$218 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 1/11. 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$445
Montego Bay
Montego Bay1 stop$503
Oranjestad
Oranjestad2 stops$1,196
Nassau
Nassau2 stops$580
Kingston
Kingston2 stops$708
Providenciales
Providenciales2 stops$657
Bridgetown
Bridgetown2 stops$736
George Town
George Town1 stop$600
Aguadilla
Aguadilla3 stops$265
Punta Cana
Punta Cana2 stops$466
Santo Domingo
Santo Domingo2 stops$445
Montego Bay
Montego Bay1 stop$503
Oranjestad
Oranjestad2 stops$1,196
Nassau
Nassau2 stops$580
Kingston
Kingston2 stops$708
Providenciales
Providenciales2 stops$657
Bridgetown
Bridgetown2 stops$736
George Town
George Town1 stop$600
Aguadilla
Aguadilla3 stops$265

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

Sat, Jan 24 - Sun, Feb 1
American Airlines Logo
6:02 am - 11:59 pmCOS-SJU
14h 57m2 stops
American Airlines Logo
6:00 am - 8:57 pmSJU-COS
17h 57m2 stops
$265American Airlines
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Tue, Mar 10 - Wed, Mar 11
American Airlines Logo
12:45 pm - 8:36 amCOS-SJU
17h 51m2 stops
American Airlines Logo
3:45 pm - 9:06 amSJU-COS
19h 21m2 stops
$337American Airlines
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Thu, Dec 4 - Thu, Dec 11
Multiple Airlines Logo
3:26 pm - 11:25 pmCOS-SJU
52h 59m2 stops
Multiple Airlines Logo
7:00 am - 9:00 amSJU-COS
29h 00m1 stop
$375Multiple Airlines
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Tue, Mar 10 - Wed, Mar 11
United Airlines Logo
7:00 am - 9:22 pmCOS-SJU
12h 22m2 stops
United Airlines Logo
1:25 pm - 10:02 pmSJU-COS
10h 37m1 stop
$474United Airlines
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Wed, Feb 18 - Tue, Feb 24
United Airlines Logo
6:55 pm - 11:50 amCOS-PUJ
13h 55m2 stops
United Airlines Logo
2:05 pm - 9:04 pmPUJ-COS
9h 59m1 stop
$500United Airlines
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Sun, Dec 7 - Thu, Dec 11
Delta Logo
6:00 pm - 12:30 pmCOS-MBJ
16h 30m2 stops
Delta Logo
1:55 pm - 12:36 pmMBJ-COS
24h 41m2 stops
$508Delta
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Thu, Feb 12 - Mon, Feb 16
Southwest Logo
11:20 am - 1:05 amCOS-SJU
10h 45m2 stops
Southwest Logo
3:15 pm - 11:20 pmSJU-COS
11h 05m2 stops
$555Southwest
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Fri, Apr 24 - Wed, Apr 29
Delta Logo
6:00 am - 3:54 pmCOS-NAS
7h 54m1 stop
Delta Logo
3:03 pm - 9:22 pmNAS-COS
8h 19m1 stop
$580Delta
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Fri, Apr 24 - Wed, Apr 29
Southwest Logo
6:45 am - 6:30 pmCOS-NAS
9h 45m2 stops
Southwest Logo
8:45 am - 8:15 pmNAS-COS
13h 30m2 stops
$584Southwest
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Fri, Dec 5 - Sat, Dec 13
Multiple Airlines Logo
5:48 pm - 11:51 amCOS-SDQ
15h 03m3 stops
Multiple Airlines Logo
12:20 pm - 1:08 pmSDQ-COS
27h 48m3 stops
$1,402Multiple 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 March and December, when the average cost of round-trip tickets is $735 and $670 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$218
Best time to beat the crowds with an average 27% drop in price.
Most popular time to fly and prices are also 8% 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 4241 reviews
7.5Entertainment
8.1Boarding
8.6Crew
7.0Food
8.0Comfort
Airline reviews

Plane crashed into a bus or some other vehicle on the ground while pulling out of the gate. No injuries, but wing tip was damaged and returned to gate for “maintenance issues” and we departed 5 hours later because the plane went out of service and new plane was flown in from a nearby airport, Midway.

