$78 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 1/19. 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$282
Santo Domingo
Santo Domingo2 stops$323
Montego Bay
Montego Bay1 stop$331
Oranjestad
Oranjestad1 stop$304
Nassau
Nassau1 stop$301
Kingston
Kingston1 stop$408
Simpson Bay
Simpson Bay1 stop$249
Providenciales
Providenciales1 stop$386
Port of Spain
Port of Spain2 stops$383
Bridgetown
Bridgetown1 stop$295
George Town
George Town1 stop$280
Willemstad
Willemstad1 stop$230
St. John's
St. John's1 stop$421
Puerto Plata
Puerto Plata1 stop$436
Aguadilla
Aguadilla1 stop$181
Punta Cana
Punta Cana1 stop$282
Santo Domingo
Santo Domingo2 stops$323
Montego Bay
Montego Bay1 stop$331
Oranjestad
Oranjestad1 stop$304
Nassau
Nassau1 stop$301
Kingston
Kingston1 stop$408
Simpson Bay
Simpson Bay1 stop$249
Providenciales
Providenciales1 stop$386
Port of Spain
Port of Spain2 stops$383
Bridgetown
Bridgetown1 stop$295
George Town
George Town1 stop$280
Willemstad
Willemstad1 stop$230
St. John's
St. John's1 stop$421
Puerto Plata
Puerto Plata1 stop$436
Aguadilla
Aguadilla1 stop$181

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
Thu, Feb 19 - Mon, Feb 23
Frontier Logo
11:02 am - 10:10 am
BDL
-
PSE
22h 08m1 stop
Frontier Logo
11:30 am - 8:53 am
PSE
-
BDL
22h 23m1 stop
$182Frontier
Sun, Feb 22 - Sat, Feb 28
Frontier Logo
7:55 pm - 12:46 am
BDL
-
SJU
3h 51mnonstop
Frontier Logo
5:25 pm - 10:37 am
SJU
-
BDL
18h 12m1 stop
$192Frontier
Fri, Jan 23 - Fri, Jan 30
JetBlue Logo
6:00 am - 4:21 pm
BDL
-
SXM
9h 21m1 stop
JetBlue Logo
5:36 pm - 11:48 pm
SXM
-
BDL
7h 12m1 stop
$249JetBlue
Mon, Feb 2 - Sun, Feb 8
JetBlue Logo
6:00 am - 2:28 pm
BDL
-
SXM
7h 28m1 stop
JetBlue Logo
5:36 pm - 11:43 pm
SXM
-
BDL
7h 07m1 stop
$261JetBlue
Fri, Jan 23 - Fri, Jan 30
American Airlines Logo
7:40 pm - 2:22 pm
BDL
-
SXM
17h 42m2 stops
American Airlines Logo
4:24 pm - 8:59 am
SXM
-
BDL
17h 35m2 stops
$262American Airlines
Mon, Mar 2 - Mon, Mar 9
American Airlines Logo
6:00 am - 2:16 pm
BDL
-
SXM
7h 16m1 stop
American Airlines Logo
4:01 pm - 2:51 pm
SXM
-
BDL
22h 50m1 stop
$263American Airlines
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
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
$288Delta
Thu, Jan 15 - Sun, Jan 18
Avelo Airlines Logo
6:30 am - 10:43 am
BDL
-
MBJ
4h 13mnonstop
Avelo Airlines Logo
11:43 am - 3:38 pm
MBJ
-
BDL
3h 55mnonstop
$346Avelo 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 $154.

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 $337, 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$78
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 $163 one-way - $257 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 8022 reviews
7.9Comfort
8.1Boarding
7.2Food
8.5Crew
7.8Entertainment
Airline reviews

This flight was no comparison to our prior flight. I'm thinking it all has to do with the age of the aircraft.

10.0 ExcellentAnonymous, Dec 2025
DCA - SEA
Read more Delta reviews

This flight was no comparison to our prior flight. I'm thinking it all has to do with the age of the aircraft.

This flight was a first class choice and left much to be desired. Seat backs on seats were falling apart and torn. Seats actually didn't come to a "full & upright position". Pull out table was sprung. Not any significant leg room. All in all we were on an obviously older plane and felt overcharged for what we received as first class.

