$141 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 3/10. 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$493
Santo Domingo
Santo Domingo2 stops$538
Montego Bay
Montego Bay2 stops$357
Oranjestad
Oranjestad2 stops$781
Nassau
Nassau2 stops$534
Kingston
Kingston1 stop$480
Providenciales
Providenciales2 stops$688
Bridgetown
Bridgetown2 stops$894
George Town
George Town2 stops$792
Aguadilla
Aguadilla2 stops$850
Punta Cana
Punta Cana1 stop$493
Santo Domingo
Santo Domingo2 stops$538
Montego Bay
Montego Bay2 stops$357
Oranjestad
Oranjestad2 stops$781
Nassau
Nassau2 stops$534
Kingston
Kingston1 stop$480
Providenciales
Providenciales2 stops$688
Bridgetown
Bridgetown2 stops$894
George Town
George Town2 stops$792
Aguadilla
Aguadilla2 stops$850

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

Mon, Apr 13 - Wed, Apr 22
American Airlines Logo
5:41 am - 11:02 pm
COS
-
SJU
15h 21m
1 stop
American Airlines Logo
11:59 pm - 4:23 pm
SJU
-
COS
18h 24m
1 stop
$282American Airlines
Sat, May 2 - Fri, May 8
United Airlines Logo
7:30 am - 8:38 pm
COS
-
SJU
11h 08m
1 stop
United Airlines Logo
1:00 am - 11:05 am
SJU
-
COS
12h 05m
2 stops
$311United Airlines
Thu, Apr 23 - Fri, May 8
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
$350American 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
$357American Airlines
Thu, Apr 2 - Thu, Apr 9
American Airlines Logo
4:48 pm - 12:27 pm
COS
-
MBJ
18h 39m
2 stops
American Airlines Logo
2:29 pm - 9:27 am
MBJ
-
COS
19h 58m
2 stops
$357American Airlines
Sat, May 2 - Fri, May 8
United Airlines Logo
10:40 am - 11:50 pm
COS
-
SJU
11h 10m
2 stops
United Airlines Logo
1:00 am - 2:24 pm
SJU
-
COS
15h 24m
2 stops
$372United Airlines
Sat, May 2 - Fri, May 8
United Airlines Logo
10:40 am - 11:50 pm
COS
-
SJU
11h 10m
2 stops
United Airlines Logo
1:00 am - 11:05 am
SJU
-
COS
12h 05m
2 stops
$390United Airlines
Tue, Jun 2 - Mon, Jun 8
Delta Logo
1:55 pm - 12:18 pm
COS
-
PUJ
20h 23m
2 stops
Delta Logo
1:45 pm - 12:59 pm
PUJ
-
COS
25h 14m
2 stops
$624Delta
Mon, Mar 2 - Mon, Mar 9
Delta Logo
7:55 am - 12:45 pm
COS
-
PLS
26h 50m
2 stops
Delta Logo
2:15 pm - 8:28 pm
PLS
-
COS
8h 13m
1 stop
$798Delta
Sat, Jun 20 - Fri, Jun 26
Delta Logo
6:00 am - 2:40 pm
COS
-
PLS
6h 40m
1 stop
Delta Logo
2:10 pm - 9:22 pm
PLS
-
COS
9h 12m
1 stop
$1,050Delta
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 United Airlines ($311).

Good to know

Low seasonSeptember
Cheapest flight$141
Best time to beat the crowds with an average 26% drop in price.
Most popular time to fly with an average 7% 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 4293 reviews
8.6Crew
7.5Entertainment
8.1Boarding
7.0Food
8.0Comfort
Airline reviews

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.

4.0 OkayAnonymous, Feb 2026
BOI - LAS
Read more Southwest reviews

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.

Only downside was the legroom and seat width, which is always a problem unless I spend more for a premium seat.

My flight from Denver to Minneapolis was excellent. My flight from Minneapolis to Denver was one of the worst I flights I have ever experienced. I had a window seat, the gentleman in the middle seat was morbidly obese and SW should have made him purchase two seats. His elbow dug into my arm most of the way even after I asked to please be careful. I was literally squashed between the him and the window with no wiggle room. The plane was full so it was not possible to ask for a different seat. I realize I should have complained to the flight attendant but I didn't feel anything could be done to rectify the situation. I fly SW often, I will continue to do so as this was my first negative experience.

