$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 8/16. 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$373
Santo Domingo
Santo Domingo1 stop$426
Montego Bay
Montego Bay2 stops$402
Oranjestad
Oranjestad2 stops$416
Nassau
Nassau1 stop$398
Kingston
Kingston1 stop$456
Simpson Bay
Simpson Bay1 stop$383
Providenciales
Providenciales1 stop$533
Port of Spain
Port of Spain2 stops$356
Bridgetown
Bridgetown2 stops$419
George Town
George Town1 stop$357
Willemstad
Willemstad2 stops$365
Aguadilla
Aguadilla1 stop$296
St. John's
St. John's1 stop$530
Puerto Plata
Puerto Plata1 stop$581
Punta Cana
Punta Cana1 stop$373
Santo Domingo
Santo Domingo1 stop$426
Montego Bay
Montego Bay2 stops$402
Oranjestad
Oranjestad2 stops$416
Nassau
Nassau1 stop$398
Kingston
Kingston1 stop$456
Simpson Bay
Simpson Bay1 stop$383
Providenciales
Providenciales1 stop$533
Port of Spain
Port of Spain2 stops$356
Bridgetown
Bridgetown2 stops$419
George Town
George Town1 stop$357
Willemstad
Willemstad2 stops$365
Aguadilla
Aguadilla1 stop$296
St. John's
St. John's1 stop$530
Puerto Plata
Puerto Plata1 stop$581

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

Fri, Nov 6 - Mon, Nov 9
Frontier Logo
1:38 pm - 6:38 pm
BDL
-
SJU
4h 00mnonstop
Frontier Logo
9:30 am - 12:43 pm
SJU
-
BDL
4h 13mnonstop
$241Frontier
Wed, Sep 9 - Wed, Sep 16
Multiple Airlines Logo
9:25 pm - 1:10 am
BDL
-
SJU
3h 45mnonstop
Multiple Airlines Logo
4:39 pm - 11:36 pm
SJU
-
BDL
30h 57m
2 stops
$241Multiple Airlines
Tue, Sep 22 - Tue, Sep 29
United Airlines Logo
6:00 am - 8:38 pm
BDL
-
SJU
14h 38m
2 stops
United Airlines Logo
1:00 am - 2:29 pm
SJU
-
BDL
13h 29m
2 stops
$242United Airlines
Tue, Sep 22 - Wed, Sep 30
United Airlines Logo
6:00 am - 8:38 pm
BDL
-
SJU
14h 38m
2 stops
United Airlines Logo
4:55 pm - 11:59 pm
SJU
-
BDL
7h 04m
1 stop
$242United Airlines
Tue, Sep 1 - Thu, Sep 10
Southwest Logo
3:30 pm - 10:00 pm
BDL
-
SJU
6h 30m
1 stop
Southwest Logo
3:20 pm - 10:15 pm
SJU
-
BDL
6h 55m
1 stop
$242Southwest
Tue, Sep 1 - Wed, Sep 9
Southwest Logo
3:30 pm - 10:00 pm
BDL
-
SJU
6h 30m
1 stop
Southwest Logo
2:25 pm - 9:15 pm
SJU
-
BDL
6h 50m
1 stop
$242Southwest
Fri, Aug 21 - Tue, Aug 25
Frontier Logo
1:42 pm - 5:46 pm
BDL
-
SJU
4h 04mnonstop
Frontier Logo
8:57 pm - 11:32 am
SJU
-
BDL
14h 35m
1 stop
$242Frontier
Fri, Oct 9 - Tue, Oct 13
Multiple Airlines Logo
1:38 pm - 5:38 pm
BDL
-
SJU
4h 00mnonstop
Multiple Airlines Logo
7:00 am - 10:56 am
SJU
-
BDL
3h 56mnonstop
$243Multiple Airlines
Fri, Aug 28 - Tue, Sep 1
American Airlines Logo
11:04 am - 9:55 pm
BDL
-
SJU
10h 51m
2 stops
American Airlines Logo
6:00 am - 11:47 pm
SJU
-
BDL
17h 47m
1 stop
$251American Airlines
Fri, Aug 28 - Tue, Sep 1
American Airlines Logo
11:10 am - 11:59 pm
BDL
-
SJU
12h 49m
1 stop
American Airlines Logo
6:00 am - 11:47 pm
SJU
-
BDL
17h 47m
1 stop
$251American 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 $246.

