$51 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 1/13. 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
0 bags

Search 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.

Best Caribbean Islands Flight Deals

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

Punta Cana
Punta Cana1 stop$244
Montego Bay
Montego Baynonstop$267
Santo Domingo
Santo Domingo1 stop$307
Oranjestad
Oranjestad1 stop$274
Nassau
Nassau1 stop$369
Simpson Bay
Simpson Bay1 stop$244
Kingston
Kingston1 stop$316
Providenciales
Providenciales1 stop$445
Bridgetown
Bridgetown1 stop$563
Port of Spain
Port of Spain1 stop$557
George Town
George Town1 stop$440
Willemstad
Willemstad2 stops$533
St. John's
St. John's1 stop$626
Puerto Plata
Puerto Plata1 stop$443
Aguadilla
Aguadilla1 stop$178

Good to know

Low season

September

High season

February

Cheapest flight

$51
Best time to beat the crowds with an average 22% drop in price.
Most popular time to fly and prices are also 5% 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 to Caribbean Islands from Hartford 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 to Caribbean Islands with an airline and back to Hartford 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 to Caribbean Islands from Hartford 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 $118 one-way - $193 round-trip

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 8755 reviews
7.9Comfort
7.9Entertainment
8.2Boarding
8.5Crew
7.3Food
Airline reviews

I sat in comfort plus. It was fine. Seats were comfortable. I got drinks and snacks.

8.0 ExcellentAndrew, Nov 2024MCO - LGA
Read more Delta reviews

I sat in comfort plus. It was fine. Seats were comfortable. I got drinks and snacks.

Crew was nice. Flight was timely. Seats could be better as well as the food considering it’s first class.

Left on time and arrived early this extending our 31 minute transfer. Bags made it also!

Good and consistent Printer in lounge did not work for me :(

Most of my discomfort was going through TSA. However, the Delta seats had inadequate leg room and I tried my very best to connect to the wi-fi and it was a cumbersome process that finally gave me the info that I needed to sign in AFTER I had completed the flight...Why make it so difficult to use? That said I really really appreciate the pilot taking a little extra time to avoid a bad storm area and both landings in Atlanta and Orlando were flawless to my delight!!!

Delayed in taking off because no flight crew. The in seat entertainment was working properly.

All fine save for the abominable catering. Really gone downhill. We found it all inedible.

I upgraded to first class only to find out that I still had no access to the sky lounge without a sky miles card or AmEx (something that should be emphasized outside of the fine print!) Also, no food or drink service provided during the flight, so I basically paid 4x more just for “free” checked baggage and a bigger seat. Not worth it.

I appreciated friendly service from check-in, to boarding, to in-flight amenities! Attendants were accommodating and helpful. Thank you! Elaine

Delta was really good about being transparent with why we were delayed it’s just that’s the plane was really old and outdated and a lot of the comfort and amenities we know Delta to have did not shine through

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

Communication with the customer and stay is important. Staff off with a minor inconvenience but it worked out of course. Also this was a very old Mint Class plane. They snuck this one in on us. The updated aircraft are much better.

The flight itself was fine, but the boarding process was extremely frustrating. There is no one scanning boarding passes - passengers just scan themselves and enter the jetway. By the time my husband and I got on the plane and were halfway to our seats they determined there were too many bags on the plane and everything at that point needed to be checked. This created a lot of unnecessary chaos. They should have alerted people before getting on the plane that they would need to start checking bags instead of waiting until people were already on the plane.

The best flight I’ve had in a while. The plane was like 25% capacity, if that. Smoothest boarding and deplaning process I’ve ever experienced. Wish all flights were this smooth.

Did not enjoy this flight at all. All of my coworkers flew delta and I chose JetBlue because I really value how simple the WiFi and entertainment is and this flight I didn’t get either. Crew staff was unsympathetic to my system not working, everyone I asked for help with was extremely bothered by my request for help.

In flight on demand didn't work at our seats. Only a single beverage/snack run.

Little snafu at boarding. Staff communicated with gate poorly. Flight attendant was rude making disembark early. This was an older mint class. Needs an overhaul for sure. Food was good. The male flight attendant was really nice.

My encounter with the entertainment services provided on board was moderate; the functionality of the Wi-Fi connection was either sluggish or nonoperational, while the display screens were antiquated and suffered from poor visibility. On the positive side, the cabin exuded a sense of expansiveness, and the crew exhibited amiable and accommodating behavior throughout the journey.

Everything was great except for some reason crew and ground crew could not figure out how to deal with an electric wheelchair and it delayed us 20-30mins. Was pretty frustrating for passengers and the captain.

There was no USB plug in my section of the plane. So I could not charge my phone. Also, there was no screen to watch movie or anything like that. Wish I had known that in advance, I would’ve brought my iPad.