I was assigned seat 7E, yet my boarding was Group 5, which caused me to have to put my luggage in the back of the plance above `19 or 20 aisle, as passengers who had boarded earlier took the overhead bins in the front. SW needs to monitor bin space and ensure that bin space above the seat are aligned to those sitting near their seats. Also the seating assignments needs to align with group number. Maybe board those last first and so on? Having said the ALL the passengers on the plane were gracious enough to allow me and other passengers in this dilema to retrieve our luggage and helped us along the way. I always love the flight staff, as always their fantastic and I can't rave about them enough!

I appreciate the staff who allowed me to board though I arrived a little late! Regarding the assigned seating, I had booked my flight before this change and wasn't aware of the change at the time, and so I didn't select a seat at booking as I didn't realize it was relevant. Better communication about the change would have been helpful for preparing.

Flight attendants very hospitable and friendly. Pilot flew a smooth take off and landing.

First flight out and was 85 minutes delayed. Notification came out way too late

Delta flights recently are always delayed AND at jfk tney get the gates further away (need To walk 20’ to get to them/all the way at the end of the terminal). Not sure whats happening but price doesnt match experience!

Everything I mentioned earlier - the airbus was more comfortable indeed and the experience was further enhanced.

Delta continues to set the benchmark for traveler-friendly service with minimal disruption and clear communication within the mainland US (coast to coast). I am consistently pleased to be a Delta customer, and this experience once again met my expectations. There was a brief delay departing from MIA due to a technical issue that required the aircraft to return to the gate. However, the situation was handled professionally and transparently. Fortunately, my planned layover allowed ample buffer time, so the adjustment caused no stress. Overall, another smooth and reassuring experience.

Good experience and the flight landed early. There was no food I had or entertainment.

Flight was delayed and no reasons provided. After the passengers were boarded, the crew made announcement that the captain has jot arrived and he would take another 15 mins. All passengers patiently sat until the captain came and started. Terrible experience!

Flight was delayed. No information on why it was delayed. After we boarded the flight, , the crew made announcement that the captain hs not arrived and he will take 15 mins more to arrive. Passengers were just sitting patiently for the captain to arrive and start, Terrible experience.

Totally worth the miles to upgrade to Delta Comfort. Plenty of legroom.

This was my first time flying Delta ever and I had a great experience!

Smallest leg room I've ever had on a plane.

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..

I never flew. Flight was canceled. DIA worst airport in the country. Avoid at all costs.

No Snacks or Entertainment. The flight was short, snacks should still be given.

We lost a day of our vacation because AA did not get the plane to the gate on time. Even though the gate attendant was very clear that it was not weather related, AA would do nothing because there was some snow that day. They basically said the gate attendant was wrong even though she was on the front line of the situation and they were not.

See prior comment about how Kayak mishandled my reservation and delayed my arrival by 6 hours.

American Airlines was great and worked very hard to change my ticket so I could get an earlier, direct flight back to Dallas. However, I was informed that Kayak made mistakes with my itinerary and classified my ticket as desiring to be on the earlier flight instead of taking the necessary step of calling AA to get me on the standby list. This ended up keeping me from being added to the standby list and delayed me getting home by 6 hours. I am happy to discuss this further with Kayak so they can correct their procedures so this won't happen again.

The flight was fine. It's the satellite terminal that supports American eagle flights is what sucks. There is only one food option and everything there is way overpriced. I mean I know it's airport pricing, but it's even crazier than that. I bought a sandwich in a plastic container for $18.

Overall it was a good flight. Because we traveled on a Saturday we were upgraded to FC since my wife and I are both Executive Platinum. The only areas for improvement we noted are better snack assortment and perhaps a little nicer plane as American is flying some older planes now. Everything else on this flight was excellent, which is frankly not the norm for American since we have had multiple issues on prior AA flights.

The smell from the bathroom kept wafting through the cabin. It made people sick.

The flight was really crowded. Flight attendants were just ok.

Boarding delayed 20 minutes for no reason, no wifi, in flight entertainment, or snacks / waters?

Didn't get a seat assignment until the last minute even though i picked a seat.

Everything you need to know for your flight to Caribbean

Information on your arrival and departure airports