$92 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 5/26. 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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Flight Deals

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$322
Santo Domingo
Santo Domingo1 stop$371
Montego Bay
Montego Bay1 stop$348
Oranjestad
Oranjestad1 stop$350
Nassau
Nassau1 stop$340
Kingston
Kingston2 stops$421
Simpson Bay
Simpson Bay2 stops$338
Providenciales
Providenciales1 stop$536
Port of Spain
Port of Spain2 stops$316
Bridgetown
Bridgetown1 stop$374
George Town
George Town1 stop$321
Willemstad
Willemstad2 stops$325
Aguadilla
Aguadilla1 stop$258
Puerto Plata
Puerto Plata1 stop$602
St. John's
St. John's1 stop$672
Punta Cana
Punta Cana1 stop$322
Santo Domingo
Santo Domingo1 stop$371
Montego Bay
Montego Bay1 stop$348
Oranjestad
Oranjestad1 stop$350
Nassau
Nassau1 stop$340
Kingston
Kingston2 stops$421
Simpson Bay
Simpson Bay2 stops$338
Providenciales
Providenciales1 stop$536
Port of Spain
Port of Spain2 stops$316
Bridgetown
Bridgetown1 stop$374
George Town
George Town1 stop$321
Willemstad
Willemstad2 stops$325
Aguadilla
Aguadilla1 stop$258
Puerto Plata
Puerto Plata1 stop$602
St. John's
St. John's1 stop$672

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

Sun, May 24 - Fri, May 29
Frontier Logo
1:48 pm - 5:52 pm
BDL
-
SJU
4h 04mnonstop
Frontier Logo
8:33 am - 12:44 pm
SJU
-
BDL
4h 11mnonstop
$172Frontier
Sun, May 24 - Sun, Jun 7
Frontier Logo
1:48 pm - 5:52 pm
BDL
-
SJU
4h 04mnonstop
Frontier Logo
8:33 am - 12:44 pm
SJU
-
BDL
4h 11mnonstop
$174Frontier
Wed, Sep 2 - Thu, Sep 3
American Airlines Logo
7:24 pm - 12:52 pm
BDL
-
STT
17h 28m
2 stops
American Airlines Logo
4:42 pm - 11:52 pm
STT
-
BDL
7h 10m
1 stop
$285American Airlines
Thu, Jul 30 - Tue, Aug 4
American Airlines Logo
6:01 am - 1:48 pm
BDL
-
STT
7h 47m
1 stop
American Airlines Logo
2:41 pm - 10:23 am
STT
-
BDL
19h 42m
2 stops
$317American Airlines
Tue, Jul 7 - Thu, Jul 9
JetBlue Logo
7:00 am - 2:19 pm
BDL
-
PUJ
7h 19m
1 stop
JetBlue Logo
11:56 am - 11:56 pm
PUJ
-
BDL
12h 00m
1 stop
$322JetBlue
Tue, Sep 1 - Fri, Sep 4
JetBlue Logo
8:00 am - 5:33 pm
BDL
-
MBJ
10h 33m
1 stop
JetBlue Logo
3:27 pm - 11:56 pm
MBJ
-
BDL
7h 29m
1 stop
$348JetBlue
Mon, Aug 24 - Wed, Aug 26
Delta Logo
7:00 am - 2:39 pm
BDL
-
PUJ
7h 39m
1 stop
Delta Logo
2:50 pm - 11:58 pm
PUJ
-
BDL
9h 08m
1 stop
$352Delta
Tue, Jun 2 - Fri, Jun 12
United Airlines Logo
6:00 am - 3:10 pm
BDL
-
MBJ
10h 10m
1 stop
United Airlines Logo
4:12 pm - 11:59 pm
MBJ
-
BDL
6h 47m
1 stop
$352United Airlines
Tue, Jul 28 - Wed, Jul 29
United Airlines Logo
6:09 am - 3:10 pm
BDL
-
MBJ
10h 01m
2 stops
United Airlines Logo
4:12 pm - 11:59 pm
MBJ
-
BDL
6h 47m
1 stop
$369United Airlines
Tue, Jul 7 - Thu, Jul 23
Delta Logo
7:00 am - 3:34 pm
BDL
-
MBJ
9h 34m
1 stop
Delta Logo
1:17 pm - 11:54 pm
MBJ
-
BDL
9h 37m
1 stop
$398Delta
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 $124 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 $124.

