conditioning before takeoff which took an hour or more.

Flight was late - I was downgraded from first class to coach

We were 4+ hours delayed. AA is absolutely obnoxious. They just kept pushing back the time to the point where we did not get into Vegas until after midnight when we were supposed to arrive like 845pm.

My last flight on 25 Dec, it’s Christmas Day, everyone happy and very good mood. I really enjoy traveling with Americans Airlines from Miami to Minneapolis my home town after long flight from lhe to Doha then Miami. Thank you again to make my travels comfortable and relaxed. Best regards

The boarding process needs to be fixed. The zone don't work, especially when there is hardly anyone in zones 3, 4,and 5, leaving the majority of the passengers backed up in the aisle, especially because passengers seated near the front are blocking passengers who are seated in the rear of the plane. It would also help if the size of carry on bags was more strictly enforced.

I requested a low sodium meal. Reason being, I take medicine for high blood pressure and I wear compression socks on long flights to help with leg swelling. Having less sodium in meals really helps me feel better on long flights. I received my initial low sodium meal after takeoff. Just before landing, the crew came through with the meal cart and offered me what was being served. I said no thank you and then noticed my low sodium meal in the meal cart, with my name and seat assignment on it. I motioned to the crew member, but he grabbed the meal cart and proceeded to move to the rear of the aircraft. He didn’t see me or other passengers who had attempted to get this attention. He was more concerned about completing meal service since we were due to land in under 45 minutes. I pressed the call light five times from my seat to receive help, but no crew member responded to me. So, I didn’t receive a second meal, one that I requested (the low sodium option). This led me to have a migraine from only eating one meal on an 11-hour flight. This is why I’m not a fan of flying US-based airlines overseas. The crew members continue to show the absolute worst customer service experience. I would not recommend flying American for overseas flights.

WiFi didn’t work the entire flight. Very disappointing. Minimal food and options - sadly the state of current affairs. All other aspects of the flight were fine.

Great flight - friendly and attentive team! Seats in coach were comfy, but a little cramped - but that is the case with all airlines ;)

The boarding by groups is pointless. The first two groups worked fine, but almost Noone boarded in goups three thru five leaving the vast majority boarding when group six was called. It defeated the purpose of spreading out the crowd.

I don’t know who decides what food to serve on these flights but I would be so embarrassed if I served this to anyone and call it food…

For whatever reason, the flight was not catered -we were told it would be a 45 minute delay waiting for catering - so no food. There were opened candy and peanuts in the seatback pocket. Flight landed early in DFW but due to the assigned gate not being available, we sat on the ground for 30 minutes waiting for the gate to open - making the flight actually arrive at the gate late.

Not great. Booked Extra seats and got nothing extra at all. It’s basically a big budget airline.

Good. No issues except a slight delay. Crew came in late.

Not a pleasant experience, service was poor. Didn't like it

It was good. I prefer JB over other airlines.I just wish we had headphones for the films, but other than that - good.

The ride share experience in JFK is terrible. After traveling on a flight, then you need to take a subway to the last stop to get an uber or lyft. Unacceptable. Bad job JetBlue for permitting JFK and Port Authority to do this to your passengers.

Checking In on JetBlue site was impossible. It hung up on REAL ID. Even my Global Entry did not help. Luckily, on Kayak site it was a breeze. Entire flight the temperature was COLD! Otherwise the crew was great!

The flight was two hours late due to a computer fault and resulting maintenance. Nothing was offered as compensation beyond bottles of water during the time we were deplaned and waiting in the terminal.

Very pleasant flight attendants. Gate crew rather loud chatting with each other.

Four plus hour flight delay in New York caused us to take off after 11:30pm. We didn’t arrive at our hotel until five hours after check in. Started the trip off feeling exhausted.

Plane was in bad shape. TV’s and WiFi didn’t work. Plane need a refresh. Not enough room for bags.

There was a fowl odour coming from the lavatory the entire flight

Everything you need to know for your flight to Caribbean Islands

Information on your arrival and departure airports