$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 11/9. 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$462
Santo Domingo
Santo Domingo2 stops$518
Montego Bay
Montego Bay1 stop$508
Oranjestad
Oranjestad2 stops$666
Nassau
Nassau1 stop$665
Kingston
Kingston2 stops$696
Providenciales
Providenciales1 stop$1,424
Bridgetown
Bridgetown2 stops$718
George Town
George Town1 stop$600
Aguadilla
Aguadilla2 stops$885
Punta Cana
Punta Cana2 stops$462
Santo Domingo
Santo Domingo2 stops$518
Montego Bay
Montego Bay1 stop$508
Oranjestad
Oranjestad2 stops$666
Nassau
Nassau1 stop$665
Kingston
Kingston2 stops$696
Providenciales
Providenciales1 stop$1,424
Bridgetown
Bridgetown2 stops$718
George Town
George Town1 stop$600
Aguadilla
Aguadilla2 stops$885

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, Nov 11 - Thu, Nov 13
United Airlines Logo
10:34 am - 12:36 amCOS-SJU
11h 02m2 stops
United Airlines Logo
2:25 pm - 9:59 pmSJU-COS
10h 34m1 stop
$265United Airlines
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Tue, Nov 11 - Tue, Nov 18
United Airlines Logo
6:00 am - 9:26 pmCOS-SJU
12h 26m2 stops
United Airlines Logo
2:25 pm - 9:07 pmSJU-COS
9h 42m1 stop
$304United Airlines
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Tue, Mar 10 - Wed, Mar 11
American Airlines Logo
8:30 am - 8:36 amCOS-SJU
22h 06m2 stops
American Airlines Logo
3:45 pm - 11:30 amSJU-COS
21h 45m2 stops
$337American Airlines
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Tue, Nov 11 - Tue, Nov 18
American Airlines Logo
12:45 pm - 10:17 amCOS-SJU
18h 32m2 stops
American Airlines Logo
6:00 am - 8:27 pmSJU-COS
17h 27m2 stops
$350American Airlines
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Tue, Nov 11 - Mon, Nov 17
United Airlines Logo
10:34 am - 12:36 amCOS-SJU
11h 02m2 stops
United Airlines Logo
2:05 am - 10:53 amSJU-COS
11h 48m2 stops
$355United Airlines
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Wed, Oct 29 - Sat, Nov 1
Delta Logo
5:49 pm - 11:56 amCOS-SJU
16h 07m2 stops
Delta Logo
7:15 am - 6:11 pmSJU-COS
12h 56m1 stop
$559Delta
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Tue, Mar 31 - Thu, Apr 2
Delta Logo
12:25 pm - 2:20 pmCOS-BGI
23h 55m2 stops
Delta Logo
3:30 pm - 11:44 amBGI-COS
22h 14m2 stops
$718Delta
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Mon, Dec 22 - Sun, Dec 28
Multiple Airlines Logo
9:39 am - 12:37 amCOS-SJU
35h 58m2 stops
Multiple Airlines Logo
11:02 am - 9:20 amSJU-COS
25h 18m1 stop
$770Multiple Airlines
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Mon, Dec 22 - Sun, Dec 28
Multiple Airlines Logo
9:39 am - 12:57 amCOS-SJU
12h 18m1 stop
Multiple Airlines Logo
11:02 am - 9:20 amSJU-COS
25h 18m1 stop
$779Multiple Airlines
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Sat, Mar 21 - Sat, Mar 28
Southwest Logo
7:55 pm - 1:10 pmCOS-NAS
15h 15m2 stops
Southwest Logo
8:35 am - 4:35 pmNAS-COS
10h 00m2 stops
$887Southwest
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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 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.

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 1 week before departure. For the absolute cheapest price, our data suggests you should book 12 weeks before departure.

Good to know

Low seasonSeptember
Cheapest flight$133
Best time to beat the crowds with an average 28% 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.

  • 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 4238 reviews
7.5Entertainment
7.0Food
8.0Comfort
8.6Crew
8.1Boarding
Airline reviews

Flight was delayed due to plane not passing inspection And one of the crew had to time out and we had to wait for another one A 3 hour delay

4.0 OkayAnnette, Oct 2025LGA - MCI
Read more Southwest reviews

Flight was delayed due to plane not passing inspection And one of the crew had to time out and we had to wait for another one A 3 hour delay

mandatory demand customer to check their carry on because not enough people check bags.

Connecting flight is on time and boarding was a breeze!

