$34 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 3/4. 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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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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Best Caribbean Islands Flight Deals from Hartford

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours

Punta Cana
Punta Cana1 stop$210
Santo Domingo
Santo Domingo1 stop$235
Montego Bay
Montego Bay1 stop$292
Oranjestad
Oranjestad1 stop$346
Nassau
Nassau1 stop$357
Kingston
Kingston1 stop$311
Simpson Bay
Simpson Bay1 stop$287
Providenciales
Providenciales1 stop$484
Bridgetown
Bridgetown1 stop$611
Port of Spain
Port of Spain2 stops$623
George Town
George Town1 stop$542
Willemstad
Willemstad1 stop$520
St. John's
St. John's1 stop$651
Puerto Plata
Puerto Plata1 stop$475
Aguadilla
Aguadilla1 stop$251

Good to know

Low season

September

High season

April

Cheapest flight

$34
Best time to beat the crowds with an average 22% drop in price.
Most popular time to fly and prices are also 0% lower on average.
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.

See more FAQs

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 $100 one-way - $186 round-trip
  • Book at least 1 week before departure in order to get a below-average price.
  • High season is considered to be June and July. The cheapest month to fly from Hartford is September.

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
DeltaOverall score based on 8219 reviews
8.0Comfort
7.9Entertainment
7.3Food
8.5Crew
8.2Boarding
Airline reviews

Boarding is, as it always is… horrible. Gate lice. Slow moving zones. Too many people with carry ons

10.0 ExcellentStephen, Feb 2025SFO - JFK
Read more Delta reviews

Boarding is, as it always is… horrible. Gate lice. Slow moving zones. Too many people with carry ons

I loved having a most black flight crew during Black History Month; rather by design or accident I appreciated the representation. ❤️

This was the second flight this week with flight attendant Marcus I’m not sure if his last name is Lane or Lang but this guy is awesome. He funny, attentive and his service is 5 stars. Marcus makes business travel more enjoyable !

Although the flight left late, we arrived early. It was one of the quickest boarding and off boarding experiences I’ve had. It was kind of annoying the only drinks they had were water, coffee, and tea. The flight was very smooth, temperature was just right, and flight attendants were friendly.

Rode in a smaller plane and short trip meant no snacks, no free wifi or tv. It was only 30min flight so honestly wasn’t a big deal to lack these items.

Lower number on this flight so spaced out passengers. Able to enjoy more room to relax during flight. It was lovely.

Kind staff. Snacks are small but that’s the new normal.

Overall, terrible. Flight from SFO was delayed due to “air traffic control issues”, and we were all mislead about connecting flights. Told “you have 20 minutes to catch your connection”. Reality was 5. We got to watch the plane sit at the bridge. Won’t fly Delta with a connection again.

The young man who was our flight attendant in first class was lazy and did not do his job well at all. Never offered drinks upon boarding - actually I take that back... said "are you okay with water" as if I do not want to get you anything else, only passed the snacks around once, got my drink order wrong and then never offered a second round of drinks. He was the worst I have ever seen on Delta and we fly a lot.

Great service. Great staff. Boarding was a little slow, but I think there was a service dog slowing things down.

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.

No food or entertainment, but flight very comfortable and on time.

Baggage claim was barbaric at Wilmington. I realize that this is a startup airline but if they hope to grow or even survive they need to upgrade this airport. There is no automated luggage carousel and at times you are not only fighting your fellow passengers to get to your bags but also passengers coming in from other flights who cross right in front of you

No frills, i.e., no drinks or snacks. One is charged for everything. The cost really adds up. The crew and flight attendants were excellent and very pleasant.

I always walk by a pallet of Avelo branded mini bottles of water on the tarmac, but I’ve never seen them in flight. Yup, not even water offered on a 3 hour flight. No wi-fi onboard. We just watch the flight crew on their phone for 3 hours every flight. At least a mid-flight trash pickup would be great. Better than my last flight, but they only could have gone up from there. Don’t use for business or ticketed vacation like Disney… too unreliable.

You get what you pay for. The plane was dirty and the seats were awful.

Nightmare airline. Avoid Avelo. Understaffed at check-in with long, slow lines. Inexplicably had two flights and only one plane. Not weather or maintenance related apparently. One was supposed to go to Myrtle Beach and one to Orlando. I imagine someone thought it would be better to fly the available plane to Myrtle Beach and back and then go to Orlando since that round-trip was shorter. This didn’t account for the human factor of an end-of-week Orlando flight being 85% Disney passengers and putting the flight on a six-hour delay in New Haven airport… which, if you’ve been there, is tiny and has nothing to do for 50 kids excited to get to Disney. This delay was announced at the time of departure. No one realized before the time of departure there was no plane on the ground? And no one thought… hey I think the Myrtle Beach crowd might be a better one to have wait if we’re going to make a choice here (mind you the initial inbound plane was coming from Orlando and supposed to be out aircraft… they literally said let just grab this plane because it’s here to get this other group out at the last second). There is/was zero customer service desk for Avelo in HVN and there were no updates/announcements throughout the day. Plane still gets back late and we finally leave. No wi-fi on these planes, no snack or even water. I know this is budget airline, but expected at least a water after 8 hours of travel day. This should have been offered in terminal too. We land… hooray. Would you believe there is no ground crew to get the plane in to the gate… for 27 minutes. 27 minutes!!! At this point the rental car center is closing in 10 minutes, kids on the plane are crying again, and everyone is talking about how they’re never flying Avelo again. Finally get off. Bags are out at baggage claim right away (finally something right?), but they’ve stopped the carousel immediately and there is no baggage service rep. People are climbing over the carousel to get to the far side (if you’ve ever been to MCO you’ve seen it) because obviously they just stopped it immediately once all the bags were out. This airline is a dumpster fire. Icing on the cake was that while everyone was stuck in HVN, they were setting up for a celebration of their millionth passenger tomorrow. I bet 995,000 of those will never fly the airline again. Don’t fly Avelo. You’ve been warned.

