$171 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 5/11. 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 Cana1 stop$573
Santo Domingo
Santo Domingo2 stops$655
Montego Bay
Montego Bay2 stops$397
Oranjestad
Oranjestad2 stops$556
Nassau
Nassau2 stops$512
Kingston
Kingston2 stops$956
Providenciales
Providenciales2 stops$522
Bridgetown
Bridgetown2 stops$1,075
George Town
George Town2 stops$600
Punta Cana
Punta Cana1 stop$573
Santo Domingo
Santo Domingo2 stops$655
Montego Bay
Montego Bay2 stops$397
Oranjestad
Oranjestad2 stops$556
Nassau
Nassau2 stops$512
Kingston
Kingston2 stops$956
Providenciales
Providenciales2 stops$522
Bridgetown
Bridgetown2 stops$1,075
George Town
George Town2 stops$600

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

Wed, Sep 16 - Wed, Sep 23
American Airlines Logo
3:51 pm - 2:45 pm
COS
-
SJU
20h 54m
2 stops
American Airlines Logo
6:30 am - 10:57 pm
SJU
-
COS
18h 27m
2 stops
$347American Airlines
Tue, May 5 - Wed, May 13
American Airlines Logo
5:13 pm - 4:15 pm
COS
-
STT
21h 02m
2 stops
American Airlines Logo
12:25 pm - 11:32 pm
STT
-
COS
13h 07m
2 stops
$368American Airlines
Sat, May 2 - Sat, May 9
American Airlines Logo
1:39 pm - 9:13 am
COS
-
SJU
17h 34m
2 stops
American Airlines Logo
5:45 am - 4:23 pm
SJU
-
COS
12h 38m
2 stops
$373American Airlines
Sat, May 2 - Sat, May 9
American Airlines Logo
1:39 pm - 10:53 am
COS
-
SJU
19h 14m
2 stops
American Airlines Logo
11:59 pm - 9:27 am
SJU
-
COS
11h 28m
1 stop
$374American Airlines
Tue, Aug 25 - Tue, Sep 8
Southwest Logo
10:45 am - 10:00 pm
COS
-
SJU
9h 15m
2 stops
Southwest Logo
8:20 am - 5:00 pm
SJU
-
COS
10h 40m
2 stops
$391Southwest
Fri, May 1 - Fri, May 8
United Airlines Logo
6:57 pm - 3:10 pm
COS
-
MBJ
19h 13m
2 stops
United Airlines Logo
2:40 pm - 8:47 am
MBJ
-
COS
19h 07m
2 stops
$397United Airlines
Tue, Aug 25 - Tue, Sep 8
American Airlines Logo
10:12 am - 11:40 pm
COS
-
SJU
11h 28m
2 stops
American Airlines Logo
3:42 pm - 10:57 pm
SJU
-
COS
9h 15m
1 stop
$399American Airlines
Fri, May 1 - Fri, May 8
United Airlines Logo
6:57 pm - 3:45 pm
COS
-
MBJ
19h 48m
1 stop
United Airlines Logo
4:12 pm - 8:47 am
MBJ
-
COS
17h 35m
2 stops
$402United Airlines
Sat, May 2 - Sat, May 9
Southwest Logo
5:25 pm - 12:05 pm
COS
-
NAS
16h 40m
2 stops
Southwest Logo
8:45 am - 8:45 pm
NAS
-
COS
14h 00m
2 stops
$512Southwest
Fri, Jun 26 - Mon, Jul 6
Delta Logo
2:25 pm - 12:39 pm
COS
-
SDQ
20h 14m
2 stops
Delta Logo
2:41 pm - 9:48 pm
SDQ
-
COS
9h 07m
1 stop
$1,367Delta
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.

Which airlines provide the cheapest flights from Colorado Springs to Caribbean?

The cheapest round-trip price for the route for each airline clicked by KAYAK users in the last 72 hours.

In the past 3 days, the cheapest round-trip tickets from Colorado Springs to Caribbean were found on American Airlines ($368) and United Airlines ($402).

Good to know

Low seasonSeptember
Cheapest flight$171
Best time to beat the crowds with an average 27% drop in price.
Most popular time to fly with an average 9% 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 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 4324 reviews
8.1Boarding
8.0Comfort
7.5Entertainment
7.0Food
8.6Crew
Airline reviews

Southwest was greaat! The most expensive but the least upsetting for those we were flying to see.

