$128 Find Cheap Flights from Rochester to Caribbean - 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 Rochester to Caribbean departing on 9/9. 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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Cheap Flights from Rochester to Caribbean

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Punta Cana
Punta Cana1 stop$390
Santo Domingo
Santo Domingo1 stop$426
Montego Bay
Montego Bay1 stop$329
Oranjestad
Oranjestad2 stops$466
Nassau
Nassau1 stop$360
Kingston
Kingston1 stop$456
Simpson Bay
Simpson Bay2 stops$402
Providenciales
Providenciales1 stop$463
Bridgetown
Bridgetown2 stops$609
George Town
George Town1 stop$357
Willemstad
Willemstad1 stop$547
Aguadilla
Aguadilla1 stop$416
Puerto Plata
Puerto Plata1 stop$690
St. John's
St. John's1 stop$560
Punta Cana
Punta Cana1 stop$390
Santo Domingo
Santo Domingo1 stop$426
Montego Bay
Montego Bay1 stop$329
Oranjestad
Oranjestad2 stops$466
Nassau
Nassau1 stop$360
Kingston
Kingston1 stop$456
Simpson Bay
Simpson Bay2 stops$402
Providenciales
Providenciales1 stop$463
Bridgetown
Bridgetown2 stops$609
George Town
George Town1 stop$357
Willemstad
Willemstad1 stop$547
Aguadilla
Aguadilla1 stop$416
Puerto Plata
Puerto Plata1 stop$690
St. John's
St. John's1 stop$560

Book Cheap Rochester to Caribbean Plane Tickets

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Rochester to Caribbean 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 Rochester to Caribbean

Wed, Sep 30 - Sat, Oct 17
Multiple Airlines Logo
7:05 pm - 11:57 pm
ROC
-
SJU
28h 52m
1 stop
Multiple Airlines Logo
5:12 pm - 7:33 pm
SJU
-
ROC
26h 21m
1 stop
$262Multiple Airlines
Thu, Oct 8 - Wed, Oct 14
Multiple Airlines Logo
7:53 pm - 11:38 pm
ROC
-
SJU
27h 45m
1 stop
Multiple Airlines Logo
5:12 pm - 7:03 pm
SJU
-
ROC
25h 51m
1 stop
$271Multiple Airlines
Sat, Oct 24 - Thu, Oct 29
American Airlines Logo
7:36 pm - 2:55 pm
ROC
-
STT
19h 19m
2 stops
American Airlines Logo
3:46 pm - 10:20 am
STT
-
ROC
18h 34m
2 stops
$280American Airlines
Tue, Oct 6 - Sat, Oct 17
United Airlines Logo
6:20 am - 8:38 pm
ROC
-
SJU
14h 18m
2 stops
United Airlines Logo
4:55 pm - 11:44 pm
SJU
-
ROC
6h 49m
1 stop
$296United Airlines
Sat, Nov 7 - Fri, Nov 13
United Airlines Logo
6:30 am - 3:40 pm
ROC
-
SJU
8h 10m
1 stop
United Airlines Logo
2:05 am - 1:27 pm
SJU
-
ROC
12h 22m
2 stops
$302United Airlines
Wed, Oct 21 - Mon, Oct 26
Delta Logo
5:30 am - 11:25 am
ROC
-
MBJ
6h 55m
1 stop
Delta Logo
12:50 pm - 12:33 am
MBJ
-
ROC
10h 43m
1 stop
$352Delta
Fri, Oct 2 - Thu, Oct 29
Delta Logo
6:20 pm - 1:01 pm
ROC
-
MBJ
19h 41m
2 stops
Delta Logo
1:32 pm - 10:46 pm
MBJ
-
ROC
8h 14m
2 stops
$357Delta
Sat, Oct 24 - Sat, Oct 31
American Airlines Logo
7:36 pm - 12:58 pm
ROC
-
STT
17h 22m
2 stops
American Airlines Logo
3:46 pm - 12:02 pm
STT
-
ROC
20h 16m
2 stops
$359American Airlines
Sun, Aug 30 - Thu, Sep 3
JetBlue Logo
6:38 am - 1:54 pm
ROC
-
SXM
7h 16m
1 stop
JetBlue Logo
11:20 am - 12:04 am
SXM
-
ROC
12h 44m
1 stop
$517JetBlue
Fri, Sep 11 - Thu, Sep 17
JetBlue Logo
7:10 am - 3:30 pm
ROC
-
AUA
8h 20m
1 stop
JetBlue Logo
1:40 pm - 11:31 pm
AUA
-
ROC
9h 51m
1 stop
$531JetBlue
Booking Insights

KAYAK's insights & trends for Rochester to Caribbean flights

Get data-powered insights and trends into flights from Rochester to Caribbean to help you find the cheapest flights, the best time to fly and much more.

What is the cheapest month to fly from Rochester to Caribbean?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Rochester to Caribbean, 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 Rochester to Caribbean is January, when tickets cost $423 (return) on average. On the other hand, the most expensive months are December and June, when the average cost of round-trip tickets is $588 and $571 respectively.