Airline was the only available airline during the Southwest cancellation. It was easy to book. Lowest available fair. Convenient airports. Everything was great. Problem was, they didn’t release what gate flight was departing. The woman at the ticket booth didn’t know which terminal they were boarding and wanted me to wait in 30+ minute line versus telling me to look for flight kiosk. Burbank gate was packed. Otherwise the flight was perfect!!

Except for the 28 minute delay leaving and the earlier reschedule to a later takeoff time the flight was good.

Loved the leg room and tvs screens on the seats and free WiFi. Wish the price was lower and could save by rebooking

No music app working: no economy meal on five hour flight; hour on tarmac at the end waiting for a gate. Flight itself was smooth and easy.

It took 1-1/2 hours to get our luggage after we landed. That to me is unacceptable

The flight was delayed for 4 hours. Once onboard the crew was wonderful.

Overall was excellent. Will definitely us JetBlue in the future.

Very well organized both boarding and deplaning. Very satisfied with the service I received.

I rate it is good we had a 4-hour travel delay at one point but JetBlue gave out food vouchers and travel points credits for another flight so they try to make up for it

Smooth boarding and friendly crew. Unfortunately as soon as we boarded the unit that provides air circulation failed. The pilot informed us and requested maintenance technicians to check it out. The plane became uncomfortably warm without any fresh air coming in. Plus the repair delayed our departure. I am glad the maintenance crew were able to fix the problem. I also was without use of my tv monitor for the first 1/3rd of the trip.

Flight was on time arrived at the destination 10min early they kept in touch via email

I don’t understand the purpose of the orange “priority” tag on my bag. This tagged, my bag is last or near to the last bag to come down the carousel at IAH.

The tv monitor in front of my seat was not responding. The flight crew reset it and it still didn’t work.

The agents was very rude and they charged me $50 for a carry-on bag saying that it was too big and then I saw someone going on a plane with the same size bag as me

Liked nothing. As per previous segment it was delay delay delay.

Terrible. First of all we were delayed 4 3/4 hours departing Honolulu. As we had to leave our condo and the rental car had to be returned we had to go to the airport. Even though we had a business class boarding pass to Washington, since we did not have business class to Montreal we could not access the lounge without paying a $59 fee each. This does not make sense to us. Since we could not meet our original connection United booked us to Montreal via New York LaGuardia on Air Canada. In Washington a further delay got us into LaGuardia too late to make our connection to Montreal so we were booked on another Air Canada flight 3 hours later. We were originally scheduled to arrive in Montreal at 10:40 and arrived at 19:55. A totally exhausting day, United did not offer a meal voucher or any type of compensation. Air Canada did give us a digital meal voucher. The food in United business class is poor among all meals offered. The pods look nice but are not that confortable. Overall would not fly on United again.

Plenty of room for me and the cat in Premium Economy. Seat was comfortable. Boarding was a breeze. The lady at the special check-in desk was great, super helpful and professional.

For the most part united was a good experience, how ever when they came by with the snacks and water, they completely passed by my wife and I. As we were in separate rows. On a 5 hr flight we were not offered water

Fantastic crew. Flight was delayed at last minute but we were given updates every 20 minutes and the crew was so friendly and considerate. I miss the touch screens on the back of the seats, wish they would bring that back though.

Our seats were all the way in back of the plane,

Food choices were very limited. Taste of the dishes was average.

Delays on all NY flights. There was no communication on why but they didn’t say it was weather. Other carriers were not delayed.

The flights were terribly delayed and then cancelled which forced us booking another night at the hotel. Very poor management from American Airlines

Extraordinary service in business class, and very good breakfast and snacks. A really lovely flight.

Same as before being upgraded to business class made it perfect

I flew out of Reagan National. My flight was delayed, delayed, delayed, and then canceled ...THREE TIMES over TWO DAYS. Staff were seemingly not empowered to provide information on why the flights were screwed up. A real nightmare.

They cancelled our flight without warning OR a refund. Never doing business with American Airlines again! This is the second AA booked trip in a row that we've had challenges with.

Crew was late. Baggage was late. 2hs inside the plane waiting fro de-icing and traffic. A 3:30hs flight ended up being almost 6hs inside the airplane.

Flight delayed on both ends - have a gate ready at DCA, don't make us sit for 30min after being late to take off as well.

