$214 Find Cheap Flights from Colorado Springs to Caribbean

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 departing on 4/17. 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

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Cheap Flights from Colorado Springs to Caribbean

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Punta Cana
Punta Cana2 stops$553
Montego Bay
Montego Bay2 stops$397
Oranjestad
Oranjestad1 stop$612
Nassau
Nassau1 stop$641
Kingston
Kingston2 stops$972
Providenciales
Providenciales2 stops$858
Bridgetown
Bridgetown2 stops$1,818
George Town
George Town2 stops$596
Aguadilla
Aguadilla2 stops$783
Punta Cana
Punta Cana2 stops$553
Montego Bay
Montego Bay2 stops$397
Oranjestad
Oranjestad1 stop$612
Nassau
Nassau1 stop$641
Kingston
Kingston2 stops$972
Providenciales
Providenciales2 stops$858
Bridgetown
Bridgetown2 stops$1,818
George Town
George Town2 stops$596
Aguadilla
Aguadilla2 stops$783

Book Cheap Colorado Springs to Caribbean 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 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

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
1:31 pm - 11:32 pm
SJU
-
COS
12h 01m
2 stops
$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
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
Mon, Aug 17 - Sat, Aug 22
Delta Logo
5:55 pm - 2:51 pm
COS
-
PUJ
18h 56m
2 stops
Delta Logo
1:05 pm - 9:15 pm
PUJ
-
COS
10h 10m
1 stop
$557Delta
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 flights

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

Which airlines provide the cheapest flights from Colorado Springs to Caribbean?

The cheapest round-trip price for the route for each airline clicked by KAYAK users in the last 72 hours.

In the past 3 days, the cheapest round-trip tickets from Colorado Springs to Caribbean were found on American Airlines ($373) and Southwest ($396).

Good to know

Low seasonSeptember
Cheapest flight$214
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 San Juan

FAQs - booking Caribbean flights

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

    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.

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

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

    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 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?

    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 up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Reviews of the top 4 airlines serving from Colorado Springs to Caribbean

 
Need help choosing which airline to fly with from Colorado Springs to Caribbean? 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.
8.0
SouthwestOverall score based on 4318 reviews
8.1Boarding
8.6Crew
7.0Food
8.0Comfort
7.5Entertainment
Airline reviews

Long layover between flights to Long Island from BWI - need better coordination between flights

4.0 OkayKenny, Mar 2026
TPA - BWI
Read more Southwest reviews

Long layover between flights to Long Island from BWI - need better coordination between flights

I elected to pay for the upgrades and found very little difference

The new seating arrangement is so over priced for what you get.

The problem with the seat assignments is that there were a lot of rows in the front that were empty but my row at the back was full. Just not so pleasant.

No food or entertainment, just a quick 40 minute flight. A little bumpy due to Santa Ana winds but pilot has no control over that. Good flight and landing!

Good but I prefer choose your own seat. With the new assigned seats they should board from the back I see no advantage to this new boarding. Just like every other airline

I realize they are still working out kinks with the new boarding process, but by the time I boarded in group 5, most of the bins were full. All airlines should better enforce small bags and jackets going under the seats until everyone has boarded.

WiFi was not working and didn’t have a beverage service

Snacks are always pretzels. Why can't you also offer peanuts ?

Flight boarded late after announcing on time boarding. Flight arrived only a little late despite late departure. Had trouble connecting to WiFi

First class is comfortable. Enjoyed a movie and was able to relax compared to coach.

Loved flying First Class. Very comfortable. The seat was amazing. Enjoyed a movie and was able to relax so much better than in coach.

We landed and sat on the tarmac for 45 minutes because they only have one gate at the airport and there was another plane running late so we had to wait

The WiFi was not working. That made for a long flight.

With Aeromexico it ended up good but with Delta it was bad because we did everything through Delta... Showed up at the Delta terminal... It was the wrong place! Nothing ever told us to go to the Aeromexico terminal. It said "in partnership with Aeromexico" but I was never instructed to check in with them or go to their terminal. We had to haul @$$ running through the airport and almost didn't make it thanks to this poor communication. 👎🏽

Absolutely no communication on why there's a delay and multiple flight time reschedules. I would have canceled the flight and drove back home if I known it was going to be rescheduled 3 or 4 times.

Another late night flight and MORE men belligerently drinking and yelling. I had to move from first to economy because they were so obnoxious and disruptive. Crazy to go from a cozy chair to cardboard when you were supposed to be in first. Delta allows was too much drinking which leads to belligerent behavior.

I was in first class and literally the men behind me were so aggressively loud I moved myself to economy. This has become so common on Delta - people using audio without headphones, and men on 12am / late night flights drinking and yelling to talk to each other which prevents anyone around them from resting. Pretty crazy to have to move from first to economy (poorer service, less comfort...). Wild wild. Looking into other airlines.

Love delta smaller commuter plane so no entertainment and paid wifi on MKE-LGA leg was extremely unreliable and slow

Stop changing gates. Stop cancelling flights Stop moving my seat.

Flight left on time and we arrived 25 minutes early! There was a gate available when we arrived so early on a busy Sunday afternoon! Flight attendants came around twice with the drinks cart.

Both of my flights arrived early and check in process was smooth

Sitting on the runway after we land for almost two hours! Not sure if we should blame United or Just Dumpy Vance.

Flight was late - I was downgraded from first class to coach

United overall experience is great these days. Airport experience was very organized. Staff on flight were great. App and information as good as it gets.

Great smooth flight. Had a seating change, but that was an improvement. Thanks United Airways Crew.

Flight was good but there are way to many announcements for credit cards etc.

Crew seemed a bit cranky. No seatback screens. But boarding was efficient and on time and we arrived early.

See previous note about the passenger in Denver who threw my husband's bag out of the overhead bin in order to maker room for his own. And the flight attendant back up the new passenger.

Terrible. They wouldn't allow me on my flight on the 14th..

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

Information on your arrival and departure airports