$123 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 9/29. 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

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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$494
Santo Domingo
Santo Domingo2 stops$904
Montego Bay
Montego Bay1 stop$503
Nassau
Nassau2 stops$679
Kingston
Kingston2 stops$935
Providenciales
Providenciales2 stops$548
Bridgetown
Bridgetown2 stops$696
George Town
George Town2 stops$533
Punta Cana
Punta Cana2 stops$494
Santo Domingo
Santo Domingo2 stops$904
Montego Bay
Montego Bay1 stop$503
Nassau
Nassau2 stops$679
Kingston
Kingston2 stops$935
Providenciales
Providenciales2 stops$548
Bridgetown
Bridgetown2 stops$696
George Town
George Town2 stops$533

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, Oct 21 - Mon, Oct 27
American Airlines Logo
6:02 am - 6:25 pmCOS-SJU
10h 23m2 stops
American Airlines Logo
7:00 pm - 9:46 amSJU-COS
16h 46m2 stops
$245American Airlines
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Tue, Oct 21 - Mon, Oct 27
American Airlines Logo
6:02 am - 6:25 pmCOS-SJU
10h 23m2 stops
American Airlines Logo
3:10 pm - 11:44 pmSJU-COS
10h 34m1 stop
$325American Airlines
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Fri, Oct 31 - Sun, Nov 9
 Logo
9:41 am - 2:42 pmCOS-SJU
27h 01m1 stop
 Logo
7:30 am - 10:31 amSJU-COS
30h 01m1 stop
Fri, Oct 31 - Sun, Nov 9
 Logo
9:41 am - 7:14 pmCOS-SJU
31h 33m2 stops
 Logo
7:30 am - 10:31 amSJU-COS
30h 01m1 stop
Thu, Oct 30 - Sun, Nov 9
Southwest Logo
11:10 am - 12:45 amCOS-SJU
11h 35m1 stop
Southwest Logo
6:40 am - 4:35 pmSJU-COS
12h 55m2 stops
$430Southwest
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Fri, Oct 10 - Wed, Oct 15
Southwest Logo
11:10 am - 12:45 amCOS-SJU
11h 35m1 stop
Southwest Logo
7:40 am - 5:35 pmSJU-COS
11h 55m2 stops
$440Southwest
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Fri, Jan 9 - Sun, Jan 18
United Airlines Logo
1:50 pm - 6:12 amCOS-SJU
13h 22m2 stops
United Airlines Logo
2:10 pm - 11:59 pmSJU-COS
12h 49m2 stops
$471United Airlines
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Tue, Oct 21 - Tue, Oct 28
Delta Logo
1:16 pm - 11:23 amCOS-MBJ
21h 07m2 stops
Delta Logo
12:48 pm - 12:11 pmMBJ-COS
24h 23m2 stops
$507Delta
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Mon, Sep 29 - Mon, Oct 6
Delta Logo
5:55 pm - 12:45 pmCOS-PLS
16h 50m2 stops
Delta Logo
2:05 pm - 8:30 pmPLS-COS
8h 25m1 stop
$548Delta
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Fri, Jan 9 - Sun, Jan 18
United Airlines Logo
7:30 am - 6:25 pmCOS-SJU
7h 55m1 stop
United Airlines Logo
8:35 am - 5:24 pmSJU-COS
11h 49m2 stops
$575United Airlines
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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 $469 (return) on average. On the other hand, the most expensive months are December and March, when the average cost of round-trip tickets is $787 and $734 respectively.

What’s the cheapest day of the week to fly from Colorado Springs to Caribbean?

The average price of all round-trip flights from Colorado Springs to Caribbean clicked on KAYAK for each day over the last 12 months.

Your flight ticket price will generally be cheaper if you fly to Caribbean on a Monday and more expensive on a Friday. On your return trip to Colorado Springs, you should consider flying back on a Friday, and avoid Sundays for better deals.

How far in advance should I book a flight from Colorado Springs to Caribbean?

To calculate weekly average prices, KAYAK takes all prices for each week before departure 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 average of all the values for each week.

To get a below average price on the flight from Colorado Springs to Caribbean, you should book around 2 weeks before departure, which saves you about 5% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 18 weeks before departure.

Good to know

Low seasonSeptember
Cheapest flight$123
Best time to beat the crowds with an average 20% drop in price.
Most popular time to fly and prices are also 5% 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.

  • What is the cheapest time of day to fly to Caribbean?

    The cheapest time of day to fly to Caribbean is generally in the evening, when round-trip flights cost $557 on average. Morning departures are around 3% more expensive than evening flights, on average. The most expensive time of day to fly to Caribbean is generally in the morning, which is peak travel time and where the average cost of a ticket is $576.

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 4246 reviews
8.6Crew
8.1Boarding
7.0Food
7.5Entertainment
8.0Comfort
Airline reviews

Near 4 hour flight with only 1 service. Had to use call button to request water. Internet and power not working until into flight. Internet would stop working during flight.

6.0 GoodDavid, Aug 2025MCO - DEN
Read more Southwest reviews

Near 4 hour flight with only 1 service. Had to use call button to request water. Internet and power not working until into flight. Internet would stop working during flight.

Southwest's seats are the least comfortable I have ever sat in.

