$75 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 4/19. 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.
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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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Best Caribbean Islands Flight Deals from Hartford

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours

Punta Cana
Punta Cananonstop$276
Santo Domingo
Santo Domingo1 stop$335
Montego Bay
Montego Baynonstop$298
Oranjestad
Oranjestad1 stop$381
Nassau
Nassau1 stop$401
Kingston
Kingston1 stop$353
Simpson Bay
Simpson Bay1 stop$350
Providenciales
Providenciales1 stop$385
Bridgetown
Bridgetown1 stop$489
Port of Spain
Port of Spain1 stop$568
George Town
George Town2 stops$488
Willemstad
Willemstad1 stop$590
St. John's
St. John's1 stop$414
Puerto Plata
Puerto Plata2 stops$429
Aguadilla
Aguadilla1 stop$298

Cheap Flight Deals from Hartford to Caribbean Islands (BDL-zzEPX)

 
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.

Recent round-trip flight deals from Hartford to Caribbean Islands

Recommended round-trip deals departing in the coming months from the most popular airlines that fly from Hartford to Caribbean Islands.
Discover the best prices for you by selecting your travel dates on KAYAK.
Choose your dates
Frontier Logo
4:59 pm - 8:53 pmBDL-SJU
3h 54mnonstop
Frontier Logo
11:55 am - 3:59 pmSJU-BDL
4h 04mnonstop
$159Frontier
Find Deal
Sun, May 4 - Thu, May 8
Frontier Logo
4:59 pm - 8:53 pmBDL-SJU
3h 54mnonstop
Frontier Logo
11:55 am - 3:59 pmSJU-BDL
4h 04mnonstop
$160Frontier
Find Deal
Sun, May 4 - Thu, May 8
JetBlue Logo
8:40 am - 4:52 pmBDL-SJU
8h 12m1 stop
JetBlue Logo
8:55 pm - 12:52 amSJU-BDL
3h 57mnonstop
$253JetBlue
Find Deal
Tue, May 20 - Sat, May 24
JetBlue Logo
7:48 pm - 11:43 pmBDL-SJU
3h 55mnonstop
JetBlue Logo
8:35 pm - 12:31 amSJU-BDL
3h 56mnonstop
$258JetBlue
Find Deal
Sat, Apr 26 - Wed, May 7
United Airlines Logo
12:20 pm - 11:54 pmBDL-SJU
11h 34m1 stop
United Airlines Logo
7:25 am - 2:01 pmSJU-BDL
6h 36m1 stop
$265United Airlines
Find Deal
Wed, Apr 30 - Wed, May 7
United Airlines Logo
6:00 am - 2:44 pmBDL-SJU
8h 44m1 stop
United Airlines Logo
7:25 am - 9:49 pmSJU-BDL
14h 24m2 stops
$267United Airlines
Find Deal
Sun, May 4 - Sat, May 10
American Airlines Logo
6:14 am - 8:28 pmBDL-SJU
14h 14m1 stop
American Airlines Logo
5:30 am - 10:24 pmSJU-BDL
16h 54m1 stop
$272American Airlines
Find Deal
Mon, Apr 28 - Thu, May 1
American Airlines Logo
6:04 am - 3:00 pmBDL-SJU
8h 56m1 stop
American Airlines Logo
3:55 pm - 12:24 amSJU-BDL
8h 29m1 stop
$319American Airlines
Find Deal
Tue, Sep 2 - Tue, Sep 9
Delta Logo
6:00 am - 1:55 pmBDL-STT
7h 55m1 stop
Delta Logo
3:00 pm - 10:08 pmSTT-BDL
7h 08m1 stop
$319Delta
Find Deal
Mon, Sep 1 - Fri, Sep 5
Delta Logo
5:35 am - 12:45 pmBDL-SJU
7h 10m1 stop
Delta Logo
7:30 am - 4:04 pmSJU-BDL
8h 34m1 stop
$344Delta
Find Deal
Thu, May 8 - Tue, May 13

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?

