$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 4/3. 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$513
Santo Domingo
Santo Domingo2 stops$429
Montego Bay
Montego Bay2 stops$357
Oranjestad
Oranjestad2 stops$580
Nassau
Nassau1 stop$630
Kingston
Kingston2 stops$505
Providenciales
Providenciales1 stop$703
Bridgetown
Bridgetown2 stops$914
George Town
George Town2 stops$551
Punta Cana
Punta Cana2 stops$513
Santo Domingo
Santo Domingo2 stops$429
Montego Bay
Montego Bay2 stops$357
Oranjestad
Oranjestad2 stops$580
Nassau
Nassau1 stop$630
Kingston
Kingston2 stops$505
Providenciales
Providenciales1 stop$703
Bridgetown
Bridgetown2 stops$914
George Town
George Town2 stops$551

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

Wed, Apr 22 - Tue, Apr 28
American Airlines Logo
1:39 pm - 9:13 am
COS
-
SJU
17h 34m
2 stops
American Airlines Logo
7:00 pm - 12:49 pm
SJU
-
COS
19h 49m
2 stops
$282American 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
5:45 am - 4:23 pm
SJU
-
COS
12h 38m
2 stops
$344American 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 - 12:49 pm
SJU
-
COS
14h 50m
1 stop
$351American 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
1:31 pm - 11:32 pm
SJU
-
COS
12h 01m
2 stops
$355American Airlines
Sat, May 2 - Sat, May 9
Southwest Logo
6:20 am - 3:35 pm
COS
-
SJU
7h 15m
1 stop
Southwest Logo
11:15 am - 8:45 pm
SJU
-
COS
11h 30m
2 stops
$358Southwest
Tue, May 12 - Tue, May 19
Southwest Logo
12:40 pm - 11:40 pm
COS
-
SJU
9h 00m
2 stops
Southwest Logo
8:10 am - 8:15 pm
SJU
-
COS
14h 05m
2 stops
$370Southwest
Mon, Apr 27 - Thu, Apr 30
United Airlines Logo
5:13 pm - 1:11 pm
COS
-
PUJ
17h 58m
2 stops
United Airlines Logo
1:25 pm - 8:53 pm
PUJ
-
COS
9h 28m
1 stop
$513United Airlines
Sat, May 9 - Tue, May 19
United Airlines Logo
3:25 pm - 1:11 pm
COS
-
PUJ
19h 46m
2 stops
United Airlines Logo
1:25 pm - 8:53 pm
PUJ
-
COS
9h 28m
1 stop
$533United Airlines
Wed, Jul 15 - Wed, Jul 22
Delta Logo
6:00 am - 2:41 pm
COS
-
PLS
6h 41m
1 stop
Delta Logo
2:10 pm - 9:22 pm
PLS
-
COS
9h 12m
1 stop
$703Delta
Wed, Apr 22 - Sun, Apr 26
Delta Logo
7:59 am - 12:00 pm
COS
-
GCM
27h 01m
2 stops
Delta Logo
1:25 pm - 8:20 pm
GCM
-
COS
7h 55m
1 stop
$919Delta
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 ($282) and Southwest ($358).

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 4307 reviews
8.0Comfort
8.1Boarding
8.6Crew
7.0Food
7.5Entertainment
Airline reviews

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

4.0 OkayEmma, Mar 2026
LAX - PHX
Read more Southwest reviews

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

Mediocre. Boarding is now unpleasant. The employees, once friendly and nice, are now regularly speaking sternly to passengers, badgering them to do things right so they can take off on time and gate check bags because they don't have enough overhead bin space. The pretzel snack was crushed flat and broken into even smaller pieces, which happens frequently lately. Drink service was suspended before they reached my row.

The last 3 flights between BWI and BDL canceled the beverage service mid- way. Just say up front that the fight is too short. Thanks!

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.

The whole experience was excellent. As it most often is with Delta

Cabin was not pressurized properly. Several passengers had respiratory difficulties.

I was happy that I was able to get a last minute flight but unfortunately my seat was a middle seat. Even with Delta Comfort I wasn't comfortable

There’s not much to say about a one hour flight. This is a connection from LA to RNO that I missed the previous night due to a mechanical check delay on my originating flight from JFK to LAX. The short flight itself was fine. Instructions from the pilot and crew were per usual. The coffee was barely lukewarm, which possibly was purposeful so we would down it quickly. Bags were already on carousel upon reaching baggage claim, which was excellent.

Flight was warm for first few hours and quite rough

Seat was extremely hard which made even a short 1 hour 20 minute flight fairly uncomfortable.

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.

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..

Snow delayed boarding several times, which I understand happens. Issue I had was that after we did board, pilot told us we were going to roll out to be de-iced, then on our way. We were de-iced once, taxied to the tarmac and then stopped. Sat for another 30 minutes or so, the another de-icing. Then we rolled out to a parking spot, only to sit for another hour due to a traffic stop in DCA, which I'm confident they knew would happen before we boarded. Pilot gave no updates other than we had to hold, attendants did speak to the crew, but when asked, said the pilot would be updating us. We on the ground in the plane waiting for over 2 hours. They did communicate that bathrooms would be open, but no other news until we left. Would have been better to be up front about status.

Good crew and flight was on time. It’s a small plane with limited overhead luggage space. They said the overhead space was full and I had to check my bag. There was still space when I got on. Waiting for my checked luggage added 30 minutes to my trip. Not the end of the world but also not great.

My seat was assigned last row behind restrooms No legroom’s I’m very Pettit Still was not comfortable Food choice was excellent

Delayed initially because they couldn’t print the flight details. Poor instruction on delay. When I got on the plane the flight attendant argued with me about whether my carry on would fit (it did, although she didn’t acknowledge that). No greeting (other than arguing with me) getting on or off the plane.

Overall good. The pilots and flight attendants are excellent! The equipment was the issue on my First flight as they had to wait for a part to be installed. So the take off was at least 30 minutes later.

The worst Airline ever. They centered my second flight and leave me in NY. They don’t have any representatives at the airport and they don’t respond to calls. Basically I got stuck. I will never purchase through there again.

It was an older plane. First Class was not especially roomy or comfortable. It was a short flight so there were no meal but they did offer mixed nuts which used to be normal but now is rare. Crew member was very polite and professional.

The chicken wrap was tiny ($13 for what looked like a 1/3 of a normal wrap?) and disgusting.

It was a train wreck but on an airplane. First off, flight was delayed then we board only to hear two announcements, First weather delays in Orlando and second backup battery warning on emergency lights. After sitting on the plane for almost 2 hours they have us deplane due to the maintenance issue. We were told they were getting another plane. In the mean time, I notice another American- Orlando flight and ask the gate agent if I can switch. He says he cant help me and I'd have to walk to A13 from A37. Really!? I get down there and get a seat only to get an announcement my original flight was RE-boarding. The Then inflight there's no communication and I notice on flightaware were circling over the Gulf of America. I call the flight attendant and of course she has no clue and apparently 5m later the pilot finally tells us about another delay. Why does American always have these service and delay issues? They are my LAST choice in flights now!

Mediocre would be best description. Food bland. Seat biz class uncomfortable to sleep. Crew never dimmed lights completely in an overnight flight to Europe. Would avoid AA if possible.

Everything you need to know for your flight to Caribbean

Information on your arrival and departure airports