The cabin was quiet for the redeye flight. The area was clean. The staff was great. The 787 Max was in good condition. Drawbacks were that the seat widths were tight for some passengers. The seat padding was at best average and for a long flight uncomfortable.

Southwest like most American domestic airlines, is a mediocre airline. But it is among the cheapest. Oh well.

My flight was delayed 50 minutes and we were rushed to board to then sit for 15 minutes until the pilot arrived. Unacceptable since we could have waited to board. Also the delayed flight was updated AFTER we boarded to more than the 10 minutes as originally stated.

Other than a bit of a delay, everything was good. Again, the boarding process and picking seats is the only thing I don't enjoy.

If we are going to have to pay for luggage, make it easier to do. Put something on the app during check-in so I don't need to do it at the kiosk. I've done it twice recently and I ended up having to pay at the desk because something went wrong at the kiosk in Tampa.

Better and more food and drinks. Put msnbc and free speech tv on the news channel selection list.

southwest just starting charging for luggage. hadnt realized it until it was too late. now out $70 when i couldve bought a carry on if i wouldve known. free bags was one of the only reasons i chose southwest over another airline (the other being no assigned seats, which is apparently also being changed). stupid business decision. wont be flying southwest anymore.

The quality of Southwest Airlines continues to degrade each time I fly with them. If it were not for the free luggage, I would probably choose another airline. Their prices are a little bit competitive, but way too high for the quality of the service. Southwest is not unique in this way. Domestic flight in the United States of America has continued to be a lower and lower quality product. Very sad when you compare the quality of domestic airlines to that of many international airlines around the world.

Delayed due to thunderstorms and no in-flight service due to rough weather — both of which are out of Delta’s control. Flight was good overall.

The flight attendants in SLC were rude. I arrived 40 minutes early to gate. Ticket said I needed check in for seat assignments and tried check in and attendants said they weren’t doing it. And proceeded to never call me to give me a ticket so when time to board I received the very last seat. Please relay to employees to do their job better..,

On this flight I felt the food offering was not as complete as on previous flights. The tomato salad was a bit off and there was nothing additional such a bread or butter. The breakfast was only one option, so you either ate what they had or ate nothing. The crew was efficient, but most seemed frustrated throughout the flight. The flight arrived early and was obstacle-free, so I’m overall quite happy, but the shine in the rest of the experience just wasn’t there.

The seats got pretty uncomfortable pretty fast. The armrests are bigger than on other planes, so I had less room in the actual seat. My butt hurt by the end of the flight. :/ comfort was the primary issue. The crew were fantastic!

I believe that a four-hour trip should have a meal. Delta had none.

Great flight with Delta! Boarding was quick and easy, the amenities were solid, and the plane was in great shape. The flight attendants had a fun, lively energy while staying professional. All in all, a smooth trip — even managed to catch up on some rest. Thanks, Delta!

I was uncomfortably cold on the plane. Other than that it was uneventful and therefore as enjoyable as a plane ride can be.

There was supposed to be a meal served, but there wasn’t and the major toilet was out of order

They made us board and then deboard due to mechanical issue which delayed the departure by almost 2 hours and we barely made our connecting flight. These quality checks should've been done before boarding not after.

Having to up charge for a seat assignment is not good. Delta can do better

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.

Great experience…left a bit behind schedule but made up fir that in the air and landed 10 minutes early 😁

The seat and leg room was not good. The food and beverage service was good.

For economy, it was very good. Staff was great, they even let some of us change seats for more leg room... Put an empty seat between us which was fantastic for a 12hr flight. Onboard entertainment was excellent, I think over 200 choices of movies/tv/etc The bad was the barely/nonfunctional wifi that cost either $16.99 or 1700 miles (full flight). It was atrocious... Definitely the worst of the last 3 long haul major airlines I was on the last few months.

Electric plugs didn't work. Entertainment system wasn't working

The design of the light switch on the arm rest is ridiculous.

The gate attendant let me walk right by her with a bag too big for the overhead compartment

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

I don’t understand the purpose of the orange “priority” tag on my bag. This tagged, my bag is last or near to the last bag to come down the carousel at IAH.

Food was ok, but not as good as I have had before on AA.

No issues. They did change our gate FOUR times in about 30 minutes which was mildly annoying but the flight was fine.

Great flight. No issues at all. I still think boarding could be more efficient but otherwise, a good experience.

Pretty good. The food was just mediocre, the boarding and crew were good.

The comfort of the seats was great, the crew eased my child’s anxieties and the fact that I had full cans of my beverage choice was great.

My flight got switched and my prepaid bag didnt transfer over properly so I paid to check ANOTHER BAG. I was placed in a middle seat and it was just miserable. At least it was a bulkhead row so I had legroom. The flight just never seem3d to end

4 hours late, including over +1 hour waiting in plane to take off. Baggage left behind too.

Sat on the ground in Cincinnati for 50 minutes before deplaning

While waiting to claim my checked luggage, I discovered the airline had lost it. After a long wait and inquiries, I discovered it was on another flight. Fortunately, the airline finally sent my luggage home.

Crew should be nicer and emphatic with customers. Same cookies as the past 20 years. Seat are ok and the plane was clean though it was delayed.

Everything you need to know for your flight to Caribbean

Information on your arrival and departure airports

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