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 afternoon, when round-trip flights cost $322 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 $384.

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 $366, 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 June, when tickets cost $114 (return) on average. On the other hand, the most expensive months are December and April, when the average cost of round-trip tickets is $800 and $656 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 1 week before departure. For the absolute cheapest price, our data suggests you should book 5 weeks before departure.

Good to know

Low seasonSeptember
Cheapest flight$92
Best time to beat the crowds with an average 14% drop in price.
Most popular time to fly with an average 12% 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 $149 one-way - $245 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 8455 reviews
7.8Comfort
8.1Boarding
8.5Crew
7.2Food
7.8Entertainment
Airline reviews

For some reason, TSA Atlanta didn’t have my bag on the flight on time and they don’t have to provide Delta a reason for that.

6.0 GoodRafiq, May 2026
ATL - GSP
Read more Delta reviews

For some reason, TSA Atlanta didn’t have my bag on the flight on time and they don’t have to provide Delta a reason for that.

WiFi didn’t work on two of four planes. Flight attendants were not overly friendly or welcoming. Planes were extremely slow to board and deplane.

Delta does a great job with entertainment and free wifi. I can still be in touch with my colleagues while in the air.

Aside from a completely packed plane, I really have no complaints.

Bus to plane was delayed for no apparent reason and our luggage was still on the belt when they shut it off. Took about 20 minutes to turn it back on to get our luggage.

It was a pleasant surprise to have complimentary Wi-Fi on the flight

Much better than Latam, the worse airline company ever. I hope I don't have the need to fly Latam ever in my life again.

Seats in Delta Main are unbelievably close to the seat in front of. Hard to get a backpack under the seat.

The flight was operated by Latam. The aircraft had a technical issue and the flight was delayed for the next day. They grounded other passengers to get their airplane assigned to my flight. Most of he ground staff don't speak English (Orlando Airport), but were very polite.The crew on the other hand could speak English and Portuguese. On board service was good.

The agent at check in and at the gate were less than thrilled to be at work. I'm not a fan of Kayak's placement on the plane. I got put in the middle seat and none of my preferences were used.

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.

Excellent! I got to Munich and was transferred to my Lufthansa flight quickly, in 15 to 20 minutes, so I did not miss my flight. However, I had checked my overhead bag at the boarding gate in Tampa. That got to Tunis the next day. That is to be expected.

It's a short hop. My carryon was checked at the gate, I didn't have to drag it all over the airport. Excellent wheelchair assist.

WiFi didn’t exist , seats were super cramped, lights stayed on near my seat for a long time while others were dimmed, the food/trash/drink cart hit my shoulder at least a couple of times while moving, food options were down to just one option by the time it got to my row, the utensils were garbage (knife bent at a couple of places by the time I was done eating) the spoon was very flimsy plastic

Friendliest Flight Attendant I’ve seen since I flew on Southwest Airlines. The whole trip was outstanding…and arrived Early!

It was good overall except from Omaha to Denver when flight a was a repeatedly delayed apparently due to some issue at Denver. Communications could have been handled better. I had to board then deboard with luggage and board again

I didn’t have a seat assignment and my seat was very dirty on the flight from Frankfurt to Budapest.

Left an hour and a half after the listed time. Up side was it had TV screens on the seat.

No screens or meal options. Freezing cold. Dirty seats. Left late.

