$168 Find Cheap Flights from Denver 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 Denver to Caribbean Islands departing on 8/29. 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 Denver to Caribbean Islands.
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Denver to Caribbean Islands.
Travelers love KAYAK
41,299,237 searches in the past 7 days on KAYAK

Save 21% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Bundle and saveSave money when you bundle your flight + hotel.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Flight Deals
Booking Insights
Flight Deals

Cheap Flights from Denver to Caribbean Islands

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Punta Cana
Punta Cana1 stop$425
Santo Domingo
Santo Domingo1 stop$510
Montego Bay
Montego Bay1 stop$509
Oranjestad
Oranjestad1 stop$491
Nassau
Nassau1 stop$423
Kingston
Kingston1 stop$434
Simpson Bay
Simpson Bay1 stop$540
Providenciales
Providenciales1 stop$487
Port of Spain
Port of Spain2 stops$521
Bridgetown
Bridgetown1 stop$468
George Town
George Town1 stop$396
Willemstad
Willemstad1 stop$565
Castries
Castries2 stops$918
Aguadilla
Aguadilla1 stop$396
Puerto Plata
Puerto Plata1 stop$684
St. John's
St. John's1 stop$555
Punta Cana
Punta Cana1 stop$425
Santo Domingo
Santo Domingo1 stop$510
Montego Bay
Montego Bay1 stop$509
Oranjestad
Oranjestad1 stop$491
Nassau
Nassau1 stop$423
Kingston
Kingston1 stop$434
Simpson Bay
Simpson Bay1 stop$540
Providenciales
Providenciales1 stop$487
Port of Spain
Port of Spain2 stops$521
Bridgetown
Bridgetown1 stop$468
George Town
George Town1 stop$396
Willemstad
Willemstad1 stop$565
Castries
Castries2 stops$918
Aguadilla
Aguadilla1 stop$396
Puerto Plata
Puerto Plata1 stop$684
St. John's
St. John's1 stop$555

Book Cheap Denver 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 Denver 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 Denver to Caribbean Islands

Mon, Aug 17 - Mon, Aug 31
Frontier Logo
5:05 pm - 6:26 am
DEN
-
SJU
11h 21m
1 stop
Frontier Logo
6:41 pm - 8:37 am
SJU
-
DEN
15h 56m
1 stop
$353Frontier
Tue, Aug 4 - Mon, Aug 10
Frontier Logo
11:40 pm - 12:23 am
DEN
-
SJU
22h 43m
2 stops
Frontier Logo
7:10 am - 8:20 am
SJU
-
DEN
27h 10m
1 stop
$371Frontier
Tue, Aug 25 - Sun, Aug 30
Multiple Airlines Logo
5:15 pm - 6:26 am
DEN
-
SJU
11h 11m
1 stop
Multiple Airlines Logo
6:00 am - 2:30 pm
SJU
-
DEN
34h 30m
2 stops
$372Multiple Airlines
Thu, Aug 6 - Sat, Aug 15
Multiple Airlines Logo
11:59 pm - 12:41 am
DEN
-
SJU
22h 42m
1 stop
Multiple Airlines Logo
6:00 am - 8:21 am
SJU
-
DEN
28h 21m
2 stops
$375Multiple Airlines
Wed, Aug 5 - Thu, Aug 13
Southwest Logo
6:15 pm - 9:10 am
DEN
-
SJU
12h 55m
1 stop
Southwest Logo
8:55 pm - 8:15 am
SJU
-
DEN
13h 20m
1 stop
$376Southwest
Sun, Jul 12 - Thu, Jul 23
Southwest Logo
11:50 pm - 2:30 pm
DEN
-
PUJ
12h 40m
1 stop
Southwest Logo
4:55 pm - 11:45 pm
PUJ
-
DEN
8h 50m
1 stop
$425Southwest
Wed, Jun 17 - Wed, Jun 24
JetBlue Logo
11:59 pm - 3:23 pm
DEN
-
AUA
13h 24m
1 stop
JetBlue Logo
1:35 pm - 10:59 pm
AUA
-
DEN
11h 24m
1 stop
$492JetBlue
Mon, Aug 17 - Tue, Aug 25
JetBlue Logo
11:37 pm - 2:03 pm
DEN
-
STT
12h 26m
1 stop
JetBlue Logo
2:58 pm - 9:34 am
STT
-
DEN
20h 36m
2 stops
$545JetBlue
Sun, Oct 18 - Sun, Oct 25
American Airlines Logo
6:59 pm - 10:40 am
DEN
-
STT
13h 41m
2 stops
American Airlines Logo
5:40 pm - 11:24 am
STT
-
DEN
19h 44m
2 stops
$660American Airlines
Tue, Nov 3 - Wed, Nov 11
American Airlines Logo
12:20 am - 3:15 pm
DEN
-
STT
11h 55m
1 stop
American Airlines Logo
4:18 pm - 9:48 pm
STT
-
DEN
8h 30m
1 stop
$665American Airlines
Booking Insights

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

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

What is the cheapest Denver to Caribbean Islands flight route?

