$110 Find Cheap Flights from Hartford to Caribbean Islands - Compare and Save

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Cheap Flights from Hartford to Caribbean Islands

Cheapest round-trip prices found by our users on KAYAK in the last 5 days
Punta Cana
Punta Cana1 stop$302
Santo Domingo
Santo Domingo2 stops$365
Montego Bay
Montego Bay1 stop$332
Oranjestad
Oranjestad1 stop$407
Nassau
Nassau1 stop$312
Kingston
Kingston2 stops$461
Simpson Bay
Simpson Bay2 stops$332
Providenciales
Providenciales1 stop$518
Port of Spain
Port of Spain1 stop$359
Bridgetown
Bridgetown1 stop$424
George Town
George Town1 stop$357
Willemstad
Willemstad1 stop$371
Aguadilla
Aguadilla1 stop$312
St. John's
St. John's1 stop$684
Puerto Plata
Puerto Plata1 stop$576
Punta Cana
Punta Cana1 stop$302
Santo Domingo
Santo Domingo2 stops$365
Montego Bay
Montego Bay1 stop$332
Oranjestad
Oranjestad1 stop$407
Nassau
Nassau1 stop$312
Kingston
Kingston2 stops$461
Simpson Bay
Simpson Bay2 stops$332
Providenciales
Providenciales1 stop$518
Port of Spain
Port of Spain1 stop$359
Bridgetown
Bridgetown1 stop$424
George Town
George Town1 stop$357
Willemstad
Willemstad1 stop$371
Aguadilla
Aguadilla1 stop$312
St. John's
St. John's1 stop$684
Puerto Plata
Puerto Plata1 stop$576
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?

The cheapest ticket to Caribbean Islands from Hartford found in the last 5 days was to San Juan, at $164 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 $164.

What is the cheapest time of day to fly to Caribbean Islands?

The cheapest time of day to fly to Caribbean Islands is generally in the afternoon, when round-trip flights cost $336 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?

No, with an average price for the route of $380, prices are generally cheapest when you fly direct.

What is the cheapest month to fly from Hartford to Caribbean Islands?

The cheapest month for flights from Hartford to Caribbean Islands is January, when tickets cost $479 (return) on average. On the other hand, the most expensive months are July and June, when the average cost of round-trip tickets is $626 and $614 respectively.

What’s the cheapest day of the week to fly from Hartford to Caribbean Islands?

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 Sundays for better deals.

How far in advance should I book a flight from Hartford to Caribbean Islands?

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

$110
Best time to beat the crowds with an average 11% drop in price.
Most popular time to fly with an average 22% increase in price.
Flight from Hartford to San Juan

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 $150 one-way - $279 round-trip

Reviews of the top 5 airlines serving from Hartford to Caribbean Islands

 
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 4215 reviews
7.5Entertainment
7.0Food
8.1Boarding
8.6Crew
8.0Comfort
Airline reviews

Seated at front bulkhead for a smidge extra leg room away from home and on flight back home. Away crew was very proactive about assuring our carryons had space close behind us (because no seat in front of us our personal items had to be in a small bin overhead). They actively required passengers place overhead luggage on its side so more items could fit in bins. Home crew made no such efforts. I had to struggle back rows to get overhead bags upon landing, no crew help then either, and some disgruntled passengers as I and others retrieved our bags. There was a system that worked pretty well. The home bound crew just didn't feel like working.

4.0 OkayMather, Aug 2026
Read more Southwest reviews

Seated at front bulkhead for a smidge extra leg room away from home and on flight back home. Away crew was very proactive about assuring our carryons had space close behind us (because no seat in front of us our personal items had to be in a small bin overhead). They actively required passengers place overhead luggage on its side so more items could fit in bins. Home crew made no such efforts. I had to struggle back rows to get overhead bags upon landing, no crew help then either, and some disgruntled passengers as I and others retrieved our bags. There was a system that worked pretty well. The home bound crew just didn't feel like working.

Southwest has inacted unfriendly customer policies like other airlines. Watch the fine print very carefully if you are having to alter flight arrangements. Rules are now complicated and very stilted to travelers sacrificing travel funds (unlike before where the simple, straight forward flight change policy was worth the extra premium for ticket price.) On the positive side, SW Flight crews are still wonderfully helpful.

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 plane was a rather tired 737-800, with old style small luggage bins. Poor air flow. USB charger in the infotainment system was not functioning. The flight was 2 hours late due to crew rest requirements (not their fault). On arrival in Seattle, waited on the tarmac for 30 minutes with very few updates from the crew.

