$121 Find Cheap Flights from Caribbean to Hartford - Compare and Save

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Cheap Flights from Caribbean to Hartford

 
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Caribbean to Hartford

Wed, Oct 7 - Sat, Oct 10
American Airlines Logo
3:46 pm - 11:53 pmSTT  Saint Thomas Island Cyril E King-BDL Hartford Bradley Intl
8h 07m1 stop Miami
American Airlines Logo
7:15 pm - 2:55 pmBDL  Hartford Bradley Intl-STT Saint Thomas Island Cyril E King
19h 40m2 stops Philadelphia Miami
$218American Airlines
Wed, Sep 9 - Wed, Sep 23
Multiple Airlines Logo
2:57 am - 10:07 pmSJU  San Juan Luis Munoz Marin Intl-BDL Hartford Bradley Intl
19h 10m2 stops Orlando Raleigh-Durham
Multiple Airlines Logo
9:25 pm - 1:10 amBDL  Hartford Bradley Intl-SJU San Juan Luis Munoz Marin Intl
3h 45mnonstop
$226Multiple Airlines
Wed, Nov 4 - Sat, Nov 7
United Airlines Logo
5:50 pm - 11:59 pmSJU  San Juan Luis Munoz Marin Intl-BDL Hartford Bradley Intl
7h 09m1 stop Washington, D.C. Dulles Intl
United Airlines Logo
9:38 am - 9:00 pmBDL  Hartford Bradley Intl-SJU San Juan Luis Munoz Marin Intl
10h 22m1 stop Chicago O'Hare Intl
$228United Airlines
Wed, Nov 4 - Sat, Nov 7
United Airlines Logo
7:40 am - 9:47 pmSJU  San Juan Luis Munoz Marin Intl-BDL Hartford Bradley Intl
15h 07m2 stops Houston George Bush Intcntl Chicago O'Hare Intl
United Airlines Logo
9:38 am - 9:00 pmBDL  Hartford Bradley Intl-SJU San Juan Luis Munoz Marin Intl
10h 22m1 stop Chicago O'Hare Intl
$228United Airlines
Thu, Nov 12 - Tue, Nov 17
American Airlines Logo
8:25 am - 2:30 pmSJU  San Juan Luis Munoz Marin Intl-BDL Hartford Bradley Intl
7h 05m1 stop Miami
American Airlines Logo
5:30 am - 10:32 pmBDL  Hartford Bradley Intl-SJU San Juan Luis Munoz Marin Intl
16h 02m1 stop Miami
$228American Airlines
Tue, Sep 1 - Sat, Sep 5
Frontier Logo
8:45 am - 12:47 pmSJU  San Juan Luis Munoz Marin Intl-BDL Hartford Bradley Intl
4h 02mnonstop
Frontier Logo
1:42 pm - 5:46 pmBDL  Hartford Bradley Intl-SJU San Juan Luis Munoz Marin Intl
4h 04mnonstop
$232Frontier
Wed, Sep 2 - Mon, Sep 7
Frontier Logo
8:45 am - 12:47 pmSJU  San Juan Luis Munoz Marin Intl-BDL Hartford Bradley Intl
4h 02mnonstop
Frontier Logo
1:42 pm - 5:46 pmBDL  Hartford Bradley Intl-SJU San Juan Luis Munoz Marin Intl
4h 04mnonstop
$233Frontier
Thu, Sep 3 - Sun, Sep 6
JetBlue Logo
7:00 am - 10:54 amSJU  San Juan Luis Munoz Marin Intl-BDL Hartford Bradley Intl
3h 54mnonstop
JetBlue Logo
7:59 pm - 11:52 pmBDL  Hartford Bradley Intl-SJU San Juan Luis Munoz Marin Intl
3h 53mnonstop
$237JetBlue
Wed, Oct 7 - Sun, Oct 11
JetBlue Logo
8:30 am - 12:27 pmSJU  San Juan Luis Munoz Marin Intl-BDL Hartford Bradley Intl
3h 57mnonstop
JetBlue Logo
7:31 pm - 11:28 pmBDL  Hartford Bradley Intl-SJU San Juan Luis Munoz Marin Intl
3h 57mnonstop
$237JetBlue
Wed, Oct 14 - Wed, Oct 28
Multiple Airlines Logo
11:17 am - 2:21 pmBQN  Aguadilla Borinquen-BDL Hartford Bradley Intl
27h 04m1 stop Orlando
Multiple Airlines Logo
12:00 pm - 6:49 pmBDL  Hartford Bradley Intl-BQN Aguadilla Borinquen
6h 49m1 stop Orlando
$381Multiple Airlines
Useful Info

Good to know

Low season

September

Cheapest flight

$121
Best time to beat the crowds with an average 7% drop in price.
Most popular time to fly with an average 23% increase in price.
Flight from San Juan to Hartford

FAQs for booking flights from Caribbean to Hartford

  • How does KAYAK find such low prices on flights from Caribbean to Hartford?

