$133 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 2/10. 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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Flight Deals

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$441
Santo Domingo
Santo Domingo2 stops$501
Montego Bay
Montego Bay2 stops$509
Oranjestad
Oranjestad2 stops$872
Nassau
Nassau2 stops$537
Kingston
Kingston2 stops$709
Providenciales
Providenciales2 stops$768
Bridgetown
Bridgetown2 stops$597
George Town
George Town1 stop$491
Aguadilla
Aguadilla2 stops$602
Punta Cana
Punta Cana2 stops$441
Santo Domingo
Santo Domingo2 stops$501
Montego Bay
Montego Bay2 stops$509
Oranjestad
Oranjestad2 stops$872
Nassau
Nassau2 stops$537
Kingston
Kingston2 stops$709
Providenciales
Providenciales2 stops$768
Bridgetown
Bridgetown2 stops$597
George Town
George Town1 stop$491
Aguadilla
Aguadilla2 stops$602

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

di, feb. 17 - di, feb. 24
American Airlines Logo
11:49 am - 10:00 am
COS
-
SJU
19h 11m2 stops
American Airlines Logo
7:00 am - 4:00 pm
SJU
-
COS
12h 00m2 stops
$266American Airlines
di, mrt. 3 - di, mrt. 10
American Airlines Logo
1:59 pm - 11:56 am
COS
-
SJU
18h 57m2 stops
American Airlines Logo
6:00 am - 8:37 pm
SJU
-
COS
16h 37m2 stops
$349American Airlines
za, mei. 2 - di, mei. 5
United Airlines Logo
10:30 am - 11:50 pm
COS
-
SJU
11h 20m2 stops
United Airlines Logo
1:00 am - 10:41 am
SJU
-
COS
11h 41m2 stops
$356United Airlines
ma, apr. 20 - za, apr. 25
American Airlines Logo
1:39 pm - 4:32 am
COS
-
SJU
12h 53m1 stop
American Airlines Logo
11:59 pm - 12:45 pm
SJU
-
COS
14h 46m1 stop
$378American Airlines
ma, jan. 26 - vr, jan. 30
American Airlines Logo
6:12 am - 11:59 pm
COS
-
SJU
14h 47m2 stops
American Airlines Logo
6:00 am - 5:41 pm
SJU
-
COS
14h 41m2 stops
$384American Airlines
di, mei. 26 - ma, jun. 1
United Airlines Logo
7:30 am - 5:30 pm
COS
-
SJU
8h 00m1 stop
United Airlines Logo
2:05 am - 1:11 pm
SJU
-
COS
13h 06m2 stops
$412United Airlines
wo, jan. 28 - wo, feb. 4
Delta Logo
7:59 am - 3:20 pm
COS
-
BGI
28h 21m2 stops
Delta Logo
4:30 pm - 10:23 pm
BGI
-
COS
32h 53m2 stops
$597Delta
di, apr. 21 - di, apr. 28
Delta Logo
6:20 am - 3:29 pm
COS
-
MBJ
8h 09m1 stop
Delta Logo
12:55 pm - 8:19 pm
MBJ
-
COS
8h 24m1 stop
$669Delta
ma, mrt. 2 - do, mrt. 5
Air Canada Logo
1:40 pm - 2:35 pm
COS
-
BGI
21h 55m2 stops
Air Canada Logo
4:55 pm - 8:49 am
BGI
-
COS
42h 54m2 stops
$971Air Canada
ma, mrt. 2 - do, mrt. 5
Air Canada Logo
1:40 pm - 2:35 pm
COS
-
BGI
21h 55m2 stops
Air Canada Logo
4:55 pm - 8:49 am
BGI
-
COS
42h 54m2 stops
$972Air Canada
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.

What is the cheapest month to fly from Colorado Springs to Caribbean?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Colorado Springs to Caribbean, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Colorado Springs to Caribbean is November, when tickets cost $463 (return) on average. On the other hand, the most expensive months are March and August, when the average cost of round-trip tickets is $704 and $641 respectively.

Good to know

Low seasonSeptember
Cheapest flight$133
Best time to beat the crowds with an average 27% drop in price.
Most popular time to fly and prices are also 8% lower on average.
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 4254 reviews
8.1Boarding
7.5Entertainment
8.6Crew
7.0Food
8.0Comfort
Airline reviews

We got exit row seats both flights. Everything was running on time

10.0 ExcellentMaggie, Jan 2026
FAT - LAS
Read more Southwest reviews

We got exit row seats both flights. Everything was running on time

The flight crew was extremely rude and especially not helpful when our flight was delayed.

Pretty seamless, just a tad bit late in taking off and landing.