Flight was delayed and we were on the runway after landing for 30 mins

The plane is old. There was water dripping fown from the air cooling system. The toilets were mot that clean

We were delayed so pilots can rest and had no WiFi the whole trip. First class seats are small compared to other planes

The experience was bad. Flight was delayed to handle maintenance (understandable) but still there was some dew forming and dropping as droplets on few seats. Internet at best was allowing some browsing but at a snail pace.

We were delayed 2 hours because of a broken seat. Other than that it was a very nice flight.

There needs to be better accommodations for waiting passengers. A a designated standing space that is separated and away from concourse traffic.

My seats are comfortable because I choose to fly in the exit rows and this time upgraded to first class with minimum sky miles. Otherwise, I would not be happy in regular seats or even middle comfort seats. Onboarding on the return flight from Nashville to Atlanta was hot and very uncomfortable for over 30 minutes due to extreme hot weather. However, Delta should provide some other air flow option as it was almost unbearable until 10 minutes after take-off. First class seats should be equipped with cup holders. Currently, the middle console is used and is flat and prone to spilling drinks.

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.

Flight did not have wifi service. It was experiencing technical difficulties. Definitely and old plane that needs updating.

Very Poor. Significant delays getting to Chicago and then very poor communication on delays in Chicago to Cleveland. We could have rented a car and driven there faster than the delays ended up being.

A little more friendliness from that crew of the day.

The app logs you out right when you are boarding requiring all passwords and reservation number for the flight. Super annoying

The pre-order only approach for fresh food is really challenging

This flight has a history of leaving late, however, I was pleasantly surprised that it was not delayed this day. The flight went smooth, except I was in a window seat and the wall and my feet were freezing. I found it difficult to sleep due to being so cold, I also was using 2 provided UAL blankets and could not get my feet warm. This was annoying, but I still made it there on time and safe.

Staff didn't seem confident about the ingredients in my lactose intolerance meal

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

Luggage handling and communication is extremely poor. I landed in india 15th and recived luggage today. Based on my itag the luggage was in Germany. They kept me in dark. Etihad num er in india was non operatuonal. Had to call USA etihad. It should not be so difficullt. I came for 1 week business trip everything was screwed . This is the first and also will be last for me

There was no service on the flight even though there was no turbulence or any other issues on the flight. Nobody greeted at the entry or leaving the airplane, staff crew looked annoyed and not helpful at all.

mechanical problem delayed more than 2 hours on the run way.

I paid extra for a seat up front and at last minute was moved to the 2nd to last row - which I could have had for free. No reason and no refund. Really great customer service American

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.

My screen didn’t work, my seat didn’t recline, the flight attendant was rude and completely dismissive, the airplane was freezing, the seats are way old, slanted and uncomfortable. I payed for a full ticket and got a horrific experience, with a flight attendant who dismissed me even though I was calm respectful and polite.

Very poor help no one answering a question regarding seating. Very rude staff. They don’t care, as if it’s not part of their job. Flight was delayed for no good reason and no apologies given.

It was my worse flying experience. It was my first time and last time flying with Jet Blue.

The wifi didn't work and I needed to do some work. This was a business trip.

It was my first time in Jetblue flight in 10+ years(?) and the experience was horrible. You were better before. There were ATC delays sitting/waiting in the tarmac for 2 hours, I understand that this isn't Jetblue's problem but how the matter was handled poorly is. Cabin was so warm and hot couldn't get it to cool down for the entire waiting period worse, even during cruise flight. Start, the passengers were spoken to and treated like a little children with no respect. Constant/multiple annoying tone/voice PA announcements of mentioning "... only big/large suitcases are for the bin and small ones need to be placed under the seat, etc,..." I see that flight was delayed and crew were trying to get the plane ready to board as soon as they can but the way they presented was lack of better word, condesending and scolding tone to cattle. It was definite unpleasant, unwelcoming flight experience I have ever had with Jetblue. Whatever happen to smiles and fun employees , pleasant/helpful gate agents, flight attendants, crews, where have they gone? It was dissapointing flight experience overall from everyone. Sorry for the direct transparency.

Flight was cancelled as JetBlue could not find a pilot. Communication was poor and they did nothing for stranded passengers. Flight they rebooked us on was 4 days out.

JetBlue cancelled the flight. We had to rebook on another airline.

JetBlue cancelled the flight along with hundreds of others, for no apparent reason. no recourse, no rebooking options. never booking with them again

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