    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 Caribbean to Hartford.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Caribbean to Hartford?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Hartford from Caribbean 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 Caribbean to Hartford?

    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 Hartford with an airline and back to Caribbean with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Caribbean to Hartford?

    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 Hartford from Caribbean up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Reviews of the top 5 airlines serving from Caribbean to Hartford

 
Need help choosing which airline to fly with from Caribbean to Hartford? 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.
7.8
DeltaOverall score based on 8505 reviews
8.1Boarding
7.8Comfort
7.2Food
8.5Crew
7.8Entertainment
Airline reviews

They announced a mechanical issue prior to boarding Said it was fixed, we boarded Waited Then learned it was not fixed Had to deplane and go to new gate Bought wifi on plane and it never worked

2.0 MediocreJames, Aug 2026
Read more Delta reviews

They announced a mechanical issue prior to boarding Said it was fixed, we boarded Waited Then learned it was not fixed Had to deplane and go to new gate Bought wifi on plane and it never worked

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.

Delta off boarded and boarded the aircraft quickly. Clean cabin and great gate and onboard service.

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

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.

I upgraded to first. Quick and easy boarding. Comfortable seat with power and a nice IPA.

Flight was delayed due to needing a replacement flight crew. Delta changed the aircraft type in Detroit. One hour delay. But once in the air, good flight

The flight was excellent. Their was no service as we boarded, the flight attendants spent about 30 minutes just taking and not really caring that the cabin was about 80 degrees and did not offered any beverage to first class passengers or any passenger. The flight from DEN to ONT is not long but not under an hour, we received one drink and bag of chips if you were lucky. I was in first class…. I did leave my hat on the plane and it only took less than five minutes for a United rep to locate and bring it to me.

Bad check in experience. Dirty ancient aircraft. Truly awful food and this in Business/ First class.

I truely appreciate all services. I was highly impressed and will not hesitate to recommend United Airlines to friends and family. The AVML was perfect.

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.

ok, butt flght was delyed for 2,5h from Frankfurt, and next Flight to Columbuse same

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

Tired of being nickel and dimed for every little thing, especially carry-on luggage.

Late start, late arrival and very uncomfortable seats. No legroom, no elbow room because the person next to me was fat. I had to press myself toward the aisle or be rubbing arms with them. As a result, I was bumped every time someone passed in the aisle. But I couldn't get away from the hip encroachment. Who wants to rub hips with an oversized stranger for over 2 hours? I'm not fat, just tall and larger-than-average frame so I need to leg room but it would be nice if other peoples' body parts weren't squeezing under and over the arm of the seating. Why should it cost me so much for simple comfort so United can get a little more profit?

Not good always. Even our trip to japan was disaster with the American airlines delays and cancellatios. Now unfortunately we needed to book again with them last min. Was okay but as usual not comfortable seating.

If the service crew didn't make difference between people and they change my seat without asking me if is okay or not with me

Great for a small Commuter. Quiet and relaxing. Seats were better than most.

The plane was late getting to Ontario by half an hour which makes it inconvenient when you have people waiting for you.

boarding sucked they lost my bag never flying Iberia again

Disorganized boarding. Mandatory to gate check bags. Curt flight staff. No space for cabin bag, even when I was in first class.

Like all of the flights I took to get down to Dallas. They were delayed

They are still charging me after taking 466 and 833 for round trip from AR to to Bradley airport from 19 to 21. Then poor experience. Am hurt and I will say it on social media. Please stay away from this airline. I see in my bank account they are still taking 644. Am trying to stop it. I used to fly United airlines and I suggest that if you don't want extra charges and good service you go back there. American airlines delayed my flight again and I was late for my meeting, no recompensation but charging me over and over.

Good communication at the gate and very nice crew in the flight

Unfortunately we had turbulence because of the weather and when we were about to land in Miami, the pilot brought the aircraft quickly up because another plane was in its way. The pilot was remarkable however we weren’t told until we started our second descent. Our flight was GOOD. The flight from Miami to Hartford was packed, so many people. It was late at night and we were tired and just wanted to be home. Obviously, the aviation staff preformed well.