2.0 MediocreAnonymous, Nov 2025ORD - LAS
Read more Southwest reviews

Plane crashed into a bus or some other vehicle on the ground while pulling out of the gate. No injuries, but wing tip was damaged and returned to gate for “maintenance issues” and we departed 5 hours later because the plane went out of service and new plane was flown in from a nearby airport, Midway.

Ever since Southwest starting charging for bags, passengers don't want to pay to check their bags, so the gate agents have to beg people to check their roller bags now because there's "not enough space". This was a terrible business move by Southwest.

Full cans of soda would be nice. A choice between two snacks would be appreciated.

Tried watching free movie and it kept freezing so I couldn’t finish.

All was good. I just had a hard time getting connected to the WiFi/internet during the flight

Sacrament staff are always polite and helpful. Airport is easy to maneuver and boarding is straightforward.

Great flight. Outstanding Service. Southwest was able to put us on a direct flight to Denver when the connection could have been affected by a later arrival to Baltimore. The direct flight was less expensive that the flight with the connection in Baltimore.

Delays delays delays. Late taking off, late landing, wait for a gate, etc.

Boarded on time but once we were ready for take off, the crew determined that, although every seat was taken, somehow someone was on the wrong flight. Delay, delay delay, announcements and ended up with one person checking EVERY ID against their passenger Manifest only to figure out it was a "clerical error." We departed 54 minutes late causing me to run in the St. Louis Airport to make my connection and lose the priority boarding spot I had paid for. Unnecessary delay.

I was re-booked onto another flight because my original flight was delayed and I would have missed my connector. I ended up in the “C” group after paying extra to be in the “A “ group on the original flight. At least if you’re going to re-book people, re-book them into the same group.

I truly love flying with Delta. They have always treated me with the upmost respect

Our flight attendant in FIRST CLASS was one of the worst I’ve ever had. She was not at all pleasant, nor particularly good at her service.

Everything went well and was good. Nothing exceptional, but no complaints either. Cheap seats are pretty comfortable.

Staff were friendly and happy. Delta could make sure passengers that don't have the app know of changes. Without Kayak I would not have known about the change of gate or the delay. Kayak was faster to notify me.

They ended up paying for the bag twice, but the counter wouldn't take my baggage receipt. Left it to me to resolve. Not sure how to resolve the issue.

The customer service before board was very rude and when I expressed my concerns about making the connecting flight she laughed and told me I bought the wrong ticket. I explained once it showed the flight was delayed it no longer let me change seats or anything. I was trying to upgrade to make sure I would get to the next gate on time.

Non stop on long haul is the way to go. Great experience

The aircraft interior is old and tired on this aircraft. The entertainment system never worked despite the crews attempt to reset the system.

The flight used a B767 with a very old interior from before 2014. The entertainment system did not work at all during the flight despite attempts to reset the system. It was like they flew this route just to be competitive.

Old plane and old configuration/seats but still comfortable for a morning flight

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 😁

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.

We loved the steward on the plane. He made the night enjoyable

I enjoyed the extra leg room compared to other airlines. The first stewards made my daughter’s birthday special by giving her an extra snack. Then the last one coming home from Chicago to Appleton made our night really enjoyable Thanks for making our trip enjoyable

The flight was smooth, the pilot kept us informed about delays and we arrived more of less on time

Flight delay was communicated before leaving for airport which caused it to be a non-event. Great flight and crew!

Did not get any refreshments. Crew was very nice but limited. Small seats

Wish some foods provided rather than just biscuit/cookie for flight more than 2 hours

Wish a flight with more than 2 hours with some snack rather than just cookie/biscuit.

The flight attendant, a black woman with curly hair who sat near Row 21, was wonderful and kind.

It was good..clean, comfy seat. Friendly warm welcoming crew. Was able to check my cabin luggage at the gate which I was able to pickup in a decent time from baggage claim. The app gave all updates from delays to baggage claim info. Overall smooth flight.

Flight was delayed leaving Dallas. Arrived about 2 hours later than scheduled.

Everything you need to know for your flight to Caribbean

Information on your arrival and departure airports