A 12 hour flight during the day with one real meal service - are you kidding? Also the breakfast was one of the worst and not what was listed

Flight was delayed several times. At one point, they "pulled back" 15 minutes from the delayed boarding and sent a text saying we would board sooner than previously advised. The flight then was delayed again. And when we boarded, there was an unspecified technical issue which had us waiting in the plane for about an hour.

Delta is a good airline. I've never had an issue with Delta. I'll continue to fly with them until they show me that I shouldn't.

The only thing nice I can say is the flight crew was really nice and apologetic about the situation. They shared as much information as they had and advised us on what we could do about missing connecting flights. The boarding process was so slow. The gate agent was working by herself and should have had someone working with her. It took almost an hour to board because she was trying to board a full flight of people and provide customer service to everyone who was flying standby and/or had questions. It was really chaotic. This didn't help the fact that we were delayed and folks were missing connections the longer it took.

The gate attendants and the crew were terrible. Because of high winds, they needed to carry more fuel, so they had to get volunteers to take the next flight at 6 am the next day. They did a terrible job of it - our flight ended up taking off just under 3 hours of the scheduled time. I hope to never fly Delta again.

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

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.

The flight was delayed by two de-icings. The seatbelt did not work correctly. It did not stay tight.

Everything was absolutely wonderful from check in to baggage claim. Staff was very professional and sweet. Will definitely recommend United to family and friends.

Aircraft was noisy, old and never dimmed the lights on a night flight even on business class! I flew 17 times on United and probably another 40 on other airlines United USA /Europe flights were the worst to include luggage delayed once going to europe and once coming back

Check how old the airframe is, some older ones have inoperable seat back entertainment or power.

Sitting on the runway after we land for almost two hours! Not sure if we should blame United or Just Dumpy Vance.

Hotter than Hades in August. Why, why do crews think that in the winter when we are already dressed for cold weather we need a cabin that is 82 degrees. Even the vents were blowing hot air.

Unbelievably poor service from flight attendants. They didn’t even do water service on a four hour flight. Just disrespectful.

United is an incompetent airline. They parked the plane on the tarmac for an hour after arriving because they “didn’t have a gate available” it was actually some sort of lie because as we de planed there were approximately 9 open and manned and empty gates that we walked past. Many people on the flight missed connections for the hour long sit on the tarmac. Utterly baffling and incompetent behavior from United flight ops.

Flight was delayed. De-icing took a while. When we landed had to wait for another plane to vacate our gate. Just an overall bad experience.

I understand weather is an issue, but making us chase our plane down at five scheduled gates across three terminals in an airport the size of O'Hare was unfair. They'd have probably been better off to leave gates as TBD until the inbound plane is in final approach instead of running us all over the place. Also, props to the consistently-unprepared ground crew in Richmond for once again leaving my lane parked short of the gate because they couldn't have a crew in place on time with 2 hours notice...

Crew were all friendly and helpful. It was a short flight so just a beverage service with a cookie. After we were boarded the plane took about 45 minutes to leave the gate but it was New Year’s Eve so not shocking there was some delay. Overall good experience and very grateful.

After the door had been closed, the cockpit makes an announcement that catering is running late and it is not the airline's fault. It is their fault in the sense that we had to sit for 2 hours or more when we could have stayed in the terminal. Poor communications between catering and airline. This caused a young man to lose his temper and he went storming out hitting objects. He had complained to the gate agent that he had already waited at the gate 7 hours and when can the airplane leave? Airilnes do a poor job of explaining delays, maintenance issues, etc. whereas being truthful may gain more sympathy or understanding.

The flight was very smooth and the meal in business class was great.

The captain brought my 6 year old son into the cockpit and allowed him to ask questions, sit in the captain’s chair and talk about all the gears and levers. Made the trip very special for him.

I take this flight about 6-8 times per year. It is convenient and saves an hour or two by skipping PDX, SEA, PHX, or ORD (but it takes longer to get bags to the carousel than Alaska Airlines). I wish the food service were better (but they might cut back on it because it is a red-eye). The WifI seems to go down about an hour out of Anchorage, and then comes back about an hour later...so be warned if this is an issue for you.

Better service. No food options, but we did get drinks and a cookie.

Boarding was organized and timely. Food was mediocre, especially for first class travel.

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.

1) No pilot available for 1 hour 2) no room for most passengers careyon in overhead—-> stowed below 3) when we landed we had to wait 45 min. Before docking at gate as gate was not ready

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.

Everything you need to know for your flight to Caribbean Islands

Information on your arrival and departure airports