$122 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 7/21. 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$342
Santo Domingo
Santo Domingo1 stop$383
Montego Bay
Montego Bay2 stops$415
Oranjestad
Oranjestad1 stop$337
Nassau
Nassau1 stop$322
Kingston
Kingston1 stop$424
Simpson Bay
Simpson Bay1 stop$351
Providenciales
Providenciales1 stop$498
Port of Spain
Port of Spain2 stops$336
Bridgetown
Bridgetown1 stop$394
George Town
George Town1 stop$341
Willemstad
Willemstad2 stops$345
Aguadilla
Aguadilla1 stop$334
Puerto Plata
Puerto Plata1 stop$587
St. John's
St. John's1 stop$680
Punta Cana
Punta Cana1 stop$342
Santo Domingo
Santo Domingo1 stop$383
Montego Bay
Montego Bay2 stops$415
Oranjestad
Oranjestad1 stop$337
Nassau
Nassau1 stop$322
Kingston
Kingston1 stop$424
Simpson Bay
Simpson Bay1 stop$351
Providenciales
Providenciales1 stop$498
Port of Spain
Port of Spain2 stops$336
Bridgetown
Bridgetown1 stop$394
George Town
George Town1 stop$341
Willemstad
Willemstad2 stops$345
Aguadilla
Aguadilla1 stop$334
Puerto Plata
Puerto Plata1 stop$587
St. John's
St. John's1 stop$680

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, Aug 20 - Fri, Aug 28
American Airlines Logo
7:24 pm - 3:52 pm
BDL
-
STT
20h 28m
2 stops
American Airlines Logo
3:43 pm - 10:22 am
STT
-
BDL
18h 39m
2 stops
$206American Airlines
Mon, Jul 20 - Fri, Jul 24
Frontier Logo
1:42 pm - 5:46 pm
BDL
-
SJU
4h 04mnonstop
Frontier Logo
8:45 am - 12:47 pm
SJU
-
BDL
4h 02mnonstop
$248Frontier
Sat, Aug 22 - Wed, Aug 26
Delta Logo
6:00 am - 1:57 pm
BDL
-
NAS
7h 57m
1 stop
Delta Logo
1:16 pm - 8:53 pm
NAS
-
BDL
7h 37m
1 stop
$322Delta
Mon, Sep 14 - Thu, Sep 24
JetBlue Logo
7:00 am - 2:05 pm
BDL
-
AUA
7h 05m
1 stop
JetBlue Logo
3:25 pm - 11:14 pm
AUA
-
BDL
7h 49m
1 stop
$337JetBlue
Sat, Aug 29 - Sat, Sep 5
Delta Logo
5:30 am - 12:59 pm
BDL
-
PUJ
7h 29m
1 stop
Delta Logo
2:25 pm - 11:51 pm
PUJ
-
BDL
9h 26m
1 stop
$342Delta
Tue, Jul 21 - Thu, Jul 23
JetBlue Logo
8:00 am - 1:50 pm
BDL
-
NAS
5h 50m
1 stop
JetBlue Logo
2:51 pm - 10:58 pm
NAS
-
BDL
8h 07m
1 stop
$349JetBlue
Wed, Jul 8 - Sun, Jul 12
United Airlines Logo
8:20 am - 3:56 pm
BDL
-
NAS
7h 36m
1 stop
United Airlines Logo
3:59 pm - 10:21 am
NAS
-
BDL
18h 22m
1 stop
$368United Airlines
Tue, Sep 8 - Tue, Sep 15
United Airlines Logo
6:00 am - 12:40 pm
BDL
-
PUJ
6h 40m
1 stop
United Airlines Logo
4:40 pm - 9:37 am
PUJ
-
BDL
16h 57m
2 stops
$382United Airlines
Wed, Nov 11 - Wed, Nov 18
Southwest Logo
5:15 am - 2:20 pm
BDL
-
SXM
8h 05m
1 stop
Southwest Logo
3:20 pm - 8:00 am
SXM
-
BDL
17h 40m
2 stops
$403Southwest
Tue, Nov 3 - Tue, Nov 10
Southwest Logo
5:15 am - 1:45 pm
BDL
-
PLS
8h 30m
1 stop
Southwest Logo
2:40 pm - 8:00 am
PLS
-
BDL
17h 20m
2 stops
$498Southwest
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 $235.