Data is based on round-trip flight searches on KAYAK over the past month.

The cheapest ticket to Caribbean Islands from Denver found in the last 5 days was to San Juan, at $577 round-trip. The most popular route is from Denver (DEN) to San Juan Luis Munoz Marin Intl Airport (SJU), and the cheapest round-trip airline ticket found on this route in the last 5 days was $577.

What is the cheapest time of day to fly to Caribbean Islands?

The average price for all round-trip flights from Denver to Caribbean Islands depending on the time of departure, clicked by users on KAYAK in the last 2 weeks.

The cheapest time of day to fly to Caribbean Islands is generally in the morning, when round-trip flights cost $699 on average. The most expensive time of day to fly to Caribbean Islands is generally in the morning, which is peak travel time and where the average cost of a ticket is $699.

Can I save money by flying with a layover from Denver 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 $436, prices are generally cheapest when you fly direct.

What is the cheapest month to fly from Denver to Caribbean Islands?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Denver to Caribbean Islands, 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 Denver to Caribbean Islands is April, when tickets cost $120 (return) on average. On the other hand, the most expensive months are February and December, when the average cost of round-trip tickets is $2,754 and $2,139 respectively.

What’s the cheapest day of the week to fly from Denver to Caribbean Islands?

The average price of all round-trip flights from Denver to Caribbean Islands clicked on KAYAK for each day over the last 12 months.

If you are looking for a flight deal from Denver to Caribbean Islands, look for departures on Tuesdays and avoid leaving on a Friday, as it's usually the priciest day. When flying back from Caribbean Islands, Thursday is the cheapest day to fly and Sunday is the most expensive.

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

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from Denver to Caribbean Islands, 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 Denver to Caribbean Islands, you should book around 1 week before departure. For the absolute cheapest price, our data suggests you should book 2 weeks before departure.

Good to know

Low seasonSeptember
Cheapest flight$168
Best time to beat the crowds with an average 7% drop in price.
Most popular time to fly with an average 6% increase in price.
Flight from Denver to San Juan

FAQs - booking Caribbean Islands flights

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

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Denver 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 Denver 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 Denver 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 Denver 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 Denver 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 5 airlines serving from Denver to Caribbean Islands

 
See real verified KAYAK customer reviews for airlines flying from Denver 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 Denver 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.
7.9
SouthwestOverall score based on 4235 reviews
7.5Entertainment
8.6Crew
8.0Comfort
8.1Boarding
7.0Food
Airline reviews

there were two flight attendants that were up front...that were the best! They get KUDOs for making my trip only fantastic. Tell them Jeff said that!

10.0 ExcellentAnonymous, Jun 2026
OKC - LAS
Read more Southwest reviews

there were two flight attendants that were up front...that were the best! They get KUDOs for making my trip only fantastic. Tell them Jeff said that!

OKay. I sat in the back of the plane and it was really loud between babies and little kids, and adults who.like to talk a lot and loudly most of the flight.

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!

Was fine, delayed and feels like southwest is always late

I don't know why flying out of Sarasota requires two plane changes.

The first time I flew in the extra legroom section. It was difficult to notice a difference. I had bad luck with my neighbors. The crew was okay. Southwest has reduced the live TV options.

The flight was smooth. The Southwest experience has degraded overall, but this one was okay.

No gluten free snacks. Seats felt worn or bare bones even though it was a new 737 MAX 8.

One major problem that was very unprofessional and uncalled for. Plane landed and we had to wait 20 minutes to get off the plane since they were waiting for someone to come to the gate to drive the jetway. Southwest couldn't have someone available and waiting for the plane to land? Is there only one person in Hobby airport who knows to drive the jetway? Was he at lunch? In the bar? Uncomfortable and uncalled for!

The checking experience in Orlando was terrible, almost missed the flight. Too many travelers and Southwest completely understaffed.

Long story short, it was one of the better flight experiences I've had in some time when compared with other airlines.

Flight was great! This flight from Atlanta was even better than when I paid for Comfort from SNA to Atlanta.

Connection flights should be spaced out farther because too close I missed my connection.

