$186 Find Cheap Flights from Colorado Springs to Caribbean - Compare and Save

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 8/25. 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.
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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 Cana1 stop$676
Santo Domingo
Santo Domingo2 stops$675
Montego Bay
Montego Bay1 stop$457
Oranjestad
Oranjestad2 stops$812
Nassau
Nassau1 stop$470
Kingston
Kingston2 stops$745
Providenciales
Providenciales2 stops$900
Bridgetown
Bridgetown2 stops$1,632
George Town
George Town2 stops$528
Aguadilla
Aguadilla2 stops$472
Punta Cana
Punta Cana1 stop$676
Santo Domingo
Santo Domingo2 stops$675
Montego Bay
Montego Bay1 stop$457
Oranjestad
Oranjestad2 stops$812
Nassau
Nassau1 stop$470
Kingston
Kingston2 stops$745
Providenciales
Providenciales2 stops$900
Bridgetown
Bridgetown2 stops$1,632
George Town
George Town2 stops$528
Aguadilla
Aguadilla2 stops$472

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, Aug 25 - Fri, Aug 28
Southwest Logo
10:45 am - 10:00 pm
COS
-
SJU
9h 15m
2 stops
Southwest Logo
5:30 am - 3:40 pm
SJU
-
COS
12h 10m
2 stops
$372Southwest
Tue, Aug 25 - Fri, Aug 28
Delta Logo
6:00 am - 4:38 pm
COS
-
SJU
8h 38m
1 stop
Delta Logo
2:59 pm - 9:38 pm
SJU
-
COS
8h 39m
1 stop
$376Delta
Wed, Sep 2 - Fri, Sep 11
American Airlines Logo
12:37 pm - 11:15 pm
COS
-
SJU
8h 38m
1 stop
American Airlines Logo
6:00 am - 10:55 pm
SJU
-
COS
18h 55m
2 stops
$377American Airlines
Tue, Aug 25 - Sat, Aug 29
Southwest Logo
6:15 am - 7:00 pm
COS
-
SJU
10h 45m
2 stops
Southwest Logo
8:20 am - 5:55 pm
SJU
-
COS
11h 35m
2 stops
$406Southwest
Sun, Aug 23 - Sat, Aug 29
Southwest Logo
11:00 am - 12:30 am
COS
-
SJU
11h 30m
2 stops
Southwest Logo
5:05 am - 3:30 pm
SJU
-
COS
12h 25m
2 stops
$408Southwest
Sat, Aug 15 - Thu, Aug 20
United Airlines Logo
7:40 am - 8:38 pm
COS
-
SJU
10h 58m
1 stop
United Airlines Logo
1:25 pm - 11:55 pm
SJU
-
COS
12h 30m
2 stops
$425United Airlines
Sun, Oct 11 - Mon, Oct 12
United Airlines Logo
5:30 am - 5:38 pm
COS
-
SJU
10h 08m
1 stop
United Airlines Logo
2:55 pm - 11:59 pm
SJU
-
COS
11h 04m
2 stops
$428United Airlines
Tue, Oct 13 - Thu, Oct 22
United Airlines Logo
7:40 am - 8:38 pm
COS
-
SJU
10h 58m
1 stop
United Airlines Logo
2:00 pm - 10:06 pm
SJU
-
COS
10h 06m
1 stop
$429United Airlines
Sun, Aug 23 - Sat, Aug 29
United Airlines Logo
7:40 am - 8:38 pm
COS
-
SJU
10h 58m
1 stop
United Airlines Logo
2:00 pm - 8:44 pm
SJU
-
COS
8h 44m
1 stop
$446United Airlines
Tue, Sep 29 - Fri, Oct 16
American Airlines Logo
4:08 pm - 11:00 am
COS
-
SJU
16h 52m
2 stops
American Airlines Logo
4:17 pm - 9:37 am
SJU
-
COS
19h 20m
1 stop
$452American Airlines
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 October, when tickets cost $420 (return) on average. On the other hand, the most expensive months are March and February, when the average cost of round-trip tickets is $736 and $639 respectively.

Good to know

Low season

November

Cheapest flight

$186
Best time to beat the crowds with an average 3% drop in price.
Most popular time to fly with an average 5% 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 3 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 4242 reviews
8.1Boarding
7.5Entertainment
8.0Comfort
7.0Food
8.6Crew
Airline reviews

The flight was late. The crew was rude. There was no food. Cramped and uncomfortable. Nothing about this flight was good.

