$228 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 6/22. 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
Travelers love KAYAK
41,299,237 searches in the past 7 days on KAYAK

Save 23% 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 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$553
Santo Domingo
Santo Domingo2 stops$938
Montego Bay
Montego Bay2 stops$397
Oranjestad
Oranjestad1 stop$612
Nassau
Nassau2 stops$655
Saint Thomas Island
Saint Thomas Island2 stops$563
Kingston
Kingston2 stops$956
Providenciales
Providenciales2 stops$800
Bridgetown
Bridgetown2 stops$1,813
George Town
George Town2 stops$560
Aguadilla
Aguadilla2 stops$783
Punta Cana
Punta Cana2 stops$553
Santo Domingo
Santo Domingo2 stops$938
Montego Bay
Montego Bay2 stops$397
Oranjestad
Oranjestad1 stop$612
Nassau
Nassau2 stops$655
Saint Thomas Island
Saint Thomas Island2 stops$563
Kingston
Kingston2 stops$956
Providenciales
Providenciales2 stops$800
Bridgetown
Bridgetown2 stops$1,813
George Town
George Town2 stops$560
Aguadilla
Aguadilla2 stops$783

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

Sat, May 2 - Sat, May 9
American Airlines Logo
1:39 pm - 10:53 am
COS
-
SJU
19h 14m
2 stops
American Airlines Logo
10:01 am - 11:32 pm
SJU
-
COS
15h 31m
2 stops
$322American Airlines
Tue, Apr 14 - Wed, Apr 22
American Airlines Logo
5:41 am - 6:10 pm
COS
-
SJU
10h 29m
2 stops
American Airlines Logo
6:45 am - 11:32 pm
SJU
-
COS
18h 47m
1 stop
$333American Airlines
Sat, May 2 - Sat, May 9
American Airlines Logo
1:39 pm - 11:02 pm
COS
-
SJU
7h 23m
1 stop
American Airlines Logo
11:59 pm - 4:23 pm
SJU
-
COS
18h 24m
1 stop
$364American Airlines
Sat, May 2 - Sat, May 9
American Airlines Logo
1:39 pm - 9:13 am
COS
-
SJU
17h 34m
2 stops
American Airlines Logo
11:59 pm - 12:49 pm
SJU
-
COS
14h 50m
1 stop
$373American Airlines
Sat, May 2 - Thu, May 7
Southwest Logo
6:20 am - 3:35 pm
COS
-
SJU
7h 15m
1 stop
Southwest Logo
6:50 am - 3:30 pm
SJU
-
COS
10h 40m
2 stops
$396Southwest
Tue, Apr 28 - Tue, May 5
United Airlines Logo
5:13 pm - 3:10 pm
COS
-
MBJ
20h 57m
2 stops
United Airlines Logo
2:40 pm - 9:31 pm
MBJ
-
COS
7h 51m
1 stop
$413United Airlines
Sat, May 2 - Sat, May 9
Delta Logo
6:15 am - 8:24 pm
COS
-
SJU
12h 09m
1 stop
Delta Logo
2:48 pm - 9:27 pm
SJU
-
COS
8h 39m
1 stop
$416Delta
Tue, Mar 31 - Sat, Apr 4
Delta Logo
6:20 am - 4:18 pm
COS
-
SJU
7h 58m
1 stop
Delta Logo
12:00 pm - 10:05 pm
SJU
-
COS
12h 05m
2 stops
$454Delta
Mon, May 4 - Mon, May 11
United Airlines Logo
5:12 pm - 1:30 pm
COS
-
MBJ
19h 18m
2 stops
United Airlines Logo
2:40 pm - 9:31 pm
MBJ
-
COS
7h 51m
1 stop
$465United Airlines
Wed, Jun 24 - Sun, Jun 28
Southwest Logo
5:35 am - 6:30 pm
COS
-
NAS
10h 55m
2 stops
Southwest Logo
2:10 pm - 12:45 am
NAS
-
COS
12h 35m
2 stops
$656Southwest
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 $360, prices are generally cheapest when you fly direct.

Find deals

Good to know

Low seasonSeptember
Cheapest flight$228
Best time to beat the crowds with an average 27% drop in price.
Most popular time to fly with an average 9% increase in price.
Flight from Colorado Springs to Nassau

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.
7.1
American AirlinesOverall score based on 11467 reviews
6.9Entertainment
7.5Boarding
6.4Food
7.9Crew
7.2Comfort
Airline reviews

After changing the departure gate 5 times making us mo e from one side of the airport to the other and then back the flight was delayed nearly 2 hours. The male flight attendant had a bad attitude with the guest being condescending, disrespectful with people who were already on edge.

2.0 Mediocresteven, Mar 2026
MIA - CLE
Read more American Airlines reviews

After changing the departure gate 5 times making us mo e from one side of the airport to the other and then back the flight was delayed nearly 2 hours. The male flight attendant had a bad attitude with the guest being condescending, disrespectful with people who were already on edge.

Easy boarding. Rows are smaller but that may be an older and bigger me now :)

It would have been nice if American tried to care.

American Airlines did everything they could with the high Spring Break crowd. I was frustrated to be changed from 1st class to a middle seat at the back of the plane. This has happened before, not sure booking 1st class and paying the extra actually works.

I booked 1st class, my flights were changed and I was sitting in the middle at the back of the plane. A far cry from the 1st class I purchased for my flights. I am grateful I arrived on time.

Aging planer and NO wifi on a 14 hour day flight. Unless you are retired or don't need to work or be in touch with the world... The lack of Wifif really ruined the flight. And the old plane - really showing it's age, wasn't great

There was no beverage service and the only time I saw a crew member walk through the cabin is when we were preparing to land.

Our flight was delayed 3 times and this is why I am giving such low reviews. Everything else was okay but being in the airport at 4:30pm for my initial flight at 7pm to not leave until after 9:30pm is insane,

Flights were constantly delayed. CRW took 50 minutes to get bags

Flight has been delayed every time I've ever taken it. Seats uncomfortable. Children behind me yelling the entire flight. Some of this is out of their control but overall just consistently not a great experience.

Everything you need to know for your flight to Caribbean Islands

Information on your arrival and departure airports

Colorado Springs (COS)