$121 Find Cheap Flights from Hartford to Caribbean Islands - Compare and Save

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 8/20. 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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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$372
Santo Domingo
Santo Domingo1 stop$436
Montego Bay
Montego Bay1 stop$412
Oranjestad
Oranjestad1 stop$411
Nassau
Nassau1 stop$398
Kingston
Kingston1 stop$456
Simpson Bay
Simpson Bay1 stop$383
Providenciales
Providenciales1 stop$550
Port of Spain
Port of Spain2 stops$358
Bridgetown
Bridgetown1 stop$424
George Town
George Town1 stop$357
Willemstad
Willemstad1 stop$371
Aguadilla
Aguadilla1 stop$299
St. John's
St. John's1 stop$530
Puerto Plata
Puerto Plata1 stop$586
Punta Cana
Punta Cana1 stop$372
Santo Domingo
Santo Domingo1 stop$436
Montego Bay
Montego Bay1 stop$412
Oranjestad
Oranjestad1 stop$411
Nassau
Nassau1 stop$398
Kingston
Kingston1 stop$456
Simpson Bay
Simpson Bay1 stop$383
Providenciales
Providenciales1 stop$550
Port of Spain
Port of Spain2 stops$358
Bridgetown
Bridgetown1 stop$424
George Town
George Town1 stop$357
Willemstad
Willemstad1 stop$371
Aguadilla
Aguadilla1 stop$299
St. John's
St. John's1 stop$530
Puerto Plata
Puerto Plata1 stop$586

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

Wed, Oct 7 - Wed, Nov 4
Frontier Logo
9:25 pm - 1:10 amBDL  Hartford Bradley Intl-SJU San Juan Luis Munoz Marin Intl
3h 45mnonstop
Frontier Logo
9:30 am - 12:43 pmSJU  San Juan Luis Munoz Marin Intl-BDL Hartford Bradley Intl
4h 13mnonstop
$231Frontier
Mon, Oct 5 - Mon, Oct 26
Frontier Logo
9:25 pm - 1:10 amBDL  Hartford Bradley Intl-SJU San Juan Luis Munoz Marin Intl
3h 45mnonstop
Frontier Logo
8:30 am - 12:43 pmSJU  San Juan Luis Munoz Marin Intl-BDL Hartford Bradley Intl
4h 13mnonstop
$231Frontier
Wed, Sep 2 - Sun, Sep 6
Multiple Airlines Logo
1:42 pm - 5:46 pmBDL  Hartford Bradley Intl-SJU San Juan Luis Munoz Marin Intl
4h 04mnonstop
Multiple Airlines Logo
9:42 am - 4:14 pmSJU  San Juan Luis Munoz Marin Intl-BDL Hartford Bradley Intl
6h 32m1 stop Fort Lauderdale
$234Multiple Airlines
Sun, Aug 30 - Sat, Sep 5
Multiple Airlines Logo
1:42 pm - 5:46 pmBDL  Hartford Bradley Intl-SJU San Juan Luis Munoz Marin Intl
4h 04mnonstop
Multiple Airlines Logo
2:06 pm - 10:59 pmSJU  San Juan Luis Munoz Marin Intl-BDL Hartford Bradley Intl
8h 53m1 stop Orlando
$234Multiple Airlines
Tue, Sep 22 - Wed, Sep 23
United Airlines Logo
6:00 am - 8:38 pmBDL  Hartford Bradley Intl-SJU San Juan Luis Munoz Marin Intl
14h 38m2 stops Chicago O'Hare Intl Houston George Bush Intcntl
United Airlines Logo
1:00 am - 9:37 amSJU  San Juan Luis Munoz Marin Intl-BDL Hartford Bradley Intl
8h 37m2 stops Newark Washington, D.C. Dulles Intl
$237United Airlines
Wed, Sep 2 - Thu, Sep 3
United Airlines Logo
6:00 am - 12:54 pmBDL  Hartford Bradley Intl-SJU San Juan Luis Munoz Marin Intl
6h 54m1 stop Washington, D.C. Dulles Intl
United Airlines Logo
4:55 pm - 11:59 pmSJU  San Juan Luis Munoz Marin Intl-BDL Hartford Bradley Intl
7h 04m1 stop Washington, D.C. Dulles Intl
$238United Airlines
Tue, Sep 1 - Fri, Sep 18
Southwest Logo
3:30 pm - 10:00 pmBDL  Hartford Bradley Intl-SJU San Juan Luis Munoz Marin Intl
6h 30m1 stop Orlando
Southwest Logo
3:20 pm - 10:15 pmSJU  San Juan Luis Munoz Marin Intl-BDL Hartford Bradley Intl
6h 55m1 stop Baltimore/Washington
$240Southwest
Sun, Sep 13 - Tue, Sep 15
Southwest Logo
12:00 pm - 11:55 pmBDL  Hartford Bradley Intl-SJU San Juan Luis Munoz Marin Intl
11h 55m1 stop Baltimore/Washington
Southwest Logo
2:25 pm - 9:15 pmSJU  San Juan Luis Munoz Marin Intl-BDL Hartford Bradley Intl
6h 50m1 stop Baltimore/Washington
$240Southwest
Mon, Aug 31 - Thu, Sep 3
American Airlines Logo
5:02 am - 2:51 pmBDL  Hartford Bradley Intl-SJU San Juan Luis Munoz Marin Intl
9h 49m2 stops Washington, D.C. Reagan-National Charlotte Douglas
American Airlines Logo
1:38 pm - 11:47 pmSJU  San Juan Luis Munoz Marin Intl-BDL Hartford Bradley Intl
10h 09m1 stop Miami
$241American Airlines
Mon, Aug 31 - Thu, Sep 3
American Airlines Logo
5:02 am - 4:11 pmBDL  Hartford Bradley Intl-SJU San Juan Luis Munoz Marin Intl
11h 09m2 stops Washington, D.C. Reagan-National Miami
American Airlines Logo
2:33 pm - 11:51 pmSJU  San Juan Luis Munoz Marin Intl-BDL Hartford Bradley Intl
9h 18m2 stops Philadelphia Washington, D.C. Reagan-National
$241American 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 5 days was to Punta Cana, at $216 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 5 days was $226.