Had a crying baby and a toddler behind me so it was difficult to get comfortable. Searing was tight even for a relatively small person like myself (5’8” 155). Fast flight but arrived so early the gate assigned was still occupied by another plane so we had to wait for about 20-25 minutes to get reassigned to a new gate and get over there.

Best part: It’s operated by All Nippon Airways. It’s quite literally comfortable, reliable and respected from boarding to landing each and every time. It’s perfection without extremity in lavishness — it’s how flying should always be!

The flight attendants were unhelpful. It was a packed flight, and usually a flight attendant would help find a spot in the bin for your carry on or shift things around. Neither made any effort to do so. Also, I had to then check my bag. I was told it would be on the carousel in YYZ, but it came up on the jetway. So lucky I saw others standing around for their bags. I would have walked straight past this and on to the carousel. They could have at least told me that they had given me wrong information. Very unsatisfactory.

Made all groups except 2 check despite ample bin space. Inflight WiFi and entertainment didn’t work most of the time.

The check-in process is not the best They should have agents in site to help with any problem especially a rebook. Why does one have to get on the phone when there were at least 8 agents around that could have help?! Flying is stressful as it is and having someone willing to do their customer service will ease some of the stress.

It was a good flight. Nothing comes to mind about how it could have been better. It was a newer plane, seemed like a great upgrade from your older ones. Staff was very good as well.

Seats are smaller and harder than other airlines we have travels with. Food was edible but no good. The sandwich was the only thing I would eat again. They did have a lot of movies to watch.

boarding was uneventful. Snack was pathetic. A tiny fruit bar. Entertainment was limited to just select movies on your own tablet or phone. No live TV. I recently flew Jetblue and they had unlimited snacks and live satellite TV the entire flight. My seat was an exit seat, 20A. It was super uncomfortable. It felt cramped and the middle seat was taken up by a large woman who pushed into my shoulder and arm. Horrible flight.

I liked that the flight to Kosice was on time, the service was excellent and we arrived to Vienna early. The only thing I did not like, is that I had to pay for my suitcase $75. Bummer

My flight attendant was attentive! The elderly person next to me was flatulent and the flight attendant could see that I was in distress and brought me some face masks

It was as expected for such a short flight. No complaints

The departing flight from Newark to Charlotte was fine. It was the returning flight from Charlotte to Newark that was awful. We had scheduled an 8:35pm return flight time. We got delayed TEN times all the way to 5am in the morning! We were told over 4 different excuses as to why the flight kept getting delayed. First it was the flight crew needed to rest, then it was something technical with the plane, then it was something with air traffic control, and finally it was because they couldn’t find a captain and had to wait until the morning so the captain could get some rest. It was terrible sleeping overnight in the airport. They offered a $12 meal voucher. That was it! And the only place open in the middle of the night was Dunkin’ Donuts who didn’t even accept the voucher. They should have cancelled the flight much earlier on in the evening instead of just stringing us along hour by hour with more delays. Not professional and unacceptable. There was no refund for inconvenience. I probably will not be flying American Airlines again.

This leg they tried and did well with what they had to work from.

It was nice being on a flight that had working wifi. The boarding was quick - why don’t all airlines have small boarding groups window to aisle? Makes so much sense!!! I was disappointed to be the first person stopped to have to gate check my carryon. Especially when there was plenty of overhead space at the back! But I get it…keeps it moving. Crew was nice.

The flight was as good as it gets when flying. On time departure and arrival plus no lost luggage.

My boarding pass wouldn't pull up in the app very easily and had to really dig through my email. That caused a delay in TSA..

Packed commercial flight was as comfortable as can be expected

My seat was very worn. Otherwise I had an excellent flight

I'm not a valued flyer so I'm always in the last group to board...that sucks, always

Boarding was slow the scanner broke mid through boarding and they had to manually do it

Average, boarding was ok, the eye scanner broken mid way through boarding they ahd to do it manually. Did not eat any food, Not even water was offered for free.

Boarding attendant was rude. Crew on the plan were more interested in talking amongst themselves and did not ask parentage if they needed anything or even walk down the isles.

Flight was ok with exception of the multiple delays. As with all Spirit flights, the sights are extremely uncomfortable and lack leg space. However, the price savings is the plus.

WiFi didn’t work despite paying for it. Crew was nice.

I upgraded my ticket at the ticket counter and was not informed of the huge bottleneck at TSA pre check. It took me over an hour to get through the line at this small airport and although I ran to the gate and reached it prior to scheduled departure, it had already pushed pack. I missed the flight. Spirit rebooked me on a flight to Orlando that evening, which would require me to then rent a car and drive to FLL. For scheduling reasons, I determined it be would better to rent a car in Pensacola and drive it to my destination in FLL. Spirit called me that evening and asked me if I was going to board the plane. I explained no, for scheduling reasons. The person apologized and said I would receive a refund, but I have not heard back. Certainly, I ought to be refunded the upgrade I paid for at the counter.