Excellent. Would encourage Southwest to keep current boarding procedures with free style seating. Makes for a fantastic experience

As always, the entire Southwest experience was perfect. Purchasing the tickets on the Southwest web site was effortless, departure and arrival gates were spotless and comfortable, plane was clean and comfortable, crew was excellent and flight was on time. Wheelchair service in Las Vegas at departure was somewhat chaotic and disjointed, but I am not sure if that was Southwest problem, airport problem or combination.

I wish they had movie screens in the headrests. The seats are much improved, more legroom and recently renovated. Bathroom was clean. Staff was outstanding!!

As always, the entire Southwest experience was wonderful, from online booking to flight to baggage retrieval. Very grateful.

The weather could have been better. There was a 40 minute ATC delay in SFO because of marine fog and a micro cell storm delayed landing and take-off at Nashville. The gate was changed 5 minutes from boarding from gate B3 to gate C23 at Nashville airport.

After being assaulted by a flight attendant I was then brushed off as oh well because he long braids didn’t mean to whip me in the eye. I have filed complaints and will see. But like any other issue I’ve had with kayak involved it’s been trash. Last time I’ll be using your app

AC sub par. WiFi not working correctly. Ac sucked. Seats very narrow.

On time flight. Seat comfort could be better in the Comfort section.

My issue was with TSA agents for delta airlines. My luggage got flagged. The agent was going thru another persons first. He took 20 min to go thru hers. I asked them to bring mine closer so I could sit down . They said you can go sit it will be fine. I said I am supposed to keep my eyes on my bags at all times. The agent was meticulously unwrapping 2 gifts that the lady had and then tried to re warp it. He was trying to be kind i get it but 20 min for me to stand watching him do that was ridiculous. It was 6 am and there were a ton of travelers. Mine was flagged for some air packed tea that I bought in Turkey. My previous delta flight and 2 others before didn’t flag it. Consistency would be nice. Also on the flight the window shades were down for take off and landing - I thought that was very odd I thought they had to remain open for take off and landing.

The flight was an hour and a half late departing which was inconvenient

Delay in SLC jammed us up in Chicago. Got caught up in rush hour traffic

The crew took good care of us. The flight from ATL to SFO is a longer one, and there were multiple beverage offerings. I like the 757's that Delta uses. Good airplane that is comfortable. I do wish Delta would separate Priority boarding from the better seats. I would gladly take a smaller seat in an open row than be jammed into Comfort just to get priority boarding, just to make sure I don't have to check a bag.

The flight was great. The gate location was way to far away!!!

The flight attendant in first class was beyond rude and didn't care at all about her job. AND the gate agent was even worse than the flight attendant for rudeness. She was awful.

Gate agent rushed to fill hot jetway with crowd so it took over 12 minutes to go from gate to plane. Just like a discount airline Pooly prepared cabin and third time that claim of rough air prevented any cabin service. Friends on a Southwest flight at similar time had service.

Cramped seating for me. Luckily it wasn’t a long flight

Lounge in Lagos is terrible, food on board from Lagos to Atlanta was horrible. Only bright spot the cabin crew were awesome.

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.

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.

Mostly good. Flight was crowded but Airline personnel were very friendly & accommodating. It would be good to have savory snacks rather than just sweet Biscoff cookies.

It was a typical flight. We had a delay which seems to be the normality now. And we had no in flight service due to conditions.

Flight attendants on this flight were very attentive and friendly

After we landed we sat on the tarmac for 1.5 hours waiting to get to our gate. Ridiculous.

Food should be better quality. Video screens have poor resolution and the library of movies is poor. The other airlines are much better.

the trip to madrid was uncomfortable with my legs touching the seat in front of me

The plane was late, when we did board the plane was as cold as a freezer. I was freezing the entire flight, no blankets. Lost miserable flight I’ve ever had.

My flight was delayed for 17hs because the pilot forgot his passport!!! What a joke. AA used to be a great airline, now I have to think twice before flying with them again.

Terrible. Flight delayed for more than 8 hours with only a $12 meal voucher provided for the inconvenience. The airplane did not have breaks on arrival yet they still made us go through the motions and board on time knowing we could not take off then sit for 40+ minutes before having to get of the time. A complete waste of my time. I cannot believe they can stay business with these shenanigans. I’ll avoid this company like the plague moving forward as the lack of accountability is disgraceful.

This was the best 2 flights I have had with American out of SGF. Great crew both flights.

Everything you need to know for your flight to Caribbean

Information on your arrival and departure airports

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