Definitely a southern flavor. Cordiality was evident even though no drinks or snacks were served.

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.

Left /arrived on time. Decent seat space. Like the wifi/plugs and entertainment. Windows and tray table were kinda gross. Attendants didn't start snack service til 40mins before landing. Two rows before us, captain came on to say there's turbulence and recalled staff to seats. So, no drink/snack. Later, attendants didn't stop to see if we had trash nor even look our way. Felt invisible! Almost all pilot announcements were not only unintelligible, but so quiet. We had no idea what she said.

Average seat comfort, a drink and chips were provided, early boarding because we checked a carryon at the gate was nice. Ticket pricing shenanigans, including fees to pick a seat, check a bag, and get food onboard - evidence the industry is reinvigorating last century’s strategies- destroys the experience before one ever arrives at the airport. It’s difficult to recognize any value or sustain loyalty in the end-to-end process making air travel more drudgery than pleasure.

Gate agent was unhelpful for handicapped boarding. Flight attendant seemed untrained.

No service flight that took 5 hrs and a stop at an unscheduled airport. Crew and pilots did their jobs

Clean planes and not take my comfort class seat away.

Destroyed my suitcase. Tired of talking about it. Cancelling my unite mileage plus account.

New plane was lovely. Crew customer service is always lax but expected. Kraft on time and arrived safely.

It was a short flight so I was expecting too much

Had a one hour delay due to mechanical issue. I didn’t think I’d be able to make my connecting flight, but they waited for me and greeted me when I arrived to help things run smooth.

O’hsre taxi and deboarding took 40 minutes. Needed 20 minutes extra time between connecting flights to avoid running through terminal.

Was great in general, try to respect time and excuses when slight changes have been made, appreciated!

Really hard landing... as in slammed into the runway then hit the brakes really hard ...

Putting people that close to the bathroom, where you have to look into the bathroom as people are exiting and entering was not great and the smell was also not great. I know the airlines are desperate for more chairs, but that seat is a crime.

Every staff member was professional, friendly and courteous. The pizza twist was ok. It was warm but too much dough.

one staffer was frustrated (it happen); the flight was late and the pilot mentioned they'll make amend but the snacks were the same, other than that the aircraft was clean and everything went smooth, no complaints

Our flight from JFK to Madrid was delayed. We had to go from one side of the Madrid airport (Terminal 4s to the far end of terminal 4 - Gate K98) to our gate in less than 30 minutes. Put passport control and security/baggage check and that’s very hard unless you’re Usain Bolt. I called Iberia Airlines and the telephone customer service told me that I was going to have to pay to re-book. Luckily the help desk in the airport (who was dealing with dozens of people from the same JFK-Madrid flight) did not charge us extra to reschedule to a flight 8 hours later. They also gave us a voucher for breakfast and lunch. Glad the actual person at the airport had some actual sense.

As always, most AA flights that we fly are almost ALWAYS delayed and that too multiple times. Very frustrating

Boarding was smooth and seamless and the flight was without incident.

For an long range economy flight I feel more space and more meal options need to be offered for flights over 5 hours

Our flight was repeatedly delayed for maintenance problems: scheduled for 9.30am, eventually delayed to 7pm! Very very inconvenient! AA should have provided a substitute plane much earlier.. On the other hand, Customer Service crew in Charlotte helped us to reach NY (LGA) by late afternoon. Thank you Patricia!! The actual flight was quick and very comfortable. As always a. excellent, professional crew. [no food on a a short hop).

Take-off delayed an hour because of a missing flight officer, so,arrived in Charlotte lates causing many passengers to miss connections. Otherwise a very good flight, safe and comfortable, with an excellent professional crew.

Little time between flight from Dallas to flight to Gainesville. We chose this one, 43 minutes between, because the price for a connection with at least an hour between, was so much higher. Had to ask passengers on the Dallas flight to please allow us to deplane ahead of them. The economy passengers allowed this. We had to walk very fast to the next gate, 35 gates away. Thankfully all in the same terminal. Getting to the small Gainesville plane was a little confusing as you enter an area that is boarding many small planes at the same time. We stood in the wrong line for about 15 seconds before realizing it was not our Gainesville flight. Since I had boarded at this gate in the past, I knew to check the signs carefully so we weren’t lost. The first class seat experience was wonderful. I really enjoyed the upgrade. We were offered an alcohol drink as soon as we sat down. I got something different but it was a great gesture especially since we really had to hurry to make the flight. We had packed expecting we might miss this connection, but made it. Our luggage didn’t miss the flight. American Airlines delivered our bags to our home the next day. That was very convenient!

