$192 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 1/14. 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$466
Santo Domingo
Santo Domingo2 stops$398
Montego Bay
Montego Bay1 stop$490
Oranjestad
Oranjestad2 stops$516
Nassau
Nassau2 stops$669
Kingston
Kingston2 stops$708
Providenciales
Providenciales2 stops$660
Bridgetown
Bridgetown2 stops$596
George Town
George Town1 stop$490
Aguadilla
Aguadilla2 stops$709
Punta Cana
Punta Cana2 stops$466
Santo Domingo
Santo Domingo2 stops$398
Montego Bay
Montego Bay1 stop$490
Oranjestad
Oranjestad2 stops$516
Nassau
Nassau2 stops$669
Kingston
Kingston2 stops$708
Providenciales
Providenciales2 stops$660
Bridgetown
Bridgetown2 stops$596
George Town
George Town1 stop$490
Aguadilla
Aguadilla2 stops$709

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

Tue, Jan 27 - Tue, Feb 3
American Airlines Logo
3:17 pm - 10:48 am
COS
-
SJU
16h 31m2 stops
American Airlines Logo
6:00 am - 5:41 pm
SJU
-
COS
14h 41m2 stops
$265American Airlines
Wed, Apr 29 - Fri, May 1
American Airlines Logo
1:39 pm - 9:13 am
COS
-
SJU
17h 34m2 stops
American Airlines Logo
11:59 pm - 4:15 pm
SJU
-
COS
18h 16m1 stop
$348American Airlines
Wed, Jan 21 - Fri, Jan 23
United Airlines Logo
7:30 am - 12:36 am
COS
-
SJU
14h 06m2 stops
United Airlines Logo
2:05 am - 2:34 pm
SJU
-
COS
15h 29m2 stops
$355United Airlines
Wed, Jan 21 - Sat, Jan 24
Delta Logo
1:20 pm - 11:45 pm
COS
-
SJU
7h 25m1 stop
Delta Logo
6:15 am - 12:23 pm
SJU
-
COS
9h 08m1 stop
$375Delta
Fri, Feb 6 - Sun, Feb 8
Multiple Airlines Logo
10:30 am - 5:00 pm
COS
-
SJU
27h 30m2 stops
Multiple Airlines Logo
5:16 pm - 9:40 am
SJU
-
COS
19h 24m1 stop
$378Multiple Airlines
Tue, May 12 - Wed, May 20
Delta Logo
6:00 am - 8:06 pm
COS
-
SJU
12h 06m1 stop
Delta Logo
6:15 am - 12:59 pm
SJU
-
COS
8h 44m1 stop
$403Delta
Mon, Jan 12 - Thu, Jan 15
American Airlines Logo
6:12 am - 10:26 pm
COS
-
SJU
13h 14m1 stop
American Airlines Logo
6:00 am - 2:09 pm
SJU
-
COS
11h 09m2 stops
$407American Airlines
Mon, Jan 26 - Wed, Jan 28
United Airlines Logo
5:50 am - 6:25 pm
COS
-
SJU
9h 35m1 stop
United Airlines Logo
2:25 pm - 10:06 pm
SJU
-
COS
10h 41m1 stop
$414United Airlines
Mon, Mar 2 - Thu, Mar 5
Air Canada Logo
1:40 pm - 2:35 pm
COS
-
BGI
21h 55m2 stops
Air Canada Logo
4:55 pm - 11:56 pm
BGI
-
COS
34h 01m2 stops
$818Air Canada
Mon, Mar 2 - Thu, Mar 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
$884Air 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 $734 and $641 respectively.

Good to know

Low seasonSeptember
Cheapest flight$192
Best time to beat the crowds with an average 27% drop in price.
Most popular time to fly and prices are also 9% 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 4251 reviews
7.0Food
8.1Boarding
8.6Crew
8.0Comfort
7.5Entertainment
Airline reviews

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.

8.0 ExcellentMaggie, Dec 2025
BWI - LAS
Read more Southwest reviews

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.

The lead steward kept singing about "San Francisco" and hotel California---more annoying than humorous....needs work. Flight was smooth and on time.

Still a fan of open seating. Flight was on schedule and arrived on time. The 737 MAX is very comfortable.