Flight was fine other than there was a gate change that I was not notified of. By chance I happened to check my phone and saw the change, otherwise, we would have missed our connecting flight.

Haven’t flown on SW in years. Flight was on time departing and arriving. Served vegan butter onion flavored pretzels which were bad. Coke served was in a tiny paper cup. Crew was not engaging. Felt like they were going through the motions. Old plane, tight seats and no leg room.

Check-in, Boarding and flight were smooth. All the employees and crew was very nice and funny. They gave the kids crayons and workbooks to keep them occupied which was a big win. I’ve flown Southwest many times and that’s the first time I’ve seen that and it is a great addition.

Flight was on time. Wi-fi was a little spotty/slow. Boarding and exit were efficient.

Okay, not wonderful. Short flight. Wi-fi didn't work properly. Stuck waiting for a gate to open upon arrival for 20 or so minutes.

They sent a notice that they were boarding an hour early. We had to leave the club and run to the gate. They said sorry, that came from corporate and was a mistake. They did not have enough seating because the flight before it had not taken off on time. They moved our gate and delayed it for an hour.

The boarding and seat assignment system no longer works for me, but I know it is being replaced. Otherwise, I am good with the overall experience.

Food is basically Sun Chips, cookies or Cheezits. I had an exit row seat so I had plenty of room. The crew was very nice and efficient. Pilot kept us informed. Pretty good flight.

Air travel sucks. It continues to be awful for all airlines. No shame on delta alone.

It was Delta, but the flight attendants were stressful and disrespectful. I am a diamond member a travel weekly. I have not had a negative thing to share in quite some time. But this was noticeable.

Comfort Plus seat 11E seemed smaller than prior flights. The movie selection is good. Watched most of the most recent Tron movie. I'll watch the remaining part later as my movie is saved in the Delta Seatback Experience.

Flight was late from Newark to Atlanta, I asked flight attendant to please let my family of 3 out first when we landed to Atlanta because we were late for our connecting flight to Quito. She didn't and we were late for 5 minutes we couldn't board the plane and spend hours trying to get another flight with customer service for the next day.

I really liked the legroom. I am 6’4”.a at For some reason our seats were not together and using the app to fix it didn’t work. Passengers were nice enough to move for us but you should absolutely ensure a parent sits with their child.

Late delayed flight delays boarding and delays leaving and delays on arrival too. Cramped plane no room no food.

DTW line is too long. The flights from DTW to BWI are always delayed for unknown reasons.

Delta canceled our flight and we had to scramble to find another airline to get home. Phoenix is not a delta hub so they didn’t have another plane. It would have been a red eye though Salt Lake City. Getting in at 5am. No bueno.

This flight was no comparison to our prior flight. I'm thinking it all has to do with the age of the aircraft.

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.

Impressed with the service despite turbulence because of the weather. Both flights arrived before their scheduled times.

The flight was good. We had to spend almost an hour on the tarmac when we arrived in Dallas. Waiting for a gate. What’s the point of arriving early if you have no gate to park at?

Lower WiFi prices; allow us to see our flight on a map; more variety of drink choices.

So excited very proud first of all I wanna thank kayak all updates very professional and fast alart And amazing cabin crew so nice to me they deserve big salute

UGH I HAD TO MISS MY FIRST FLIGHT TO TAMPA CAUSE OF THE 10 MINUTE DELAY OF THE ORLANDO TO MIAMI ONE SO THEY HAD ME GET ANOTHER TICKET. I AM NOT HAPPY AT ALL BECAUSE IT MADE ME MISS MY CONNECTING FLIGHT FROM TAMPA TO LONDON AND FORCED ME TO MISS A DAY AT MY ROOM IN THE UK.

Wish they didnt delay off-boarding for 10 minutes so i could connect to my flight from miami to tampa

We experienced gate changes and a long delay. My seat was dirty when I boarded and I had to use wipes to clean it myself. There was an unpleasant and overpowering cleaning product scent on the plane as well that lingered through the flight.

Seats were much more cramped then on the 737. Narrower and rows closer together. Flight was absolutely packed and the plugs under the seats didn't work. Was forced to check my bag even though previous flight had no issue with it.

Good food & refreshment. The seats and entrainment screens are modern compared to others. The staff though pleasant serve and attend to passengers based on nationality. Some get served first others last regardless of their seating positions.

It was fine. My connection in Charlotte to go to WPB was too late and I had to spend the night in the Charlotte Airport in the mini suites.

The flight was on time and arrived early. The crew were friendly and helpful.

Everything you need to know for your flight to Caribbean

Information on your arrival and departure airports