The seats were crammed and the guy in front of me wouldn't stop reclining. If AA is cramming extra rows in, they need to take away the reclining in coach. My knees were smashed for 4 1/2 hours and I was very close to confronting the passenger in front of me.

This flight didn’t happen because AA agents didn’t let us board the flight

Book cheap flights from Hartford to Caribbean Islands

Recent round-trip flight deals

 
These are the cheapest round-trip flights from Hartford to Caribbean Islands found on KAYAK in the last 72 hours.
3/25Tue
nonstopFrontier
3h 50mBDL-SJU
4/8Tue
nonstopFrontier
4h 06mSJU-BDL
$88
3/4Tue
nonstopFrontier
3h 50mBDL-SJU
3/6Thu
nonstopFrontier
4h 19mSJU-BDL
$89
3/24Mon
nonstopJetBlue
3h 48mBDL-SJU
3/27Thu
nonstopJetBlue
4h 10mSJU-BDL
$218
3/24Mon
1 stopDelta
8h 43mBDL-SJU
4/8Tue
1 stopDelta
7h 02mSJU-BDL
$227
3/22Sat
nonstopJetBlue
3h 48mBDL-SJU
4/1Tue
nonstopJetBlue
4h 01mSJU-BDL
$228
3/28Fri
1 stopDelta
8h 43mBDL-SJU
4/3Thu
1 stopDelta
7h 02mSJU-BDL
$237
3/18Tue
2 stopsAmerican Airlines
8h 30mBDL-NAS
3/27Thu
2 stopsAmerican Airlines
8h 55mNAS-BDL
$361
3/6Thu
1 stopAmerican Airlines
9h 33mBDL-STT
3/12Wed
2 stopsAmerican Airlines
16h 22mSTT-BDL
$373
3/24Mon
1 stopUnited Airlines
5h 45mBDL-NAS
3/26Wed
2 stopsUnited Airlines
19h 08mNAS-BDL
$451
3/12Wed
2 stopsUnited Airlines
10h 30mBDL-STT
3/17Mon
1 stopUnited Airlines
6h 39mSTT-BDL
$463

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Recent one-way flight deals

 
Only flying one-way? Below are some of the best one-way flight deals from Hartford to Caribbean Islands found on KAYAK in the last 72 hours.
3/4Tue
nonstopFrontier
3h 50mBDL-SJU
$34
3/3Mon
nonstopFrontier
3h 50mBDL-SJU
$38
3/17Mon
nonstopJetBlue
3h 48mBDL-SJU
$109
3/1Sat
1 stopAmerican Airlines
7h 00mBDL-SJU
$114
3/1Sat
1 stopAmerican Airlines
9h 33mBDL-SJU
$116
4/21Mon
1 stopDelta
7h 30mBDL-SJU
$135
3/1Sat
2 stopsUnited Airlines
14h 41mBDL-SJU
$141
4/15Tue
1 stopDelta
10h 00mBDL-NAS
$152
5/31Sat
nonstopJetBlue
3h 44mBDL-SJU
$165
4/26Sat
2 stopsUnited Airlines
10h 59mBDL-SJU
$180

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Last minute flights from Hartford to Caribbean Islands

Last minute flight, train and bus deals

 
These last-minute flight deals are the cheapest flights found on KAYAK in the last 72 hours for flights from Hartford to Caribbean Islands that are departing in the next 10 days.
2/25Tue
nonstopFrontier
3h 50mBDL-SJU
3/6Thu
nonstopFrontier
4h 19mSJU-BDL
$96
2/25Tue
nonstopFrontier
3h 50mBDL-SJU
3/5Wed
nonstopFrontier
4h 19mSJU-BDL
$99
2/24Mon
nonstopJetBlue
3h 49mBDL-SJU
2/27Thu
nonstopJetBlue
4h 10mSJU-BDL
$259
2/22Sat
multi-stopDelta
8h 48mBDL-SJU
2/26Wed
multi-stopDelta
11h 09mSJU-BDL
$268
2/22Sat
multi-stopAmerican Airlines
9h 16mBDL-SJU
3/1Sat
multi-stopAmerican Airlines
9h 35mSJU-BDL
$274
2/21Fri
nonstopJetBlue
3h 47mBDL-SJU
3/3Mon
nonstopJetBlue
4h 10mSJU-BDL
$279
2/23Sun
multi-stopDelta
8h 47mBDL-SJU
3/2Sun
multi-stopDelta
8h 03mSJU-BDL
$288
2/22Sat
multi-stopAmerican Airlines
9h 35mBDL-SJU
2/26Wed
multi-stopAmerican Airlines
10h 51mSJU-BDL
$289
2/22Sat
multi-stopUnited Airlines
6h 30mBDL-SJU
2/27Thu
multi-stopUnited Airlines
13h 00mSJU-BDL
$358
2/25Tue
multi-stopUnited Airlines
14h 41mBDL-SJU
2/26Wed
multi-stopUnited Airlines
13h 00mSJU-BDL
$359

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Everything you need to know for your flight to Caribbean Islands

Information on your arrival and departure airports

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