$138 Find Cheap Flights from Rochester 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 Rochester to Caribbean Islands departing on 5/5. 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
1 adult, Economy, 0 bags

KAYAK searches 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 Rochester to Caribbean Islands, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Rochester to Caribbean Islands, as well as popular online travel agencies
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Cheap Flights from Rochester to Caribbean Islands

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Punta Cana
Punta Cana2 stops$532
Montego Bay
Montego Bay1 stop$422
Kingston
Kingston2 stops$708
Punta Cana
Punta Cana2 stops$532
Montego Bay
Montego Bay1 stop$422
Kingston
Kingston2 stops$708

Book Cheap Rochester to Caribbean Islands 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 Islands 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 Islands

Sat, May 9 - Wed, May 13
American Airlines Logo
7:18 pm - 3:35 pm
RST
-
SJU
19h 17m
2 stops
American Airlines Logo
7:25 am - 11:55 pm
SJU
-
RST
17h 30m
2 stops
$250American Airlines
Sat, May 9 - Wed, May 13
American Airlines Logo
7:18 pm - 2:18 pm
RST
-
SJU
18h 00m
1 stop
American Airlines Logo
7:25 am - 11:55 pm
SJU
-
RST
17h 30m
2 stops
$300American Airlines
Sat, May 9 - Wed, May 13
American Airlines Logo
7:18 pm - 2:18 pm
RST
-
SJU
18h 00m
1 stop
American Airlines Logo
7:25 am - 11:55 pm
SJU
-
RST
17h 30m
2 stops
$317American Airlines
Sat, May 9 - Wed, May 13
United Airlines Logo
11:05 am - 8:34 pm
RST
-
SJU
8h 29m
1 stop
United Airlines Logo
3:56 pm - 12:36 am
SJU
-
RST
9h 40m
1 stop
$324United Airlines
Sat, May 9 - Wed, May 13
American Airlines Logo
5:40 am - 10:05 pm
RST
-
SJU
15h 25m
2 stops
American Airlines Logo
4:30 pm - 11:06 am
SJU
-
RST
19h 36m
2 stops
$326American Airlines
Sat, May 9 - Wed, May 13
American Airlines Logo
7:18 pm - 2:18 pm
RST
-
SJU
18h 00m
1 stop
American Airlines Logo
7:25 am - 11:55 pm
SJU
-
RST
17h 30m
2 stops
$350American Airlines
Sat, May 9 - Wed, May 13
American Airlines Logo
7:18 pm - 2:18 pm
RST
-
SJU
18h 00m
1 stop
American Airlines Logo
4:30 pm - 11:06 am
SJU
-
RST
19h 36m
2 stops
$366American Airlines
Mon, May 4 - Thu, May 7
United Airlines Logo
5:00 am - 2:44 pm
RST
-
SJU
8h 44m
1 stop
United Airlines Logo
7:20 am - 9:44 pm
SJU
-
RST
15h 24m
2 stops
$390United Airlines
Tue, Apr 14 - Sat, Apr 18
American Airlines Logo
5:40 am - 10:05 pm
RST
-
SJU
15h 25m
2 stops
American Airlines Logo
5:45 am - 11:55 pm
SJU
-
RST
19h 10m
2 stops
$399American Airlines
Tue, Apr 14 - Sat, Apr 18
American Airlines Logo
5:40 am - 8:51 pm
RST
-
SJU
14h 11m
2 stops
American Airlines Logo
5:45 am - 11:55 pm
SJU
-
RST
19h 10m
2 stops
$401American Airlines
Booking Insights

KAYAK's insights & trends for Rochester to Caribbean Islands flights

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

Can I save money by flying with a layover from Rochester to Caribbean Islands?

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

No, with an average price for the route of $308, prices are generally cheapest when you fly direct.

Find deals

Good to know

Low seasonJuly
Best time to beat the crowds with an average 9% drop in price.
Most popular time to fly and prices are also 23% lower on average.

FAQs - booking Caribbean Islands flights

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

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Rochester 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 Rochester 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 Rochester 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 Rochester 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 Rochester to Caribbean Islands up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Reviews of the top airline flying from Rochester to Caribbean Islands

 
See real verified KAYAK customer reviews for airlines flying from Rochester 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 Rochester 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.
7.1
American AirlinesOverall score based on 11488 reviews
7.2Comfort
7.5Boarding
6.4Food
6.9Entertainment
7.9Crew
Airline reviews

Absolutely terrible. Would never fly American again. 2 deplaned incidents and delayed by close to 24 hours. $12 meal voucher for first class passengers was an insult to the injury. Pathetic.

2.0 MediocreSaurabh, Mar 2026
DFW - EWR
Read more American Airlines reviews

Absolutely terrible. Would never fly American again. 2 deplaned incidents and delayed by close to 24 hours. $12 meal voucher for first class passengers was an insult to the injury. Pathetic.

Terrible planning. And even worse gate agents. Absolutely rude behavior.

Half of the TSA checkpoints at PHL are closed. Also, there is no standby for first class passengers. You can only standby for coach. Very dated policy and inconsistent with peers.

Flight was scheduled at 11:26am but they keep Delaying until midnight. They waited at airport restless.

Rough flight No beverage service due to turbulence Bottom Seat cushion was non existent

Great experience. Good dinner and service. FA's were very nice and attentive.

It was great. Smooth flight, comfortable, left on time and landed on time.

Perhaps this is an airport issue, but being in a takeoff queue for over an hour in the taxiing lane is unacceptable. We will definitely be seeking alternative avenues for air travel in the future.

We hoarded. Then we deplaned. Then we waited for 10 hours in the MSP airport due to a wheel misfunction. We understand safety but communication between crew and airport staff was horrible. When we did finally board, we were rushed on and because we were waiting for a “fresh” pilot and crew, we sat in a roasting plane with no A/C for an hour. My question is why was this flight not cancelled right away when they knew this would be a huge issue OR, why did AA not get a substitute plane, considering this was already a full flight? To me, this appears to be a complete breakdown in leadership and utter systems failure. The compensation for completely disrupting travel plans for hundreds, which we paid dearly for, was measly. While we appreciated the lodging for the night, $12 in meal vouchers isn’t going to sustain anyone for over 12 hours. “We apologize; our hands are tied” is no longer an acceptable explanation. We are so completely turned off by this experience and will definitely seek alternative avenues when we need to fly.

Mostly good. The WiFi wasn’t working so that was not great.

Everything you need to know for your flight to Caribbean Islands

Information on your arrival and departure airports

Rochester (RST)