$152 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 3/23. 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 Cana1 stop$513
Santo Domingo
Santo Domingo2 stops$621
Montego Bay
Montego Bay1 stop$352
Oranjestad
Oranjestad2 stops$572
Nassau
Nassau2 stops$570
Kingston
Kingston2 stops$485
Bridgetown
Bridgetown2 stops$1,132
George Town
George Town2 stops$482
Punta Cana
Punta Cana1 stop$513
Santo Domingo
Santo Domingo2 stops$621
Montego Bay
Montego Bay1 stop$352
Oranjestad
Oranjestad2 stops$572
Nassau
Nassau2 stops$570
Kingston
Kingston2 stops$485
Bridgetown
Bridgetown2 stops$1,132
George Town
George Town2 stops$482

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, Apr 18 - Fri, Apr 24
American Airlines Logo
5:13 pm - 4:32 am
COS
-
SJU
9h 19m
1 stop
American Airlines Logo
7:00 pm - 9:27 am
SJU
-
COS
16h 27m
2 stops
$348American Airlines
Tue, Mar 24 - Tue, Mar 31
American Airlines Logo
6:00 am - 2:04 pm
COS
-
MBJ
7h 04m
1 stop
American Airlines Logo
3:04 pm - 10:10 pm
MBJ
-
COS
8h 06m
1 stop
$352American Airlines
Tue, Mar 24 - Tue, Mar 31
American Airlines Logo
5:07 pm - 1:26 pm
COS
-
MBJ
19h 19m
2 stops
American Airlines Logo
1:27 pm - 12:48 pm
MBJ
-
COS
24h 21m
2 stops
$357American Airlines
Sat, Apr 18 - Fri, Apr 24
American Airlines Logo
5:13 pm - 4:32 am
COS
-
SJU
9h 19m
1 stop
American Airlines Logo
11:59 pm - 4:23 pm
SJU
-
COS
18h 24m
1 stop
$360American Airlines
Mon, May 11 - Thu, May 14
Southwest Logo
10:35 am - 11:55 pm
COS
-
SJU
11h 20m
2 stops
Southwest Logo
10:00 am - 10:15 pm
SJU
-
COS
14h 15m
2 stops
$376Southwest
Mon, May 11 - Fri, May 15
United Airlines Logo
5:12 pm - 12:30 pm
COS
-
GCM
18h 18m
2 stops
United Airlines Logo
1:35 pm - 8:47 am
GCM
-
COS
20h 12m
2 stops
$482United Airlines
Fri, Apr 10 - Fri, Apr 17
United Airlines Logo
1:33 pm - 12:27 pm
COS
-
SXM
20h 54m
2 stops
United Airlines Logo
1:35 pm - 11:05 am
SXM
-
COS
23h 30m
2 stops
$508United Airlines
Mon, Mar 23 - Mon, Mar 30
Delta Logo
8:15 am - 11:47 am
COS
-
GCM
26h 32m
2 stops
Delta Logo
1:12 pm - 8:28 pm
GCM
-
COS
8h 16m
1 stop
$528Delta
Mon, Mar 23 - Thu, Mar 26
Delta Logo
12:10 pm - 1:54 pm
COS
-
SXM
23h 44m
2 stops
Delta Logo
12:55 pm - 8:28 pm
SXM
-
COS
9h 33m
1 stop
$540Delta
Thu, Apr 9 - Thu, Apr 16
Southwest Logo
7:20 pm - 1:15 pm
COS
-
NAS
15h 55m
2 stops
Southwest Logo
8:45 am - 9:45 pm
NAS
-
COS
15h 00m
2 stops
$570Southwest
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 ($348) and Delta ($438).

Good to know

Low seasonSeptember
Cheapest flight$152
Best time to beat the crowds with an average 27% drop in price.
Most popular time to fly with an average 6% increase in price.
Flight from Colorado Springs to Montego Bay

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 4301 reviews
7.0Food
8.1Boarding
8.0Comfort
7.5Entertainment
8.6Crew
Airline reviews

It was canceled. Supposedly weather. But there was no snow in Baltimore. At least we found out before driving to airport

2.0 MediocreAnonymous, Feb 2026
BWI - PBI
Read more Southwest reviews

It was canceled. Supposedly weather. But there was no snow in Baltimore. At least we found out before driving to airport

I have not flown Southwest in awhile and had a very pleasant experience. From ticketing to boarding to the flight. The flight left on time and landed ahead of schedule. It won't be so long next time!!

