$133 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 1/18. 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$466
Santo Domingo
Santo Domingo2 stops$518
Montego Bay
Montego Bay2 stops$541
Oranjestad
Oranjestad1 stop$512
Nassau
Nassau1 stop$559
Kingston
Kingston2 stops$696
Providenciales
Providenciales2 stops$769
Bridgetown
Bridgetown2 stops$686
George Town
George Town1 stop$600
Punta Cana
Punta Cana2 stops$466
Santo Domingo
Santo Domingo2 stops$518
Montego Bay
Montego Bay2 stops$541
Oranjestad
Oranjestad1 stop$512
Nassau
Nassau1 stop$559
Kingston
Kingston2 stops$696
Providenciales
Providenciales2 stops$769
Bridgetown
Bridgetown2 stops$686
George Town
George Town1 stop$600

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

Tue, Mar 10 - Wed, Mar 11
American Airlines Logo
10:53 am - 8:36 amCOS-SJU
19h 43m2 stops
American Airlines Logo
3:45 pm - 11:30 amSJU-COS
21h 45m2 stops
$337American Airlines
Find Deal
Fri, Jan 9 - Sun, Jan 18
Multiple Airlines Logo
10:30 am - 1:05 pmCOS-SJU
23h 35m1 stop
Multiple Airlines Logo
7:00 am - 9:40 amSJU-COS
29h 40m1 stop
$391Multiple Airlines
Find Deal
Fri, Jan 9 - Sun, Jan 18
Multiple Airlines Logo
10:30 am - 1:05 pmCOS-SJU
23h 35m1 stop
Multiple Airlines Logo
7:10 am - 9:40 amSJU-COS
29h 30m2 stops
$410Multiple Airlines
Find Deal
Fri, Jan 9 - Sun, Jan 18
American Airlines Logo
1:06 pm - 10:48 amCOS-SJU
18h 42m2 stops
American Airlines Logo
6:00 am - 5:41 pmSJU-COS
14h 41m2 stops
$435American Airlines
Find Deal
Mon, Mar 16 - Mon, Mar 30
United Airlines Logo
6:53 pm - 11:49 amCOS-SJU
14h 56m2 stops
United Airlines Logo
1:05 am - 11:18 amSJU-COS
12h 13m2 stops
$474United Airlines
Find Deal
Wed, Feb 18 - Tue, Feb 24
United Airlines Logo
6:55 pm - 1:49 pmCOS-PUJ
15h 54m2 stops
United Airlines Logo
2:05 pm - 10:02 pmPUJ-COS
10h 57m1 stop
$500United Airlines
Find Deal
Wed, Mar 18 - Mon, Mar 30
Southwest Logo
7:25 am - 7:30 pmCOS-SJU
10h 05m2 stops
Southwest Logo
8:50 pm - 10:05 amSJU-COS
15h 15m2 stops
$503Southwest
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Sat, Apr 4 - Mon, Apr 6
Southwest Logo
6:50 am - 5:35 pmCOS-SJU
8h 45m2 stops
Southwest Logo
10:15 am - 9:50 pmSJU-COS
13h 35m2 stops
$525Southwest
Find Deal
Tue, Dec 30 - Tue, Jan 6
Delta Logo
2:00 pm - 9:44 pmCOS-NAS
5h 44m1 stop
Delta Logo
4:28 pm - 12:24 pmNAS-COS
21h 56m2 stops
$559Delta
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Mon, Mar 16 - Thu, Apr 2
Delta Logo
6:00 am - 7:29 pmCOS-SJU
11h 29m1 stop
Delta Logo
6:15 am - 1:05 pmSJU-COS
8h 50m1 stop
$571Delta
Find Deal
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 $339, 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 October, when tickets cost $469 (return) on average. On the other hand, the most expensive months are March and December, when the average cost of round-trip tickets is $735 and $658 respectively.

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

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

If your flying dates are flexible, you should consider flying to Caribbean Islands on a Monday, as we generally find the cheapest rates on that day for this route. On the other hand, Friday is the most expensive day to fly from Colorado Springs to Caribbean Islands. For your return ticket, we recommend flying on a Friday and avoiding Sundays for the best deals.

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 1 week before departure. For the absolute cheapest price, our data suggests you should book 12 weeks before departure.

Good to know

Low seasonSeptember
Cheapest flight$133
Best time to beat the crowds with an average 28% drop in price.
Most popular time to fly and prices are also 9% 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.

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

    The cheapest time of day to fly to Caribbean Islands is generally in the evening, when round-trip flights cost $557 on average. Morning departures are around 3% more expensive than evening flights, 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 $576.

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 11030 reviews
7.2Comfort
7.5Boarding
6.4Food
6.9Entertainment
8.0Crew
Airline reviews

The flight attendant, a black woman with curly hair who sat near Row 21, was wonderful and kind.

10.0 ExcellentMax, Oct 2025DCA - SAV
Read more American Airlines reviews

The flight attendant, a black woman with curly hair who sat near Row 21, was wonderful and kind.

It was good..clean, comfy seat. Friendly warm welcoming crew. Was able to check my cabin luggage at the gate which I was able to pickup in a decent time from baggage claim. The app gave all updates from delays to baggage claim info. Overall smooth flight.

Flight was delayed leaving Dallas. Arrived about 2 hours later than scheduled.

Flight delayed and missed connection. Rescheduled flight cancelled after 6 hrs wait. Rerouted thru ORD, flight cancelled, overnight stay in ORD. Still in the air on new flight!

We are too tired and frustrated to comment politely at this point

Terrible. Our luggage was delayed and couldn’t be delivered for several days. We got bad information from the airline agents at baggage claim. We had to pick up our car so we wouldn’t be charged for an extra day. We got lost in the maze of airport parking. The baggage claim agents didn’t offer us any compensation for our extra time and expense. We are tired, hungry and very frustrated.

The flight was flawless and we even arrived between 20 and 25 minutes early!

The only thing to like was that we eventually got to our destination

Delayed delayed delayed and no offer for food or vouchers

Disliked having to wait a little longer to disembark from the plan when we landed in London

Everything you need to know for your flight to Caribbean Islands

Information on your arrival and departure airports

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