$136 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 3/2. 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 Cana1 stop$483
Montego Bay
Montego Bay2 stops$480
Oranjestad
Oranjestad2 stops$538
Nassau
Nassau2 stops$534
Kingston
Kingston2 stops$455
Providenciales
Providenciales2 stops$580
Bridgetown
Bridgetown2 stops$934
George Town
George Town2 stops$516
Aguadilla
Aguadilla3 stops$531
Punta Cana
Punta Cana1 stop$483
Montego Bay
Montego Bay2 stops$480
Oranjestad
Oranjestad2 stops$538
Nassau
Nassau2 stops$534
Kingston
Kingston2 stops$455
Providenciales
Providenciales2 stops$580
Bridgetown
Bridgetown2 stops$934
George Town
George Town2 stops$516
Aguadilla
Aguadilla3 stops$531

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

Wed, Feb 25 - Wed, Mar 4
American Airlines Logo
6:00 am - 11:31 pm
COS
-
SJU
14h 31m
1 stop
American Airlines Logo
8:00 am - 10:10 pm
SJU
-
COS
17h 10m
2 stops
$272American Airlines
Wed, Feb 25 - Wed, Mar 4
American Airlines Logo
1:39 pm - 10:00 am
COS
-
SJU
17h 21m
2 stops
American Airlines Logo
7:00 am - 3:58 pm
SJU
-
COS
11h 58m
2 stops
$340American Airlines
Sun, Feb 15 - Wed, Feb 18
Delta Logo
1:22 pm - 11:58 pm
COS
-
SJU
7h 36m
1 stop
Delta Logo
6:15 am - 12:25 pm
SJU
-
COS
9h 10m
1 stop
$384Delta
Tue, Mar 31 - Sat, Apr 4
Delta Logo
6:20 am - 8:18 pm
COS
-
SJU
11h 58m
1 stop
Delta Logo
1:00 pm - 8:28 pm
SJU
-
COS
9h 28m
1 stop
$404Delta
Sun, Feb 15 - Wed, Feb 18
American Airlines Logo
4:49 pm - 10:00 am
COS
-
SJU
14h 11m
2 stops
American Airlines Logo
10:50 am - 10:10 pm
SJU
-
COS
14h 20m
2 stops
$408American Airlines
Tue, May 26 - Tue, Jun 2
United Airlines Logo
6:00 am - 5:38 pm
COS
-
SJU
9h 38m
1 stop
United Airlines Logo
1:00 am - 10:55 am
SJU
-
COS
11h 55m
2 stops
$412United Airlines
Tue, Mar 31 - Sat, Apr 4
American Airlines Logo
6:00 am - 10:58 pm
COS
-
SJU
14h 58m
2 stops
American Airlines Logo
9:50 am - 11:59 pm
SJU
-
COS
16h 09m
2 stops
$424American Airlines
Tue, Mar 31 - Sat, Apr 4
Delta Logo
6:20 am - 8:18 pm
COS
-
SJU
11h 58m
1 stop
Delta Logo
1:00 pm - 8:28 pm
SJU
-
COS
9h 28m
1 stop
$433Delta
Mon, Feb 23 - Fri, Feb 27
United Airlines Logo
5:59 am - 6:18 pm
COS
-
PUJ
9h 19m
1 stop
United Airlines Logo
2:55 pm - 10:55 am
PUJ
-
COS
23h 00m
1 stop
$518United Airlines
Sun, Jun 7 - Sat, Jun 13
Southwest Logo
8:55 pm - 1:15 pm
COS
-
NAS
14h 20m
2 stops
Southwest Logo
8:45 am - 4:15 pm
NAS
-
COS
9h 30m
2 stops
$788Southwest
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 $373, 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 November, when tickets cost $463 (return) on average. On the other hand, the most expensive months are August and March, when the average cost of round-trip tickets is $641 and $637 respectively.

How far in advance should I book a flight from Colorado Springs 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 Colorado Springs 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 Colorado Springs to Caribbean Islands, you should book around 3 weeks before departure, which saves you about 12% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 13 weeks before departure.

Good to know

Low seasonSeptember
Cheapest flight$136
Best time to beat the crowds with an average 25% drop in price.
Most popular time to fly and prices are also 6% lower on average.
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 airline 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.
7.2
American AirlinesOverall score based on 11211 reviews
7.2Comfort
8.0Crew
7.5Boarding
6.4Food
6.9Entertainment
Airline reviews

Update to handle the delay was very bad, crews no smiles or welcome or thanks. Don’t care attitude

2.0 MediocreManikandan, Jan 2026
DFW - ORD
Read more American Airlines reviews

Update to handle the delay was very bad, crews no smiles or welcome or thanks. Don’t care attitude

It would be nice to have some low carb options in the snacks.

I was trying to take 2 one and a half hour one way trips and I experienced almost 20 delays over the course of those two trips. Only a few of them were due to weather the rest was disorganization

No gates avail at DFW so our incoming had to wait 30 mins for a plane to push back because they Had mechanical. We boarded 90 mins delayed and then we had a mechanical. Come on American…do better. Also at my seat the tray table had not been cleaned. Floor had not been cleaned. But captain and flight Att were very picture and apologetic.

Crew was helpful and cheerful especially when they had no refreshments to work with. The plane was never serviced and had nothing but limited water and coffee onboard. For the price point, a concern of services.

Flight was smooth, quick and felt safe. The 2 delays not happening would have been better but I guess that happens in the airline industry

Flight was canceled. I asked to be rerouted to OKC and then took an Uber.

AA did not allow to board a flight because my connecting flight from DFW had been canceled. I got on another flight to another city. No service on the plane and I did not use their entertainment system.

On time on a day with lots of weather cancellations on other flights. Thank you for getting me home during a winter storm!

Don't change gate multiple times make people run across the airport. Announce delays in a timely manner. Have maintenance crew ready. Don't delay and keep passengers on the plane for 3 hrs. on tarmac.

Everything you need to know for your flight to Caribbean Islands

Information on your arrival and departure airports