The plane was large, not full, but one with 3 seats near each window and 4 in a row in the middle of the plane. There were screens on the backs of the seats for entertainment and information. To use the entertainment one needs ear plugs that physically plug into the screen. My husband had some he let me use as I only had blue tooth type. The stewards gave out some headphones to some, but when my neighbor asked for some, the steward said no. So maybe they ran out? Idk. Bring the old kind of headphones or earbuds if you want entertainment in case this is the type of entertainment offered. We had a very tight connection in Miami. 43 minutes. The other economy passengers allowed us to get ahead of them because I asked if we could since we were near boarding time for our next flight and 35 gates away. They were extremely kind. First class wasn’t going to allow us to pass through. We did make the next flight. Our baggage didn’t, but they were delivered to us the next day and we were prepared with essentials in our carry on packs.

Food is what you expect on a plane. Nothing gluten free. But that is expected. Drinks, apple juice, was fine. Seat, what I expected. Fine.

The check in agents in PHL and gate agents had to have been the rudest women that I have ever encountered; the agent weighing the bags at check in screamed continuously at all of the guests as did the woman at the gate.I have Executive Platinum status with AA and fly a lot with AA but these ladies were the absolute worst I had the displeasure to encounter!

There weren't enough employees at check in took awhile to get bags checked. There wasn't a wheel chair for me, I was sent to someone who turns out to work for a different airline, if My flight hadn't been delayed I probably would have missed my flight as it was, by the time I arrived at my gate, they started boarding in about 15 minutes. I don't know who took me to my gate, definitely was not the normal people who take passengers to the gate. I'm guessing she may have been in a management position. I wish I knew her name, she went beyond to help me. With that said everyone was kind, and were doing the best they could. So, I choose to say it was an Adventure, stressful start, but good. In the end went well. The situation was not only difficult for passengers but the employee's.

The staff at the check in counter was so rude. Made you feel Incompetent

Frontier scheduled a 40 minute connection in DEN. What they failed to mention was that they “close the doors” 20 mins prior to departure, which means you only have 20 mins. Not enough time. Possibly against DOT regulations. Filing complaint.

Flight was scheduled at 9:40pm. Got delayed to 10 am, the next day. crazy

The bag check, flight check-in, and onboard experience convinced my wife and me that we will actively go out of our way to avoid flying Frontier Airlines in the future. At bag check, we were informed that check-in could only be completed via the Frontier mobile app. Unfortunately, the app was extremely frustrating—sending us through repetitive, confusing loops that repeatedly forced us to decline add-on services with nearly every click. While most airline apps upsell, this one felt intentionally exhausting. As the process dragged on, we became genuinely concerned that my phone battery would die before check-in could be completed. We approached the bag check staff—who were standing together talking—and explained both our frustration and our predicament. They laughed. Later, my wife described the interaction as “gaslighting,” which felt accurate. We were then informed it would cost $25 per person simply to have our boarding passes printed. From that point forward, the tone of the experience was consistently hostile. The bag check employees were condescending and combative, behaving more like bullies than customer service staff. Unfortunately, that same attitude continued onboard. One flight attendant argued with me when I attempted to stow my backpack in the overhead bin. I explained that we had each paid $75 to check our bags specifically so we would not need to use carry-on space and could have adequate legroom. She demanded to see my ticket, pointed out that it said “no carry-on”—which I acknowledged—and I reiterated that this was precisely why we paid to check our bags. Her response was, “I don’t make the rules.” She then walked away, but not before asking if I “truly wanted to fly back to Chicago today?”—an unnecessary and unmistakable threat. It is also worth noting that despite booking our tickets together in the same transaction, we were not seated together. Upon our return to Chicago—where we could once again sit together—we compared onboard experiences. We both remarked on how unhappy the flight attendants appeared and how each of us was separately asked whether we would like to purchase a beverage. We declined. At no point was water mentioned as an option, leaving us with the clear impression that even water came at a cost—or that complimentary water, if available at all, was deliberately left unmentioned. Overall, the experience was shocking and deeply disappointing, but it was also a profound learning experience—one we will not forget and will not repeat. -Steve

Plane was hot and miserable and the crew was rude!

12 hour delay required getting on and off plane 3 times - would have at least liked to have been offered a snack or drink

They didn’t offer a water, even after I asked

They switched our terminal 3 times and we were delayed for four plus hours!!!

It was an early flight and most people napped/slept and the crew let us which was nice.

Everything you need to know for your flight to Caribbean Islands

Information on your arrival and departure airports