$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 3/18. 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 Cana1 stop$462
Santo Domingo
Santo Domingo2 stops$398
Montego Bay
Montego Bay1 stop$450
Oranjestad
Oranjestad2 stops$686
Nassau
Nassau2 stops$510
Kingston
Kingston2 stops$808
Providenciales
Providenciales2 stops$1,039
Bridgetown
Bridgetown2 stops$596
George Town
George Town1 stop$500
Aguadilla
Aguadilla2 stops$355
Punta Cana
Punta Cana1 stop$462
Santo Domingo
Santo Domingo2 stops$398
Montego Bay
Montego Bay1 stop$450
Oranjestad
Oranjestad2 stops$686
Nassau
Nassau2 stops$510
Kingston
Kingston2 stops$808
Providenciales
Providenciales2 stops$1,039
Bridgetown
Bridgetown2 stops$596
George Town
George Town1 stop$500
Aguadilla
Aguadilla2 stops$355

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

Sun, May 3 - Wed, May 6
American Airlines Logo
5:11 pm - 2:35 pm
COS
-
SJU
19h 24m2 stops
American Airlines Logo
3:20 pm - 11:25 pm
SJU
-
COS
10h 05m1 stop
$348American Airlines
Sun, Jan 25 - Sun, Feb 8
American Airlines Logo
6:12 am - 10:26 pm
COS
-
SJU
13h 14m1 stop
American Airlines Logo
7:07 am - 2:12 pm
SJU
-
COS
10h 05m1 stop
$375American Airlines
Thu, Jan 8 - Mon, Jan 12
American Airlines Logo
3:17 pm - 10:48 am
COS
-
SJU
16h 31m2 stops
American Airlines Logo
5:51 pm - 9:51 am
SJU
-
COS
19h 00m2 stops
$383American Airlines
Mon, Mar 2 - Fri, Mar 6
American Airlines Logo
1:43 pm - 9:48 am
COS
-
SDQ
17h 05m2 stops
American Airlines Logo
6:43 pm - 12:50 pm
SDQ
-
COS
21h 07m2 stops
$398American Airlines
Sat, Jan 10 - Fri, Jan 23
United Airlines Logo
3:30 pm - 6:11 am
COS
-
SJU
11h 41m2 stops
United Airlines Logo
2:05 am - 12:22 pm
SJU
-
COS
13h 17m2 stops
$406United Airlines
Tue, May 26 - Mon, Jun 1
United Airlines Logo
1:50 pm - 5:30 am
COS
-
SJU
13h 40m2 stops
United Airlines Logo
1:05 am - 11:18 am
SJU
-
COS
12h 13m2 stops
$414United Airlines
Sat, Feb 21 - Thu, Feb 26
Southwest Logo
5:55 pm - 2:55 pm
COS
-
STT
18h 00m2 stops
Southwest Logo
3:45 pm - 10:40 am
STT
-
COS
21h 55m2 stops
$483Southwest
Tue, May 26 - Tue, Jun 2
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
$489Delta
Wed, Apr 22 - Mon, Apr 27
Delta Logo
6:20 am - 3:54 pm
COS
-
NAS
7h 34m1 stop
Delta Logo
3:03 pm - 8:19 pm
NAS
-
COS
7h 16m1 stop
$580Delta
Sun, Feb 22 - Thu, Feb 26
Air Canada Logo
1:40 pm - 12:25 pm
COS
-
GCM
20h 45m2 stops
Air Canada Logo
1:30 pm - 11:45 pm
GCM
-
COS
36h 15m2 stops
$1,105Air 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.

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.

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 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 4257 reviews
8.6Crew
8.0Comfort
8.1Boarding
7.5Entertainment
7.0Food
Airline reviews

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.

10.0 ExcellentAnonymous, Dec 2025
DAL - CHS
Read more Southwest reviews

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!

No delays and arrived to destination 30 min early. Staff was super friendly.

San Diego airport is brand new, spacious, airy and very smooth checkin at SW baggage drop.

Advertised fruit trays with cheese, but only snacks handed out!

The plant way delayed departing by 3 hours. It was an old airplane with broken seats and armrests. The bathroom made a hollering sound. A really crappy flight experience and travel day all around.

Flight delays both to Detroits and return flight . The flight to Detroit was associated with mechanical difficulty

I am extremely disappointed that delta internal pilot manuals now refer to the Gulf of Mexico as the “gulf of America”. You can bow down to the Orange turd on your own. I will never fly delta again

Wasn't a Delta issue I don't think, but seems there was a Delta flight at each of the 2 Dallas airports at the same exact time, both to Atlanta. I was evidently booked on the one at Love Airport, but the Carey transport shuttle took me to DFW instead and I ended up missing the flight by just a few minutes. Was able to book a Southwest flight from Love Airport, but was a big loss of time and an inconvenience.

Great. I had to modify a flight. That was easy and free. Thank You

I noticed that the planes seem to be outdated. There was no entertainment per se. Also, the waiting area did not have any working electrical outlets

None of the airplane features were available during the flight.

Original flight was cancelled and when i was rebooked by the airline, they couldn't seat me in the same type of seat as I had originally booked (went from window/aisle to middle/middle and one was a bulkhead seat, and other wasn't in the same class)

Lady Pilot was perfect in every way wheels up to wheels down communication, professionalism, excellent on time departure and on time arrival, excellent communication! Fantastic job with Superb attitude!!

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.

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

Great flight - friendly and attentive team! Seats in coach were comfy, but a little cramped - but that is the case with all airlines ;)

The boarding by groups is pointless. The first two groups worked fine, but almost Noone boarded in goups three thru five leaving the vast majority boarding when group six was called. It defeated the purpose of spreading out the crowd.

I don’t know who decides what food to serve on these flights but I would be so embarrassed if I served this to anyone and call it food…

For whatever reason, the flight was not catered -we were told it would be a 45 minute delay waiting for catering - so no food. There were opened candy and peanuts in the seatback pocket. Flight landed early in DFW but due to the assigned gate not being available, we sat on the ground for 30 minutes waiting for the gate to open - making the flight actually arrive at the gate late.

Not great. Booked Extra seats and got nothing extra at all. It’s basically a big budget airline.

The pilot greased the landing and the crew was fantastic.

I bought wifi and most of the flight could not even use it my apps would just spin. I couldn't even listen to music. super frustrating.

delayed due to weather. Could not communicate with family since the wifi was broken

Experience was good, however I had a delay due to weather happening and had to re purchase a seat on a new plane for a higher price (could be my own issue and misunderstanding) but other than that situation. First time flyer (by myself) was terrific!! The last from ORD to ALO didn't have wifi, but it was only 45 minutes so I'm sure that was part of the reason. Overall my experience was great! Next time I will remember to buy tickets with longer layovers. The delays really saved my overall anxiety. :)

Flight was delayed 17 hours due to aircraft issues. American did provide hotel, transportation and meals, 3 hours past boarding time, but it took us another hour to get the vouchers.

Everything you need to know for your flight to Caribbean

Information on your arrival and departure airports