O’hsre taxi and deboarding took 40 minutes. Needed 20 minutes extra time between connecting flights to avoid running through terminal.

Cree was organized and pleasant. Plane had good seating but as it’s a shuttle toilets hadn’t been thoroughly cleaned (eg. bins too full)

JetBlue not only has the most comfortable planes, but also used to have the best customer service. Lorie Wright, the lady at the gate was very rude not only to me, but to other passengers as well. Her colleague, the gentleman was also not very friendly. They both were acting like they were doing passengers a favor. The crew on board was very nice.

Flight was on time and smooth. Customer service was decent

The space between seat rows seemed to be larger than other airlines. I didn’t check their food or entertainment since I slept most of the way. They do seem to have a lot of options for purchase though.

Kayak sucked. You gave me a confirmation number that was not useable by the jet blue system. Nor did you send any check in emails. I’ll not be using your site again. Nice work.

Direct tv did not work on flight Short flight so no good service offered Arrived early to destination and had to wait for gate to open. Deplaned LATER than if we arrived on time!! Poor planning Jet blue has had something go wrong on every flight I’ve taken with them in last five years. Terribly run airline

Given us a free miles or free flight for waiting for 9 hours I didn’t get home till 5am in the morning and I was supposed to be home at 9:30 touch down.

Excellent price. Everything on time. two bad parts. Kayak said I couldn't sign in for the flight online, but I got an email at the same time from Jet Blue and they let me sign in online. Second bad part was that, although I had provided my known traveler number, neither of my boarding passes, for this flight and the previous one, had TSA pre-check showing.

Jet blue was great But the Jayak system Wasa pure nightmare and wasted so much of my time and energy by not giving me a way to access jet blue to check in the flight back I didn’t even get the number confirmation code 24 hours before. Because I didn’t receive the email with the confirmation code I could NoT CHECk IN. I spoke to a kayak third party and they informed me I could not carry a carry on, on the flight which caused me so much extra stress it was just too much. You can be sure I will not be using it recommending your site. Again.

There was a screen but no earphones that could use the older input so I could listen to anything.

My experience with JetBlue was fine BUT I am very upset with Kayak! JetBlue had delayed our scheduled departure by an hour and you NEVER notified me of the change. I did not hear directly from JetBlue because the trip was booked through Kayak, a mistake I will not repeat. Your reminder of the our trip last week still had the WRONG departure time. Our return trip has also changed, and again no notice from you.

Seat comfort was poor (no lumbar or lower back support).

The airplane seats were spacious and comfortable, and the flight attendants were friendly and attentive. The food was delicious like never before. The blankets and toiletries were thoughtfully provided. The captain's navigation was steady and reliable. In short, having flown with Starlux, I won't consider any other airline next time.

STOP MAKING THE SEATING SO CRAMPED. WE NEED A PASSENGER BILL OF RIGHTS!

The passenger in front of of me reclined their seat back all the way the entire flight. Their headrest was in my face the entire flight! I barely had room for the little plastic cup of water to fit on my tray table; can you make the seats and space between the rows any smaller??? You can’t even get up to use the restroom! Worst flight I’ve had in a very long time!

We had several flights and they were all on-time and flawless

My Frequent Flyer nber wasn't put on as I was told it was..... This resulted in a last group boarding and no priority tags on My bags.

Premium Economy Good crew, good service, excellent food. Seat back screen just not bright enough.

Terrible steward... Plane was quite empty... I asked to move "back" in the plane and the steward said no... Unnecessary power trip of mediocre people.

Flight was delayed an no one cares, or try to help passengers to get the conexión.

Our flight was cancelled while we are on our way to the airport. So, no notice. We were rescheduled to another airline with a 2 hour later takeoff and so arrived at our destination on time. We pre-paid American Airlines $190 to upgrade our seats. No refund. So no use for AA or Kayak.

Everything you need to know for your flight to Caribbean Islands

Information on your arrival and departure airports