The staff from LAX to New Orleans were rude but the staff from New Orleans to LAX were nice!

Did what they needed to do. Brought us from point A to point B timely and without issue. Boarding through deplaning smooth.

Direct 2.5 hour flight good. Free snacks and coffee, water, or soft drinks not available...bad.

Atlanta airport gate area floor and nearly all seats disgusting. Spirit airlines crew fantastic!!

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.
12/4Wed
nonstopFrontier
3h 58mBDL-SJU
12/7Sat
1 stopFrontier
13h 03mSJU-BDL
$126
12/11Wed
nonstopFrontier
3h 58mBDL-SJU
12/18Wed
1 stopFrontier
12h 49mSJU-BDL
$127
1/24Fri
nonstopJetBlue
3h 46mBDL-SJU
2/3Mon
nonstopJetBlue
4h 04mSJU-BDL
$240
1/14Tue
1 stopAmerican Airlines
10h 50mBDL-SJU
1/17Fri
1 stopAmerican Airlines
13h 13mSJU-BDL
$248
1/22Wed
1 stopUnited Airlines
6h 17mBDL-SJU
1/24Fri
2 stopsUnited Airlines
13h 02mSJU-BDL
$258
1/23Thu
nonstopJetBlue
3h 46mBDL-SJU
1/26Sun
nonstopJetBlue
4h 04mSJU-BDL
$259
1/25Sat
2 stopsUnited Airlines
14h 23mBDL-SJU
2/1Sat
2 stopsUnited Airlines
14h 58mSJU-BDL
$278
1/19Sun
2 stopsAmerican Airlines
19h 27mBDL-STT
1/27Mon
2 stopsAmerican Airlines
16h 56mSTT-BDL
$288
1/28Tue
1 stopDelta
7h 17mBDL-PUJ
2/4Tue
1 stopDelta
8h 06mPUJ-BDL
$410
1/11Sat
1 stopDelta
7h 22mBDL-MBJ
1/23Thu
1 stopDelta
7h 07mMBJ-BDL
$425

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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.
1/13Mon
1 stopFrontier
13h 54mBDL-SJU
$51
12/31Tue
nonstopFrontier
3h 58mBDL-SJU
$53
2/19Wed
1 stopAmerican Airlines
7h 02mBDL-SJU
$124
1/23Thu
nonstopJetBlue
3h 46mBDL-SJU
$130
12/23Mon
1 stopAmerican Airlines
16h 19mBDL-NAS
$131
1/20Mon
1 stopJetBlue
8h 02mBDL-BQN
$131
1/26Sun
2 stopsUnited Airlines
16h 52mBDL-BQN
$139
12/31Tue
1 stopDelta
7h 42mBDL-STT
$142
11/27Wed
1 stopDelta
7h 41mBDL-SJU
$162
1/20Mon
2 stopsUnited Airlines
16h 52mBDL-BQN
$167

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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.
11/25Mon
nonstopFrontier
3h 54mBDL-SJU
11/27Wed
nonstopFrontier
4h 08mSJU-BDL
$204
11/25Mon
nonstopFrontier
3h 54mBDL-SJU
11/27Wed
nonstopFrontier
4h 08mSJU-BDL
$205
11/23Sat
nonstop
3h 54mBDL-SJU
12/3Tue
multi-stop
26h 23mSJU-BDL
$267
11/24Sun
multi-stopAmerican Airlines
10h 50mBDL-SJU
12/7Sat
multi-stopAmerican Airlines
9h 18mSJU-BDL
$296
11/23Sat
nonstop
3h 54mBDL-SJU
12/3Tue
multi-stop
26h 23mSJU-BDL
$301
11/24Sun
multi-stopSpirit Airlines
10h 49mBDL-SJU
12/3Tue
multi-stopSpirit Airlines
26h 23mSJU-BDL
$327
11/26Tue
multi-stopSpirit Airlines
10h 49mBDL-SJU
12/3Tue
multi-stopSpirit Airlines
26h 23mSJU-BDL
$330
11/24Sun
multi-stopAmerican Airlines
10h 11mBDL-SJU
11/25Mon
multi-stopAmerican Airlines
10h 26mSJU-BDL
$338
11/22Fri
multi-stopUnited Airlines
6h 17mBDL-SJU
11/22Fri
multi-stopUnited Airlines
13h 09mSJU-BDL
$378
11/22Fri
multi-stopUnited Airlines
6h 17mBDL-SJU
11/23Sat
multi-stopUnited Airlines
10h 49mSJU-BDL
$414

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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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