The Southwest experience has definitely taken a dive from its early days. You can no longer deferentiate from other airlines. Air travel is too expensive. Southwest is no longer budget friendly. They have lost me as a loyal customer.

Flight was hours late, unable to sit next to spouse, I have had so much better experiences. Substantially better, only saving grace was that it was a short flight.

An entire day of delays. Cost lots of money. Meals and a hotel.

The WiFi and crew on the plane were good, however, the boarding experience was awful. I paid for the Choice Preferred and was boarded in group 5 so all overhead storage was full. They found room for our luggage, but further back making getting off the plane a nightmare. Also, we were in row 6 and the seats were extremely uncomfortable. Both my daughter and I had no leg room and couldn’t wait to get off the plane.

The charges were ridiculous for an hour flight and the turbulence was very scary.

Still need to work out the kinks on the new assigned seating boarding process. Otherwise, a very good flight.

WiFi did not work. Boarding with the new seating assignments took too long. The temperature in the terminal was obnoxious. +/- 80°

The seats are now more narrow. I paid for front row the seats in the front are even more narrow than before.

Everything was good except wifi and a leaking drink chiller. The floor was all wet and my bag was soaked. Did not notice until debarking. Have not heard back from Delta. Even though this was leg one of an international flight in first class, they denied access to their Sky Club - very disappointing!

The staff was fine. The plane was extremely tight, and I paid for the wifi and it did not work at all. I was actually going to ask for a refund.

two hour delay and the Delta representative on the PA system was unable to understand

An awesome flight crew. FC seat cushion just doesn’t cut it for a 3+ hour flight.

2+hrs delay without any reason provided and a cramped flight

We waited an hour on the runway to get a gate in Orlando

Flight was delayed by 3-hours and their fix was… complimentary pretzels.

Flight was delayed due to crew being not on time

Flight crew issues delayed my flight by 2 1/2 hours. Causing me to miss my connection.

The staff on board and gate was nice - a welcome change from the usual. We also arrived early, which was a great benefit, given that it takes 30 minutes plus to get bags at SRQ.

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..

Lack of gluten free options in food service. I have Celiac disease and it appears you no longer offer special meals for people with dietary restrictions. I am a frequent flyer traveling into and out of Omaha airport. I have noticed over the course of several months that although our flight typically arrives ahead of schedule (awesome job AA!) - we typically sit on the runway for several minutes waiting for the ground crew to get in place. Not sure if it is a ground crew issue or a gate availability issue (due to construction at this airport). Seems to be more of a ground crew being on time issue.

Arrived early picked up my bag in a few minutes- great trip - thank you

Flight boarded, departed and landed on time. Excellent service from flight attendant in FIRST

Boarding is always an ordeal. Less dogs on flights. I am highly allergic to dogs and cats. Why are there so many animals these days?

Flight to Tampa was delayed taking off due to plane arriving late but no other issues

There was a delay with the plan which cause the flight to leave later and once arrived in Chicago there was another delay and some passengers missed their connecting flights

Massimo, flight attendant was very authentic, attentive - wonderful. Food/wrap was just okay.

Worst experience ever. Flight could not land in Charlotte for what we were told was a ground stop. Had to be diverted to Raleigh to refuel. Strangely during ground stop, our connecting flight had no issue taking off on time causing us to miss our flight. We were told there were no other flights that day to our final destination and that two days out was the next one. The only flights to get us there were from Chicago the next morning. Completely opposite direction but it was a direct flight. So we get flown to Chicago and have to find a hotel in our own dime. The flight in the morning was also delayed. Thankfully only a short time. The non too of all this, our luggage did not arrive by the time we were there. Communication was terrible, through the entire trip. Complete incompetence. Will never fly American again.

Horrible. Got delayed many hours because their pilot wasn't trained for night landing at the airport and a rain delay made it a night landing. We have to wait hours for a qualified crew. They give us 12 dollar meal vouchers but most everything in the airport was closed and definitely more expensive than the vouchers.

I am an AA flyer for a very long time... AA has yet to disappoint.

Everything you need to know for your flight to Caribbean

Information on your arrival and departure airports