2.0 MediocreIrene, Jun 2026
DEN - SFO
Read more Southwest reviews

The flight was late. The crew was rude. There was no food. Cramped and uncomfortable. Nothing about this flight was good.

It was great. The gate staff were very helpful in Portland when my son forgot his rolling bag and had to go back to get it just in time to make it on the plane. We really appreciate that. Great job!

This leg was much better, but we did have to have a 3 hour lay o er after coming from a very exhausting hiccup with our flight from BNA to Den

Southwest is kind of a slum airline. It’s gotten more expensive over the years for less and less service. I am a Southwest Chase Visa card holder and was forced to choose a seat in the 26th row in the middle seat. However my wife who is a rewards member but doesn’t hold a card or anything else, gets randomly assigned a normally paid seat in row 6! How does that work?

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.

Everything went smoothly and we even arrived a little bit early.

Connecting flight is on time and boarding was a breeze!

Great no problem boarding suitcase on time for pick up

Delay after delay after delay. Very disappointing I am about ready to give up on Southwest. One of the crewmembers sat and played games on her phone for the entire trip from Chicago to Baltimore. Unbelievable, very unprofessional, and very disappointing.

I've never flown Southwest before and I can say its my new favorite airline.

Flight was delayed “due to earlier delays of that plane”, so we were nearly three hours late.

I needed internet for critical matters and it never worked.

Very easy ! Use the kiosk and bag drop and right to security within 10 min

The entertainment they offer could use some games, and maybe they could add some cookies to the snack menu. And the automated messages are a bit repetitive. But it was comfortable temperature wise and the seats were comfortable. The crew is very polite and helpful

This planes staff was top tier. Everything went great and had a great flight home.

Both of my flights arrived early and check in process was smooth

Overall poor for me I paid extra for seats with leg room and my regional flights exit row seats have less leg room then the others that's money that could have been saved and on my final flight home the flights air was not operating it was unbearably hot in the cabin I will be contacting United and filing a DOT complaint

Flight home lot's of room shame I never noticed that they ripped my suitcase and didn't notice it to I got toy destination and had to buy new set

It was delayed several hours which delayed our connection in Denver. Not happy.

Ridiculous delays with weak excuses. United needs to do their job and troubleshoot. The rate they charge demands no less. Planes are way too full and seats are cramped. Charging for seats and luggage adds insult to injury.

The flight attendants were extremely sourly and borderline rude. I did not feel appreciated as an AA customer once.

The airplane seats were spacious and comfortable, and the flight attendants were friendly and attentive. The food was delicious like never before. The blankets and toiletries were thoughtfully provided. The captain's navigation was steady and reliable. In short, having flown with Starlux, I won't consider any other airline next time.

As we approached Denver, we encountered quite a bit of turbulence. I know this can sometimes be the case as I frequently fly this route but not on American. My gripe: Usually a pilot or co-pilot alerts passengers to the possibility of turbulance ahead of time. This did not occur nor did he communiucate during what was a pretty rough ride.

American flight was diverted and delayed but app didn’t show that information so I wasn’t able to change my connection until the last min.

Our flight from Eagle to Vail was delayed to the point we missed our connection to Savannah. Now we’re a family of 4 in a hotel room with luggage, no toiletries, no clean clothes. Gate attendant said the delay was mechanical but it was put in the system as something else so no compensation. That’s just wrong.

Terrible. Our luggage was delayed and couldn’t be delivered for several days. We got bad information from the airline agents at baggage claim. We had to pick up our car so we wouldn’t be charged for an extra day. We got lost in the maze of airport parking. The baggage claim agents didn’t offer us any compensation for our extra time and expense. We are tired, hungry and very frustrated.

Full flight so overhead bin space ran out & bags had to be checked. When you’re in the last boarding group, you might as well expect that. Don’t pay to check bags though because when they run out of space for carry-ons, they check your bag to your destination for free. When traveling with children, no need to pay extra for seats, they will assign seats & have to sit your children with you.

Don’t know they cancelled the flight day before I was to leave. They sent a email at 9:00 pm at night saying they cancelled. That is the smooth way to say we don’t want your business! I think they didn’t have enough people booking so they cancelled the flight! It’s all about the money anymore there is no honesty in business.

Mechanical delay and no compensation. Missed connection as a result of their delay. Mediocre performance and service. Horrible airline currently with horrible culture.

Any sort of gluten free snack option would be nice

Everything you need to know for your flight to Caribbean

Information on your arrival and departure airports