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.

Check in and passport control were seamless and efficient. Plenty of room in overhead bins. Our original seats were separate but crew at the gate put us together in finer seats. I also had left my phone on board and the Jet Blue staff were so helpful in retrieving it after I had left the baggage area

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.

Not having an assigned seat until boarding and then having to check my bag.

Cancelled flight with no specific instructions to get a boarding pass for another flight. The whole flight of people were in line for an hour because there was only 1 person to help at the desk. This was unusual for JetBlue.

When I was boarding my departure from Raleigh to Orlando I was inappropriately scolded by a female dog named Mia because I didn’t pay in advance for my carry on bag ($75). Frontiers website is confusing regarding pre-paying for carryons so it was a simple mistake. I also had paid for “upfront plus” meaning me and my son were seated in the front row with no one in the middle seat ($450 upgrade). When we were boarding Mia said “sir, you didn’t pay for your carryon” in a not so polite tone and told me to get out of line and come back to the counter to pay for my carryon. The way they had the retractable rope left me no room to circle back without making the people behind me move so I just stood there and then she said a second time “sir!! Go pay for your carryon” in an embarrassing tone. I then moved their rope so I could get back to the counter when a second female dog then asked “are you done!?!?” because I had said “do you want me to bulldoze the people behind me?” I then said you do realize I paid over $400 for upfront plus so I was certainly not trying to sneak a carryon bag without paying. Long story short, I am soooo done with discount airlines!!! By the time you pay for all the “extras” you might as well have paid for Delta Southwest or American! Frontier airlines sucks and I was embarrassed by a female dog named Mia!!!

Frontier is good until they cancel your flight. Way too many cancellations.

I know Frontier is a “no-frills” airline. I understand the concept. However, I jumped on some tickets for our family vacation, expecting to play a bit of a game to figure out the family bags and not over spend. In the end, I got the short end of this deal by far. 1. I did not expect them to charge the baggage fee for each direction. It makes the fee look high-ish at a glance, but reasonable. Then when you get to checkout and realize you have to pay it twice to come home with your luggage, it becomes ridiculous. 2. The low checked bag weight limit. I am used to packing a 50lb bag with my preferred airline. Frontier’s artificially low 40lb limit more quickly triggers the extra weight fee, which almost DOUBLES the price of the bag if you go over ($79 for the bag/$75 for the next 10 lbs) 3. The fee for a carry-on bag is the same as a checked bag but with a lower size and weight limit. Make it make sense! 4. The seats are terrible. My 2.5 hour flight almost had me losing my mind. I’m 6’3” and my femurs barely fit in the space provided. My knees had to wiggle just right to jam into the crack next to the armrest of the seat in front of me. The cushioning was thin and inadequate. I am tall but I’m not a freak. These seats are unacceptable. 5. I overheard the woman next to me speaking with the gate agent about being charged a $25 fee for not checking in online - she checked in at the airport counter when she arrived. That’s ridiculous. She was old and in a wheelchair. She had a paper boarding pass, and was obviously not tech savvy. She should not be punished for that. 6. They do not have good placement in the terminals. It was always out on the end or down on a subfloor, and we had to walk out on the tarmac almost every time. In Denver. Their home airport! 7. Every time I loaded a new page on the website while buying my tickets or my bags, it was constantly trying to upsell me on some esoteric bundle. Like, a pop-up every time. Very annoying. 8. No screens in the boarding area (at least where we were) to confirm you’re in the right place. Just static gate number signs. I am sure these are standard practices for Frontier, and I should have read more about them before I purchased tickets, but as a result of this single round trip, I do not plan to ever use this cut-rate airline again. I would rather pay the normal amount for a ticket and be treated like a customer instead of a mark.

Our flight was delayed 2 hours and when they changed the the time to 1 hour I wasn't alerted and when I checked the gate the plane was still there but they already shut the doors so I had to buy another flight.

Don’t even matter if I write it y'all not going to fix it

Great except upon arrival it took them a long time to open the doors

Frontier feels like a family I Worked for Eastern Airlines back in the day and I felt the family vibe that I had then. Thank you

Terrible. Delayed my family flight for several hours affecting family plans

Tiny seats, no entertainment, no amenities, delays, they charge for carry on and their allowed personal item is smaller than in other airlines.

Pro: The stuff was great. Friendly, patient and caring. Our seat row was clean. The bath room was clean. Our flights were close to on time. Con: The leg room is too small. No blankets or pillows. No entertainment devices at all. I can’t remember to have a food choice. I would fly again with frontier for short distances.

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