The cheapest price for flight routes found by users searching on KAYAK in the last 2 weeks for round-trip flights from Hartford to Caribbean Islands.
The cheapest ticket to Caribbean Islands from Hartford found in the last 72 hours was to Montego Bay, at $123 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 $127.

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 $257 on average. Morning departures are around 48% 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 $380.

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 May, when tickets cost $219 (return) on average. On the other hand, the most expensive months are December and June, when the average cost of round-trip tickets is $408 and $297 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 Sunday. On your return trip to Hartford, you should consider flying back on a Wednesday, 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 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

High season

April

Cheapest flight

$75
Best time to beat the crowds with an average 21% drop in price.
Most popular time to fly with an average 1% 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.

See more FAQs

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 $130 one-way - $219 round-trip

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
DeltaOverall score based on 7897 reviews
8.2Boarding
8.5Crew
7.9Entertainment
7.3Food
7.9Comfort
Airline reviews

Simply outstanding. Their new lounge for Delta One customers is a cut above the rest.

10.0 ExcellentSunderesh, Mar 2025AUS - BOS
Read more Delta reviews

Simply outstanding. Their new lounge for Delta One customers is a cut above the rest.

The Dekta Rep that checked us in was great. She's very personable, pleasant, and can tell she enjoys her job.

After a 5 hour delay waiting at the gate (3 delays adding up) with no clear reason provided, we finally boarded flew 3/4 of the way to Toronto then were turned back to New York. As we neared New York, the pilot declared that it was his fault, something to do with timing and him not being allowed into the country???? How could the airline let his happen? They had hours to prepare and make sure they had a crew available for the flight! We ended up in Toronto a day late with no sleep.

The plane was old with small storage areas that had problems closing/latching and not enough storage for everyone, and worn, damaged seats. Service was great but feel a little unsafe on such well used planes.

Terrible and im avoiding them in the future. My initial flight was delayed causing me to rebook my flight and when speaking with the representative to rebook I explained this is the second time my flights were delayed and they did nothing to help me. I wasn't booked to comfort plus or given a voucher or anything. I was almost late for my meeting that I needed to attend on Monday because of the games delta played delaying my flights even more and putting me in the very back of the plane next to an extremely intoxicated passenger

Friendly flight attendants, smooth 8-9 hours flight. Economy seats are small and uncomfortable as usual.

Flights on time. .Ride was as comfortable as can be expected in steerage. Luggage arrived at destination. Attendants were fairly friendly.

Great staff. Wifi is terrible. Signing up for skylines is a painstaking process. Had to call customer service just to get my flight itinerary and confirmation sent to me. Consistent delays. A well staffed company that is run so poorly. Upper management needs to be renewed.

The WiFi didn't seem as fast as it normally is

Bathrooms dirty sinks clogged. No one seemed to clean them. Plane very old

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.

Baggage claim was barbaric at Wilmington. I realize that this is a startup airline but if they hope to grow or even survive they need to upgrade this airport. There is no automated luggage carousel and at times you are not only fighting your fellow passengers to get to your bags but also passengers coming in from other flights who cross right in front of you

No frills, i.e., no drinks or snacks. One is charged for everything. The cost really adds up. The crew and flight attendants were excellent and very pleasant.

I always walk by a pallet of Avelo branded mini bottles of water on the tarmac, but I’ve never seen them in flight. Yup, not even water offered on a 3 hour flight. No wi-fi onboard. We just watch the flight crew on their phone for 3 hours every flight. At least a mid-flight trash pickup would be great. Better than my last flight, but they only could have gone up from there. Don’t use for business or ticketed vacation like Disney… too unreliable.

You get what you pay for. The plane was dirty and the seats were awful.