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 $342 on average. Morning departures are around 12% 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 $404.

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 $382, 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 $477 (return) on average. On the other hand, the most expensive months are July and June, when the average cost of round-trip tickets is $624 and $614 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 Friday. On your return trip to Hartford, you should consider flying back on a Friday, and avoid Sundays 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

Cheapest flight

$121
Best time to beat the crowds with an average 11% drop in price.
Most popular time to fly with an average 14% 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 $171 one-way - $305 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.
8.0
SouthwestOverall score based on 4218 reviews
7.5Entertainment
7.0Food
8.1Boarding
8.6Crew
8.0Comfort
Airline reviews

Exceptional. The gate crew responded quickly and got me onto this earlier flight as the final passenger, saving me more than four hours of wait time for my reserved flight.

10.0 ExcellentAnonymous, Aug 2026
Read more Southwest reviews

Exceptional. The gate crew responded quickly and got me onto this earlier flight as the final passenger, saving me more than four hours of wait time for my reserved flight.

The flight was delayed due to earlier issues at other airports. The crew was excellent & made it a good trip.

The flight was smooth. The Southwest experience has degraded overall, but this one was okay.

The last 3 flights between BWI and BDL canceled the beverage service mid- way. Just say up front that the fight is too short. Thanks!

It was okay. The plane was delayed from earlier in the day, but they kept updating the departure time, sometimes later, sometimes earlier. That was stressful. Once we finally got on and took off, it was fine. I was supposed to have a connection in Chicago to Los Angeles, and the time for so late I was rebooked to arrive in LA 3 hours late. The departure time to Chicago later became early enough to have taken my original connection and arrive earlier but that wasn't an option.