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 $346 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 in the morning, which is peak travel time and where the average cost of a ticket is $392.

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 $392, 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 October, when tickets cost $120 (return) on average. On the other hand, the most expensive months are June and December, when the average cost of round-trip tickets is $1,111 and $791 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 Tuesday, 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 seasonSeptember
Cheapest flight$122
Best time to beat the crowds with an average 12% 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 $165 one-way - $340 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
SouthwestOverall score based on 4246 reviews
8.1Boarding
8.0Comfort
7.5Entertainment
8.6Crew
7.0Food
Airline reviews

SW can't get their wifi right. I upgrade to insure wifi service but the last two trips had intermittent service. Not worth the extra costs.

6.0 GoodAnonymous, Jun 2026
TPA - DAL
Read more Southwest reviews

SW can't get their wifi right. I upgrade to insure wifi service but the last two trips had intermittent service. Not worth the extra costs.

The flight was late. The crew was rude. There was no food. Cramped and uncomfortable. Nothing about this flight was good.

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.

It was as good as it could be. Flying is not a pleasant experience these days.

The plane was old and thus the seats were not good. No cushion left whatsoever, and it all was a bit worn out.

I was in Comfort and we didn’t get any drinks, chips or anything! First Class got full service on the flight and Comfort got nothing. Seat was horrible and uncomfortable

My flight was delayed by 4 hours in 30 minute increments. The gate agents were amazing but the communication was not. We were told that there was a maintenance issue but they didn't know what it was. That didn't inspire confidence. Then they said they found it and it was fixed and the pilot just needed to sign off. Then the pilot needed to talk to the other pilot from the arriving flight and we'd be fine. Then we were waiting for the pilot to call back. Then the maintenance issue wasn't fixed. Then they decided we were getting a new plane (why didn't they decide this earlier??). Fine. But then they announced we were changing gates AND terminals. And we were boarding in 20 minutes. So we all had to run to the new terminal gate. We could have taken off at that time, but we then had to wait for all the people who rebooked on a different flight to book this flight again. That took 30+ minutes because there was only one gate agent. When everyone ditched this flight, I saw it as an opportunity to upgrade to comfort. Delta, the greedy jerks they are, charged me $121. After their delay, their fault, their issues, couldn't even discount an upgrade. They only handed out $12 meal vouchers for the delay. I can't even get a snack from starbucks for that.

The crew was very inconsiderate and rude. My flight was scheduled to depart at 6:00am. I received a call from the crew at 5:40am, asking if I was going to make the flight because I was the only one that hasn't boarded yet and boarding ends at 5:50am. I let them know that I will be at the gate in a few minutes, before the 5:50am cutoff. When I arrived at the gate at 5:45am the gate was closed. Departing early on last minute notice without having all passengers on board is inconsiderate and unprofessional.

FA was a bit strange and dodgy not very characteristic of Delta

Not really a “Delta” problem but worth mentioning: Boarding was a difficult process. TSA seemed understaffed and Pre-Check took longer than regular TSA. The supervisor was frazzled and yelled at travelers. Once through TSA, we had to put our carry-ons through another x-ray machine. Then queue up to board with both boarding pass and ID. Then, when we got to the stairs on the tarmac, we had to show our boarding pass again. Maybe this is just normal for Kona since the terminal is outdoors (but still a “secured” area).

flight was delayed 4+ hours. there was really no understanding of why? weather? the last hour of delay was post boarding. pilot seat was broken. was that the real reason? nonetheless, long day of inconveniences.

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.

Great staff. Clean plane, but we were delayed for more than an hour due to maintenance issues and had to board another plane.