Nightmare airline. Avoid Avelo. Understaffed at check-in with long, slow lines. Inexplicably had two flights and only one plane. Not weather or maintenance related apparently. One was supposed to go to Myrtle Beach and one to Orlando. I imagine someone thought it would be better to fly the available plane to Myrtle Beach and back and then go to Orlando since that round-trip was shorter. This didn’t account for the human factor of an end-of-week Orlando flight being 85% Disney passengers and putting the flight on a six-hour delay in New Haven airport… which, if you’ve been there, is tiny and has nothing to do for 50 kids excited to get to Disney. This delay was announced at the time of departure. No one realized before the time of departure there was no plane on the ground? And no one thought… hey I think the Myrtle Beach crowd might be a better one to have wait if we’re going to make a choice here (mind you the initial inbound plane was coming from Orlando and supposed to be out aircraft… they literally said let just grab this plane because it’s here to get this other group out at the last second). There is/was zero customer service desk for Avelo in HVN and there were no updates/announcements throughout the day. Plane still gets back late and we finally leave. No wi-fi on these planes, no snack or even water. I know this is budget airline, but expected at least a water after 8 hours of travel day. This should have been offered in terminal too. We land… hooray. Would you believe there is no ground crew to get the plane in to the gate… for 27 minutes. 27 minutes!!! At this point the rental car center is closing in 10 minutes, kids on the plane are crying again, and everyone is talking about how they’re never flying Avelo again. Finally get off. Bags are out at baggage claim right away (finally something right?), but they’ve stopped the carousel immediately and there is no baggage service rep. People are climbing over the carousel to get to the far side (if you’ve ever been to MCO you’ve seen it) because obviously they just stopped it immediately once all the bags were out. This airline is a dumpster fire. Icing on the cake was that while everyone was stuck in HVN, they were setting up for a celebration of their millionth passenger tomorrow. I bet 995,000 of those will never fly the airline again. Don’t fly Avelo. You’ve been warned.

Airline was the only available airline during the Southwest cancellation. It was easy to book. Lowest available fair. Convenient airports. Everything was great. Problem was, they didn’t release what gate flight was departing. The woman at the ticket booth didn’t know which terminal they were boarding and wanted me to wait in 30+ minute line versus telling me to look for flight kiosk. Burbank gate was packed. Otherwise the flight was perfect!!

The gate was too far away for the connecting flight

They switched out gate from terminal 1 to terminal two ten minutes before boarding. So we had to make a 20 min crazy fast walk to a different terminal. Then we boarded the plane and waited for over 40 minutes until push back. Brutal

Compared with other carriers business class for an overnight was not worth the extra expense.

Seats were comfortable. It’s was so cold and very uncomfortable. I paid 2000 miles for wifi service that was choppy the whole flight. Would like to be reimbursed for my miles Food was so disappointing. Three cold and terrible meals for $3000 round trip. This needs to be better.

Generally good. The aisles have gotten narrower which can slow down boarding. Flight crew was great! Healthier complimentary snacks would be appreciated. Due to earthquake in San Francisco we had to circle in air space for a bit but then had a smooth landing. I laud the flight crew for their patience ;)

Easy to board. Flight was super crowded though so I didn't sleep well on that cross country red-eye flight. The aisles seem ot have gotten narrower and the seat smaller whn luggage and people are getting bigger so it would be AWESOME to have more space and breathing room in general ;)

Excellent, professional, actually on time which is rare for late flights. Decent food. I love the new neck pillows! Nice, simple upgrade from the old ones I wasn't sure where to put. I wish they would allow more time for rest. It's a red eye 7 hour flight and meal service was about 3 hours.

We boarded but then sat there waiting on some missed connection people to get on so we sat for about 15 minutes for that. Then we sat again because the passenger manifest was wrong and they had to figure it out before we could leave. That took about another 20 minutes or so. The crew was working hard to figure it out so it’s not their fault. It ended up being a system glitch where someone was upgraded to first class while another person was also in the same seat and it just created a mess that took a little while to figure out. They literally went to every person on the plane asking their names to see who was sitting in the wrong seat. I also hate the entertainment that must be watched on your phone or tablet. Just give us setback screens. It’s so much better. Almost every Delta flight has this now and it is so nice to have them. The crew did a great job. I have no complaints from them. They were very hard working, even with the mishap and a disgruntled passenger.