It was fine. For some reason the flight was much longer than usual. It may have been explained, but I had noise cancelling earbuds on and missed a couple of announcements. The crew was fine, but there was a flight attendant who kept telling dumb jokes, occasionally one I found distasteful. This was my second time with him, but luckily it was a late flight so he didn't do as many. But I heard all of today's jokes twice, which was two times too many. Good takeout and landing.

Boarding good… although I wish SW had another seating system. We had to rush the beverages as the flight was only 50 minutes. It seemed to take forever for my husband to get the wine he ordered, and my coffee. We were then told to drink it like we were in collage, as landing was soon…..

Paid for early bird. Basically paid for nothing. Would have been in the same spot regardless since the entire plane family preboarded between A and B. If they can’t give you A they should be required to refund the early bird fee. Also I don’t know what the issue is with the flight attendants but their attitudes need to change.

Would have liked screens on the back of each seat.

The boarding process of Southwest and the “first come first serve” seat selection is very difficult and prolongs the actual boarding process as people figure out where to sit.

the flight got cancelled - few hours before the departure time - no time to change

This a short easy flight. No food or drink but that was not an issue since we were only in the air for 35 minutes.

The meal tray was not usable it was completely uneven

My experience with Delta started with my luggage being found ripped open with items missing. The baggage office told me to bring the bag, and I wanted them to see how I found it. The agent refused, so I carried my bag into the office myself. The agent was nice enough to fix the zipper and gave me a red card with a number to call. I followed the steps; first one department, then the baggage department took over. This took more than two hours on the phone. The return flight was okay. The flight lead was checking her meals and then asked if we wanted anything before departure. However, throughout the flight, I had to ask for things because she was reading her book;which I have no issue with if she had been more attentive. At the end of the flight, the pilot appeared annoyed with the flight lead for not following his instructions regarding a meal he had requested; a chicken sandwichand said, "I asked for that for the flight." On the positive side, my work event in Vegas went well, and now I'm home relaxing.

Internet connectivity still seems to be touchy on these flights, making it difficult to rely on it for getting work done.

The ac must have died, it was way to hot on this flight. Boarding g was chaotic. The flight was delayed for boarding. Not a great experience.

Comfortable seats. Nice service online. Short flight, so not a lot of time to enjoy.

Awful. There was an unexpected delay of nearly three hours because there were not enough flight attendants. I understand this is likely due to FAA regulations; but in that case, Delta should coordinate with smaller airports such as RDU to have extra flight attendants on the ground and "on call". In addition, this was the second 2-hour+ delay to Boston on this route in one week.

Everything was good except when we're on a 6 hour flight at dinner time and all they offer as part of the fare are little bags of junk food, it's disappointing. Bring back food service without an added price.

It's OK. Engine was noisy. The flight was super late. I mean 4 hours late. That is unheard of.

It was a good experience, unfortunately my checked baggages were come late and not arrived on time.

Very stressful to locate United Airline boarding area, delayed flight, changing boarding area again to another location with all tiredness 😩. But flying was fine.

Staff and flight attendants were very polite. Flight was smooth. My seat on the plane was a bit broken so it would not stay in upright position but it was fine for the most part.

Flight staff and all was fine. Food always sucks on planes so nothing new.

The flight crew were very helpful. The seats were very close together. There was barely room to sit without touching the person next to you.

I’m an EP on AA every year for more than a decade but this was a very pleasant and surprising experience. Clean and sizable plane for HOU to CHI. 5 row first class. And excellent food in first class the steak option was really good. Your flight attendants even better. Seat 5A

It was hot and not as comfortable as the flight to Chicago. Must have been a different plane that needs to be worked on or replaced.

Overall a good experience, but no wifi available for free or for purchase and we got wet from condensation or other water source during descent.