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

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from Rochester to Caribbean, 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 Rochester to Caribbean, you should book around 3 weeks before departure, which saves you about 16% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 8 weeks before departure.

Good to know

Low season

September

Cheapest flight

$128
Best time to beat the crowds with an average 11% drop in price.
Flight from Rochester to San Juan

FAQs - booking Caribbean flights

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

    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 Rochester to Caribbean.

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

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

    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 Rochester to Caribbean 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 Rochester to Caribbean?

    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 Rochester to 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 Rochester to Caribbean

 
Need help choosing which airline to fly with from Rochester to Caribbean? 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 4241 reviews
7.0Food
8.1Boarding
7.5Entertainment
8.0Comfort
8.6Crew
Airline reviews

Flight coming out of Buffalo was delayed, so we had to be rescheduled on another flight from Baltimore to Phoenix which means we had a long layover and got home 3.5 hours late. Shuttle to parking stopped at 10pm, so we had to pay for an Uber to the parking lot and got charged an extra day of parking since it was after midnight. Not the best experience. Long day!

2.0 MediocreDawn, Jun 2026
BUF - BWI
Read more Southwest reviews

Flight coming out of Buffalo was delayed, so we had to be rescheduled on another flight from Baltimore to Phoenix which means we had a long layover and got home 3.5 hours late. Shuttle to parking stopped at 10pm, so we had to pay for an Uber to the parking lot and got charged an extra day of parking since it was after midnight. Not the best experience. Long day!

We had a 5 hour delay on the tarmac in Baltimore

Airline travel is always too cramped to really be pleasant, but the cabin crew on this flight did a pretty good job of making up for it by putting on some music during boarding and sprinkling a few funny remarks into the safety briefing and announcements, and just generally being friendly and helpful. It definitely reminded me of why I prefer the in-flight experience on Southwest!

Flight was delayed due to plane not passing inspection And one of the crew had to time out and we had to wait for another one A 3 hour delay

It was one and half hour late... Not sure if any other experience matters.

It was 2 hours 45 minutes late, for no apparently clear reason.

It went well. Plane wasn't full. Will be great when assigned seating is in place

My bag was damaged and is now missing a wheel. I tried to buy a claim in on the website but it would not accept my confirmation # for submission. Other than that, everything else was good!

As always it was a pleasure to fly on southwest.

Excellent! There was a delay due to the weather and they did all they could do to keep us comfortable & updated. Thank you!

Flight delayed due to ground hold. Republic airways did a great job.

Our flight was delayed multiple times and then canceled at almost 1 in the morning. We are a family of 7, traveling with 5 young children. When the flight we were supposed to fly on finally arrived after waiting all day after an international flight into JFK we were informed our flight was in need of a copilot and once they located one we would take off. Then our flight was cancelled because the copilot was over his hours and they couldn't locate another. They knew before taking off from the previous location that the copilot would be unable to fly. They could have communicated the cancellation of the flight hours in advance. Once they cancelled and the pilot and copilot got off the flight, they joked about it. While there are understandably limits on flight time for pilots, they can still handle the situation in a professional manner. The late cancellation resulted in angry passengers that required police intervention in the airport. It also occurred so late and included other delta flights that after trying 15 different hotels, we were unable to secure a hotel room, they were all booked. No rental cars were available in the area either. We ended up staying in the airport with the 5 children. We made it home after 54 hours of travel with maybe 2 hours of sleep. Our luggage was lost and had to be claimed at the airport at our final destination. This was the worst trip I have ever taken and the worst airport I have ever spent time in. I met two individuals in the airport that were kind and helpful; Tonya Maingot Williams from the can we hel desk that worked to help get us rebooked and home, as well as provide us with care bags for our extended stay in the airport. The other individual was Danielle from Buffalo Wild Wings that was so very kind when we found a place to take our family we were traveling with to eat, all 11 of us and we were able to sit down together to enjoy a meal during such a stressful time.

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

Third flight in two months where the crew was not there. Comfort seating does not guarantee overhead bin space. Passengers with children are allowed on the plane first - if you are flying to and from Orlando, this means half the plane has boarded before you get on. And somehow all the bin space is taken up. 3 out of 5 flights have had issues with equipment or procedure. Some of these instances caused the flight to be delayed because of a "nuisance" light. One time it was a bag that had been brought on board but did not belong to anyone so we had to return to the gate. Last night we were told the "AC" on the plane doesn't work well and we're 10th for take off- because the crew was late - and that it will get cool when we're in the air. Not sure if this is usual, but I didn't think flight crew could jump seat in first class. Movie and TV selection has not been refreshed for several months- flying one to two round trips each month easily exhausts the list of content.

Great experience nice pilot very soft and easy landing and take off

Flight was delayed before take off and at landing. Baggage took 20 minutes. Flight crew would not serve full soft drink and had to ask multiple times before receiving water.