We were delayed in Toronto on the tarmac for THREE hours with no clear indication as to why except that it was not a safety hazard. Pilot did apologize more than once but even he was unable to explain why exactly we were delayed. I overheard the stewards saying that the captain was very frustrated with the situation as well because he was not able to explain why except it had something to do with water supply or system on the aircraft and now we needed to wait for an engineer to approve the aircraft for flight. It was very frustrating and distressing as a passenger and we should have been given complimentary meals at the very least.

Flight was cramped with every seat taken. The food was fine, nothing crazy to write home about. The plane felt dated and needing some TLC, the button for the window shade didn't work and there were no AC outlets to use. When communicating with staff all except one nice lady never seemed happy to help me almost like I was bothering them when asked for things like a glass of water or a snack. The flight was overall fine. It did what was needed which is get me from point A to point B. But it certainly was not special. I don't expect much in economy but I believe economy on a host of other airlines is more memorable and better experience.

Except for the 28 minute delay leaving and the earlier reschedule to a later takeoff time the flight was good.

Loved the leg room and tvs screens on the seats and free WiFi. Wish the price was lower and could save by rebooking

No music app working: no economy meal on five hour flight; hour on tarmac at the end waiting for a gate. Flight itself was smooth and easy.

It took 1-1/2 hours to get our luggage after we landed. That to me is unacceptable

The flight was delayed for 4 hours. Once onboard the crew was wonderful.

Overall was excellent. Will definitely us JetBlue in the future.

Very well organized both boarding and deplaning. Very satisfied with the service I received.

I rate it is good we had a 4-hour travel delay at one point but JetBlue gave out food vouchers and travel points credits for another flight so they try to make up for it

Smooth boarding and friendly crew. Unfortunately as soon as we boarded the unit that provides air circulation failed. The pilot informed us and requested maintenance technicians to check it out. The plane became uncomfortably warm without any fresh air coming in. Plus the repair delayed our departure. I am glad the maintenance crew were able to fix the problem. I also was without use of my tv monitor for the first 1/3rd of the trip.

Flight was on time arrived at the destination 10min early they kept in touch via email

The trip was very smooth and they provided great customer service

The plane was late and then sat on the runway for almost 45 minutes before taking off.

Wonderful as usual except for other guests that were unruly and not kept in check by the Crew.

The flight was initially delayed, then cancelled. American Airlines says the cancellation was weather related, though the actual weather was not bad in both Washington and Providence and between. There were very few cancellations that day. In fact, AA2120 from Washington, DC to Boston flew with a minor delay at about the same time. So, the weather somehow affected only this particular flight AA5230. The next available flight was the following morning. The American Airlines refused to reimburse accommodation (hotel at DCA)

I have long legs, my foot was out in the aisle and when a flight attendant came walking by and I didn't notice, instead of saying "excuse me" or anything like that, she kicked my foot. Extremely rude

One bottle of water and a package of cookies for comfort plus. We had to literally beg a flight attendant for an extra bottle of water later in the flight due to feeling dehydrated.

Fine. On time, cabin service was fine, bag arrived. All good. Flying into DCA so did not collide with any helicopters, which is also good. Horrid incident that could have and should have been prevented.

Cabin was roomy enough to easily slide my carry on under the seat in front of me!

Everything was fine. Flight boarded and departed on time. Seating was spacious enough for my carryon to fit under the seat in front of me. No complaints at all. Flight even arrived early.

We kept being told that the flight was full and that all overhead compartments were full and therefore had to check in our hand luggage. We were some of the last people to board and noticed that there was still sufficient space in the overhead compartments. We were obliged to check in hand luggage when there was space and so had to wait at luggage retrieval which took a while to then noticed damage to our luggage - not a great experience!

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