Plane didn’t even make it off the ground. We all had to get off and walk to a different terminal (lots of confusion) to get on a different plane. Landed fairly late, connections missed.

Awful…flight was delayed more than 12hrs, missed all connections to Fort Wayne, IN, had to get flight to another city 2 hours from my destination, flight was again delayed by 40 mins because they did not have enough fuel, again missed a connection, finally arrived in Indiana at 11pm…but before my 2 hour drive home, ay, no Five That Our Luggage Never Made On The plane and Still In Chicago

The power outlets were not working for my row. Also felt like the seats have gotten smaller. I was in the window seat and felt like suffocated, as the two passengers next to me were tall and wide.

Delays and multiple changes in gates. In accurate info sent to phone. Worst flight in years. With no apologies or recompense.

No AC, no beverage service and no explanation from the captain. 4 flight legs in 2 days with no internet service.

No service on New Orleans to DFW or DFW to San Antonio. Also no explanation from the captain why we had no AC. Unacceptable!

the first flight smelled like urine Ac didn’t work pathetic experience

The flight was delayed multiple times. I was autobooted and placed in the center seat in the last row of the plane.

Am still mad at American airlines. You should know it's us travel nurses who are your customers and you treat us like nonsense it's not ok. American airlines took my money, no refund for whatsoever. A trip that was of 466 and I paid 466 and 833 then they chose for me where to sit and refund my seat choices and gave me expensive seats for 79 USD. Kayak doesn't help at all after booking you are on your own. Skyscanner is better

Terrible experience with baggage claim at CLT. Posted as arriving at belt 4 and screen there showed the flight. Waited for over 1.2hrs before someone randomly came by and said the bags for that flight had been dropped at CD1 an unknown time ago. There was no notification in the app, on the screens or by any airport personnel prior to this time. Waiting 1.2 hrs after a 2 hr flight for a bag you paid $40 extra to check is infuriating and disappointing.

On the new 319 NEO? seatback entertainment system did not work even when the flight attendant rebooted it. At least I had my cell phone to connect with wifi.

Delay. Flight was delayed in Washington.knew that connection was impossible as not enough time to switch terminals. The steward would not let me stay the night. So forced to Dallas.late night, after 10pm.hotel checkin was one hour. Passengers lined up only one girl to checkin at comfort inn. No food availability at that time. Had to leave early at 6:30 am to catch a flight at 8:45. Stressfull.

A more comfortable seat. Padding would be really helpful but I've read the airlines don't want customers to be satisfied with economy seats.

When I booked, I included my checked luggage and when the bill was sent there was no record of this. Its was costly since I am from Trinidad amd Tobago. Exchange rate over seven dollars to one US dollar.

Everything was good except checking bags . I had paid for two bags but it didn’t show so we had to do it again while people waited and we were struggling to get to our flight

Flight delayed 4 times on a non-stop from BOS to SFO. Then when landed in SFO had to wait for 30 mins for a gate AT 3:30AM.

Plane was delayed multiple times. I would like to request a refund. Was due to arrive Thursday evening ended up arriving Friday morning.

The seats were roomier than other airplanes I’ve been on.

The crew and the pilots. The pilots were amazing. The landing in Cancun was excellent.

The security line at JFK was one of the longest I’ve ever experienced - probably 45 minutes. I don’t know if JetBlue has control over it, but it detracted from the overall experience. Entertainment had good options, but the volume control was a bit small to tap on and the screen had a fair amount of interference blips. Clearer picture would have been better.

Like the variety of entertainment options. One crew member was a little on the rough/rude side. Boarding was a mess, attendants didn't do a great job of helping with the luggage storage and it delayed us a couple of minutes.

The flight was delayed after already taxiing from the gate due to a malfunction. After 3 hours we were told the flight was canceled. The next flight available was Sunday. My daughter and I stayed overnight in the airport due to this issue. I was given a $12 meal voucher. Unacceptable

Everything you need to know for your flight to Caribbean Islands

Information on your arrival and departure airports