On time! There were plenty of airport employees who were able to keep us moving in the right direction. The crew on the plane were professional.

I continue to be satisfied with Delta’s excellent service out of LGA. The digit id works well and gets me through security in no time. Whenever possible, I choose Delta.

We just spent $6000 on our first trip since pre COVID and we were stranded on the runway of our departing airport for 2 hours and 15 minutes while our layover was only an hour and a half. We were told by the pilot we were next for de-icing and then got bumped by 3 other planes. Pilot went on to say they only had one guy working the de-icing where they usually have at least 2. In Rochester. In the heart of winter. Someone missed a step and should be fired. I'm not done.

We liked the friendliness of the crew -I know short trip but like the Monitors on the 🚢

The seats on this flight weren’t as comfortable as we had expected. Even leaned back these seats left us feeling crappy in our backs. Also we had to use our own tablets for movies, but nothing in the seats in front of us to hold the tablets up.

Check in was chaotic with only one counter for business class and first class. The luggage conveyor belt at JFK airport was broken so the flight departure was delayed which made the flight stressful as I had a tight connection. Although the captain said they could make up the delay, they didn’t do so.

I had a good time. However, I paid for the wifi and it was in and out the whole flight.

3 hour delay…. Nearly 2 hours sitting on tarmac. Do better, United. Or at least have the sense to not say “we hope you enjoyed your flight with us” upon disembarking.

Everything except the food and entertainment. It was a great experience though

Unfortunately weather delayed our flight waiting for our plane to arrive and due to a little snow time was needed to deice the plane so departure was very delayed and I missed the connecting flight

Flight was delayed from 35 minute delayed aircraft arrival to 90 minute delay causing us to miss international connecting flight on SWISS resulting in 16 hour delay to reach detonation causing significant angst, monetary loss and discomfort. SWISS transfer desk and staff was like robots not willing to help at all.

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.

The staff was very friendly. The seats seemed quite small. Overall the flight was pleasant.

Crew and agents misguiding on tight connections, and lack of connecting crew looking for inbound planes. A very avoidable missed connection as a result.

I don’t like the music section but I believe it was a cost decision. I changed my flight last minute due to work issues and had to sit way in the back. The seats were way closer together than I would have preferred.

Our particular exceptional experience was with Johnny at JFK at check in. He was the kindest, most accommodating agent I’ve ever encountered taking extra steps to help my husband and I with our extra baggage. I hope that he knows how much he positively affected our trip.

The flight attendant was very polite and attentive. The food was good.

The flight de-boarded after being informed of a 3 hour delay. The gate agent said we could go to lounge. The flight ended up boarding 20 minutes later and I missed it.

My experience with American Airlines was great. Unfortunately my stroller was not located and has not been given to me and or reached out in return for in regard to information.

Pilots were fantastic - super smooth. First Class flight attendant was very attentive. Main Cabin flight attendant should try to smooth the rough edges of her voice - very shrill / punitive. Hurt my ears just to listen to her. Recognize they have a (tough) job to do - but tone over speakers needs to be less like scolding a 5 year old.

Maybe focus more on delivering a good product vs selling me a damn credit card

Tell the crew (when boarding) to yell at the imbeciles blocking us from walking up to scan. I promise everyone crowds around and half of us (most the time I’m group 4) have to push our way through. Your staff is awesome, the public - not so much-

Due to an issue with the plane. We waited almost 2 hours to take off. The service reps were great. We had a longer layover but was able to run for it and catch our flight. This also happened on our way out. Maybe the planes need a good look over. The people who work front desk and flight attendants are the best

The flight was delayed. I upgraded to more room. I can't imagine how small the regular seats are I haven't upgraded for my return flight yet.

see my previous response about being kicked off the flight and having to fly the next day, ruining a planned vacation tour.

It was a smooth flight and the pilot was very pleasant

Flight was cancelled, no support at JFK even though it is their main hub.. wait times on the phone was very long

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

Domestic flights are good. Just stay away from international travel

First the flt was delayed over 2 hrs bc of plane mechanics that should have been handled better! No text or email was sent so only found out at the airport so there we sat for 5 hours! THATS RIDICULOUS! The gate area was filthy! No agents showed up till hr before so no additional info was given-waited online for 15 mins while the gate agent chatted and got together then given last seat in back of plane!! No priority for senior or anything-took attendants over 2hrs to serve drinks and snack-WHY are they not served together? By time snack came needed another drink! Worst service in my life!

Since we started at syr the service, crews, and flights were just excellent

All the TV screens in my rows was non functional . The map shown for an international route was antiqued..

JetBlue was good. Kayak offered us a deal if we bundled the rental car. This was a complete scam. Kayak said the total was $222... but when we went to pick up the car the agent at Rent a wreck said that we had to pay "fees and taxes" for a grand total of $750. I would recommend not using kayak or rent a wreck. They are both complicit in this scam. JetBlue worked out well.

Everything you need to know for your flight to Caribbean

Information on your arrival and departure airports