I was very disappointed with my experience at the United Airlines baggage check. The representative was rude and unhelpful. I was required to remove approximately 1.5 pounds from my two checked bags, even though it was a very small amount over the limit. The interaction was unnecessarily unpleasant, and I expected much better customer service. I hope United will review this incident and provide additional customer service training to its staff.

No extra snacks were available. Meals quality is terrible. Crew was not friendly.

I was exhausted from a long day. The flight was smooth. The first flight during my 3 week travel that took off on time.

Agents at gate were not immediately available to solve problems and once they did they didn’t fix all the fight connections

1 flight cancelled Had to fly out of different city Flight at new departure city was delayed 3 hours causing us to miss connecting flights. By the time we did make it to Prague our luggage did not. Had to wait day and a half for luggage to be delivered. Customer service was not good. Agents did not arrive at gate until 5-10 minutes before boarding

I needed internet for critical matters and it never worked.

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

I cancelled this flight 2 days before departure but I followed your texts and emails and IF you were correct this flight turned into a nightmare.

My flight was delayed twice. The first time because of “plane maintenance” and the second because the previous flight who supposedly “arrived early” took an obnoxiously long time to get off the plane. Total delay was over an hour for no reason. Not to mention your airline repeatedly changed our gate from one end of the terminal to the other. Not very happy about this experience. My previous flights with American haven’t had this many issues.

Very turbulent flight, no drinks, very little service, unorganized boarding, gate changed multiple times

We’ve had a year of delays with American, and this one was another flight to add to that list. It just reduced our vacation by a day! So frustrating. In-flight entertainment (TVs) weren’t working, There was no drinks service due to delivery issues.

The flight was delayed significantly. Communication during the flight was abrupt and caused some panic as we were navigating turbulence. It was also too loud and every announcement felt startling. The flight attendants did not offer any assurances and I felt unsettled most of the flight. The seats, floor and tray table was very dirty. The seat next to me was broken and the passenger sitting there was very uncomfortable. He had a spring in his back and his seat made terrible squeaking noises through the flight.

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.

When I agreed to give up my two seats because of overbooking by the airline, I should have been offered some sort of reward or credit towards a future flight. I was not. It was not until the next day when I mentioned it to a Jet Blue employee that I was advised to call 1-800-JetBlue. So here I am, having done Jet Blue a favor and I had to do the work to find out if I was going to get a credit. Such service

A nightmare. Scheduled flight delayed 2 hours then cancelled because pilot timed out . Unable to find another pilot. Really?! Weather certainly a factor, but JetBlue seemed totally unprepared for the chaos that ensued when flight routes were cancelled. More cancelled flights, finally many of us who had been bumped from other flights were allowed to board a Boston bound plane around 3:00am, delay after delay, sat on tarmac for another half hour while pilot dealt with weight distribution issues (?), arrived in Boston 4:30. Crew were wonderful- same attendants all day and night and they were exhausted. Fortunately for me and my son that Boston was our final destination, not so lucky for many who missed connecting flights.

Complete and total debacle from start to finish. HUGE mistake picking this airline. NEVER again! Rudest staff in the business.

The food took two hours to be delivered to my seat, when I'm on an overnight flight I want to sleep asap after take off

It's not JetBlues fault but there was a smell on the plane (possibly other travelers) and 3 children behind me that never quit whining. Soccor fans that were very loud. Pilot brought the plane down from high altitude quickly, dropping us hu dress of feet at a time. I've never felt that intense of dropping on other airlines (usually fly Southwest Airlines). But I arrived safely and I'm thankful for that.

Seats were great, the staff was great, and the food was about the best I've had on a plane, and is especially the best of any US-based carrier I've flown. Free Wi-Fi was also great.

The flight was delayed 14 hours and communication was very poor. No one seemed to know what was happening and the gate agent was trying to help people for several flights. She was by herself trying to help 100s of people.

Domestic flights are good. Just stay away from international travel

Flight left 2 hours late with no explanation as to the delay

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