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 $343 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 $402.

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 $386, 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 $473 (return) on average. On the other hand, the most expensive months are July and June, when the average cost of round-trip tickets is $617 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 15% 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 $181 one-way - $312 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 4226 reviews
7.0Food
8.1Boarding
8.0Comfort
7.5Entertainment
8.6Crew
Airline reviews

Eveeyrime I fly they are begging for bags due to cabin overhead space. What they should so ia take the bags that are clearly too big to fit wheels first on their side. And those of us who give up the bag should really get their bags first. When boarding, nobody wants stupid jokes about how hot it is on board. Give us some cool air. Im usually sick from the heat by the time we take off.

6.0 GoodVera, Jul 2026
MCO - BNA
Read more Southwest reviews

Eveeyrime I fly they are begging for bags due to cabin overhead space. What they should so ia take the bags that are clearly too big to fit wheels first on their side. And those of us who give up the bag should really get their bags first. When boarding, nobody wants stupid jokes about how hot it is on board. Give us some cool air. Im usually sick from the heat by the time we take off.

No wifi, seems to be very common with Southwest currently. Everything else was normal.

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.

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.

It was strange that the flight attendant was so adamant about having phones turned to airplane mode that he was calling out names from networks shown and waiting until they were all gone. I've never experienced that before, and after already working through an hour+ delay, it felt tone deaf. I take dozens of flights per year and have never experienced anything similar.

The flight was done by SkyWest only WIFI no entertainment center are available on the CRJ

Your survey needs a N/A option. I didn’t use the entertainment or eat food.

The flight was over 2 hours late.. once we finally got boarded things were fine

Poor communication, we sat on the plane for an hour before pushing back. They were oversold and with a full plane kept looking for someone to step off for someone else to board. So after an hour wait at the gate we missed our departure window and proceeded to spend an additional hour on the tarmac waiting for a refiled flight plan according to the pilots. Occasional updates, somewhat insensitive crew to passengers needing to use the lavatory (it was 2 hrs beyond what anyone expected). Overall just poor execution...especially when the flight was listed as "arriving early" up until about 30 minutes past our departure time.

No tv. No free wifi. They need to ipgrade these planes - especially on a 2 hour flight.

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.

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.

My flight was delayed so bad i missed u it so i just said never mind

Wonderful flight! The crew was good, check-in was good and orderly and the flight was uneventful and good.

Gluten free snack options and meals that offer both gluten free and dairy free.

The pilot was late so we didn’t take off til almost 2 hours late.

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

This flight 1810 on 7/30 from EWR to DFW got 4 hours delay. this round trip experience is bad, my AA flight 618 from DFW to EWR on 7/28 was redirected to PIT and totally delayed about 9 hours due to mixed of weather and AA IT outage and then on the way back delayed for 4 hours. Lucky, i changed my flight to UA on the way back. i don't like AA anymore. i will consider other airline options in the future.

Bad experience going to DFW with an IT outage then bad on the way back with a nearly 5 hour delay that’s started as maintenance then caused us to wait further due to weather - which would not have happened if we had left on time.

IT issues created a mess had you change my flight and your system never changed it

Horrible experience flying with American. Flight was delayed due to inbound flight delay. Fine, it happens. Then, we were delayed an additional almost 30 minutes due to the paperwork for departure having a "clerical error." Then, upon landing at the destination airport we were stuck on the plane for an HOUR after we landed and pulled up to the gate because apparently there was another plane. An hour waiting for the gate 12:30 AM when the flight has already been delayed due to operational error feels like a complete failure of the ability to do the one thing they need to do apart from actually have the plane takeoff and land. Very disappointing.

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.

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.

I liked the entertainment on JetBlue, the service from JFK to JAX was terrible at best

I usually dont fly JeTBlue and I dont think I will ever do it again. The flight was delayed fee time, nobody was giving us any info at at the airport, gate changing, the slowest and poorly organized boarding ever, rude staff.. huh

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