$175 Find Cheap Flights from Colorado Springs 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 Colorado Springs to Caribbean Islands departing on 9/28. 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 Colorado Springs 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 Colorado Springs to Caribbean Islands, as well as popular online travel agencies
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Flight Deals

Cheap Flights from Colorado Springs to Caribbean Islands

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Punta Cana
Punta Cana2 stops$521
Santo Domingo
Santo Domingo2 stops$727
Montego Bay
Montego Bay1 stop$427
Oranjestad
Oranjestad2 stops$693
Nassau
Nassau1 stop$508
Kingston
Kingston2 stops$2,321
Providenciales
Providenciales2 stops$760
Bridgetown
Bridgetown2 stops$1,159
George Town
George Town2 stops$636
Aguadilla
Aguadilla2 stops$362
Punta Cana
Punta Cana2 stops$521
Santo Domingo
Santo Domingo2 stops$727
Montego Bay
Montego Bay1 stop$427
Oranjestad
Oranjestad2 stops$693
Nassau
Nassau1 stop$508
Kingston
Kingston2 stops$2,321
Providenciales
Providenciales2 stops$760
Bridgetown
Bridgetown2 stops$1,159
George Town
George Town2 stops$636
Aguadilla
Aguadilla2 stops$362

Book Cheap Colorado Springs 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 Colorado Springs 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 Colorado Springs to Caribbean Islands

jue., ago. 27 - mié., sep. 2
American Airlines Logo
3:51 pm - 9:43 am
COS
-
SJU
15h 52m
2 stops
American Airlines Logo
10:33 am - 10:53 pm
SJU
-
COS
14h 20m
2 stops
$352American Airlines
mié., ago. 26 - lun., ago. 31
American Airlines Logo
12:37 pm - 11:15 pm
COS
-
SJU
8h 38m
1 stop
American Airlines Logo
7:24 pm - 9:18 am
SJU
-
COS
15h 54m
2 stops
$357American Airlines
jue., ago. 27 - mié., sep. 2
American Airlines Logo
3:51 pm - 9:43 am
COS
-
SJU
15h 52m
2 stops
American Airlines Logo
3:44 pm - 10:53 pm
SJU
-
COS
9h 09m
1 stop
$362American Airlines
mié., oct. 14 - vie., oct. 23
Southwest Logo
10:30 am - 11:45 pm
COS
-
SJU
11h 15m
2 stops
Southwest Logo
5:30 am - 4:20 pm
SJU
-
COS
12h 50m
2 stops
$374Southwest
vie., sep. 25 - dom., sep. 27
Delta Logo
6:14 pm - 12:13 pm
COS
-
SJU
15h 59m
2 stops
Delta Logo
12:58 pm - 7:36 pm
SJU
-
COS
8h 38m
1 stop
$376Delta
mié., ago. 26 - lun., ago. 31
United Airlines Logo
7:40 am - 8:38 pm
COS
-
SJU
10h 58m
1 stop
United Airlines Logo
2:20 pm - 9:27 pm
SJU
-
COS
9h 07m
1 stop
$390United Airlines
vie., sep. 25 - dom., sep. 27
United Airlines Logo
7:40 am - 8:38 pm
COS
-
SJU
10h 58m
1 stop
United Airlines Logo
2:00 pm - 10:06 pm
SJU
-
COS
10h 06m
1 stop
$410United Airlines
lun., oct. 5 - lun., oct. 12
Southwest Logo
8:55 pm - 10:40 am
COS
-
SJU
11h 45m
2 stops
Southwest Logo
6:30 am - 4:20 pm
SJU
-
COS
11h 50m
2 stops
$413Southwest
vie., sep. 25 - dom., sep. 27
Delta Logo
6:14 pm - 12:13 pm
COS
-
SJU
15h 59m
2 stops
Delta Logo
12:58 pm - 7:36 pm
SJU
-
COS
8h 38m
1 stop
$415Delta
vie., oct. 16 - vie., oct. 23
British Airways Logo
1:09 pm - 4:10 pm
COS
-
GCM
26h 01m
3 stops
British Airways Logo
6:05 pm - 10:57 pm
GCM
-
COS
29h 52m
3 stops
$8,194British Airways
Booking Insights

KAYAK's insights & trends for Colorado Springs to Caribbean Islands flights

Get data-powered insights and trends into flights from Colorado Springs 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 Colorado Springs 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 $410, prices are generally cheapest when you fly direct.

What is the cheapest month to fly from Colorado Springs to Caribbean Islands?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Colorado Springs 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 Colorado Springs to Caribbean Islands is March, when tickets cost $0 (return) on average. On the other hand, the most expensive months are June and November, when the average cost of round-trip tickets is $820 and $621 respectively.

Good to know

Low seasonSeptember
Cheapest flight$175
Best time to beat the crowds with an average 27% drop in price.
Most popular time to fly with an average 14% increase in price.
Flight from Colorado Springs to San Juan

FAQs - booking Caribbean Islands flights

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

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Colorado Springs 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 Colorado Springs 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 Colorado Springs 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 Colorado Springs 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 Colorado Springs 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 airlines flying from Colorado Springs to Caribbean Islands

 
See real verified KAYAK customer reviews for airlines flying from Colorado Springs 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 Colorado Springs 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.
7.4
United AirlinesOverall score based on 9859 reviews
6.6Food
7.7Boarding
8.1Crew
7.3Comfort
7.1Entertainment
Airline reviews

The entertainment they offer could use some games, and maybe they could add some cookies to the snack menu. And the automated messages are a bit repetitive. But it was comfortable temperature wise and the seats were comfortable. The crew is very polite and helpful

6.0 GoodAnonymous, Jun 2026
DEN - YEG
Read more United Airlines reviews

The entertainment they offer could use some games, and maybe they could add some cookies to the snack menu. And the automated messages are a bit repetitive. But it was comfortable temperature wise and the seats were comfortable. The crew is very polite and helpful

This planes staff was top tier. Everything went great and had a great flight home.

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.

Excellent service. Flight attendance like Jessica,, on our flight, is a reason I wouldn’t mind flying through British Airways again. Jessica,, was very courteous and helpful.

The seats were extremely cramped, with very little legroom or personal space. There was no room left in the overhead bins for a backpack, and the space under the seat in front was so limited that I could barely fit my bag underneath. Overall, the seating arrangement felt very uncomfortable and overcrowded.

Significant delays on my trip to Chicago and my trip back to NY

Terrible boarding and first class experience. Nice staff but overall disorganized, dirty plane.

Delayed by 5 hours and I had to wit in the airport for more than 6+ hours.

weather delay of almost 2 hours then we landed and our gate wasn't available so we waited another 30 min

Flight had mechanical issues and it was delayed 30 mins - some of us boarded and then had to deplane.

technology worked well and everything ran smoothly. The seats are quite cramped so please don't try to re-engineer the cabin to squeeze more bodies on board.

Delayed flight more than I hour. When boarding we spent some additional time on the plane before takeoff ....

Flight was delayed due to connecting passengers. Lack of snack options bad. Sitting in Aisle, last cart run pulled the cart directly into my knee. Rude awakening.

Everything you need to know for your flight to Caribbean Islands

Information on your arrival and departure airports