Airline travel is always too cramped to really be pleasant, but the cabin crew on this flight did a pretty good job of making up for it by putting on some music during boarding and sprinkling a few funny remarks into the safety briefing and announcements, and just generally being friendly and helpful. It definitely reminded me of why I prefer the in-flight experience on Southwest!

A 12 hour flight during the day with one real meal service - are you kidding? Also the breakfast was one of the worst and not what was listed

Flight was delayed several times. At one point, they "pulled back" 15 minutes from the delayed boarding and sent a text saying we would board sooner than previously advised. The flight then was delayed again. And when we boarded, there was an unspecified technical issue which had us waiting in the plane for about an hour.

Delta is a good airline. I've never had an issue with Delta. I'll continue to fly with them until they show me that I shouldn't.

The only thing nice I can say is the flight crew was really nice and apologetic about the situation. They shared as much information as they had and advised us on what we could do about missing connecting flights. The boarding process was so slow. The gate agent was working by herself and should have had someone working with her. It took almost an hour to board because she was trying to board a full flight of people and provide customer service to everyone who was flying standby and/or had questions. It was really chaotic. This didn't help the fact that we were delayed and folks were missing connections the longer it took.

The gate attendants and the crew were terrible. Because of high winds, they needed to carry more fuel, so they had to get volunteers to take the next flight at 6 am the next day. They did a terrible job of it - our flight ended up taking off just under 3 hours of the scheduled time. I hope to never fly Delta again.

Did not realize internet screen was hidden between seats and no info printed!!!!

2 of the seats in row 31 the entertainment system was not working, and one seat the tray table did not go all the way down. Flight arrived early and departed on time which was great.

Very good flight crew and very nice people staff were incredible especially the gate agent

Waited at the usual crowded gate at DCA where one ends up standing up because there aren't enough seats.

The flight was delayed for about 2 hrs. Other than it, it was good.

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 very smooth and the meal in business class was great.

The captain brought my 6 year old son into the cockpit and allowed him to ask questions, sit in the captain’s chair and talk about all the gears and levers. Made the trip very special for him.

I take this flight about 6-8 times per year. It is convenient and saves an hour or two by skipping PDX, SEA, PHX, or ORD (but it takes longer to get bags to the carousel than Alaska Airlines). I wish the food service were better (but they might cut back on it because it is a red-eye). The WifI seems to go down about an hour out of Anchorage, and then comes back about an hour later...so be warned if this is an issue for you.

Better service. No food options, but we did get drinks and a cookie.

Boarding was organized and timely. Food was mediocre, especially for first class travel.

We were 4+ hours delayed. AA is absolutely obnoxious. They just kept pushing back the time to the point where we did not get into Vegas until after midnight when we were supposed to arrive like 845pm.

My last flight on 25 Dec, it’s Christmas Day, everyone happy and very good mood. I really enjoy traveling with Americans Airlines from Miami to Minneapolis my home town after long flight from lhe to Doha then Miami. Thank you again to make my travels comfortable and relaxed. Best regards

The boarding process needs to be fixed. The zone don't work, especially when there is hardly anyone in zones 3, 4,and 5, leaving the majority of the passengers backed up in the aisle, especially because passengers seated near the front are blocking passengers who are seated in the rear of the plane. It would also help if the size of carry on bags was more strictly enforced.

I requested a low sodium meal. Reason being, I take medicine for high blood pressure and I wear compression socks on long flights to help with leg swelling. Having less sodium in meals really helps me feel better on long flights. I received my initial low sodium meal after takeoff. Just before landing, the crew came through with the meal cart and offered me what was being served. I said no thank you and then noticed my low sodium meal in the meal cart, with my name and seat assignment on it. I motioned to the crew member, but he grabbed the meal cart and proceeded to move to the rear of the aircraft. He didn’t see me or other passengers who had attempted to get this attention. He was more concerned about completing meal service since we were due to land in under 45 minutes. I pressed the call light five times from my seat to receive help, but no crew member responded to me. So, I didn’t receive a second meal, one that I requested (the low sodium option). This led me to have a migraine from only eating one meal on an 11-hour flight. This is why I’m not a fan of flying US-based airlines overseas. The crew members continue to show the absolute worst customer service experience. I would not recommend flying American for overseas flights.

WiFi didn’t work the entire flight. Very disappointing. Minimal food and options - sadly the state of current affairs. All other aspects of the flight were fine.

Everything you need to know for your flight to Caribbean

Information on your arrival and departure airports