10.0 ExcellentMartie, Mar 2026
LGB - BNA
Read more Southwest reviews

Southwest was greaat! The most expensive but the least upsetting for those we were flying to see.

I flew twice this week on Southwest, was delayed over 2 hours both ways. From Pittsburgh to Chicago it was due to weather but the gate agents, pilot etc were great at updating everyone. Today from Midway to Pittsburgh the plane had come from an international location, kept getting delayed, no information was given until we were delayed for the third time. It was ridiculous, whoever scheduled that plane to fly to Pittsburgh after didn’t consider a lot of things.

Boarding was easy. The seats are small and fairly uncomfortable

I was supposed to be on a later flight. When I showed up at the gate, the woman working there was extremely helpful getting moved up to this earlier flight.

We had a 5 hour delay on the tarmac in Baltimore

Long layover between flights to Long Island from BWI - need better coordination between flights

I elected to pay for the upgrades and found very little difference

The new seating arrangement is so over priced for what you get.

The problem with the seat assignments is that there were a lot of rows in the front that were empty but my row at the back was full. Just not so pleasant.

No food or entertainment, just a quick 40 minute flight. A little bumpy due to Santa Ana winds but pilot has no control over that. Good flight and landing!

Entertainment is ok! Boarding and seat with zone is terrible. I paid for the seats but you didn’t give me what I paid for which is exit isles.

the crew cancel the morning service due to the weather. Then the flight got deverted to Nashville . we were on the ground for over two hours the only gave us water once... no food or any snacks.... the crew should have handled better and offered something to passengers.

My recent experience was excellent on Delta! I flew with Delta Comfort and I was really comfortable in my seat. I enjoyed the in-flight service. The flight attendants were so friendly and hospitable. I love the snack on the flight as well. This was my first time flying on Delta and I will definitely consider flying with them again.

My flight was cencaled due with the bad weather on Sunday the crew was poorly mistaken my luggage supposed depart with my flight instead I didn’t have my luggage for almost 3 days the website is poorly respond to my complain until I have someone to do it my connection smooth their not even respon or email me even the have my luggage

Delta needs to step its game up get a more reliable internet service. Internet service was non-existent for this flight.

Mechanical Delay of over an hour with multiple gate changes. Entertainment system down for rejuvenation.

This was a Latam operated flight. Seats seemed a bit narrow in business class. Older aircraft.

I had a flight cancel and had it rerouted. When the rerouted they put me at a window seat instead of an isle. It was hard sitting by the window because the couple with masks on were making out. I get motion sickness which is why I need to have the isle seat.

NEVER MADE THE FLIGHT BECAUSE DELTA SAID THEY CAN NOT

THEY FAILED ME AND I NEVER GOT ON THE FLIGHT BECAUSE IT WAS SO DELAYED! I ENDED UP HAVING TO PAY OUT OF POCKET FOR A HOTEL AND STAY IN NASHVILLE TO CATCH A FLIGHT FOR THE FOLLOWING DAY. DELTA IS POOR CUSTOMER SERVICE>

ticket agent lady wás very helpful , she arranged wheel chair for my elderly mother

Flight left on time and we arrived 25 minutes early! There was a gate available when we arrived so early on a busy Sunday afternoon! Flight attendants came around twice with the drinks cart.

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

Sitting on the runway after we land for almost two hours! Not sure if we should blame United or Just Dumpy Vance.

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.

Absolutely terrible. Would never fly American again. 2 deplaned incidents and delayed by close to 24 hours. $12 meal voucher for first class passengers was an insult to the injury. Pathetic.

Terrible planning. And even worse gate agents. Absolutely rude behavior.

Half of the TSA checkpoints at PHL are closed. Also, there is no standby for first class passengers. You can only standby for coach. Very dated policy and inconsistent with peers.

Flight was scheduled at 11:26am but they keep Delaying until midnight. They waited at airport restless.

Rough flight No beverage service due to turbulence Bottom Seat cushion was non existent

Great experience. Good dinner and service. FA's were very nice and attentive.

It was great. Smooth flight, comfortable, left on time and landed on time.

Perhaps this is an airport issue, but being in a takeoff queue for over an hour in the taxiing lane is unacceptable. We will definitely be seeking alternative avenues for air travel in the future.

We hoarded. Then we deplaned. Then we waited for 10 hours in the MSP airport due to a wheel misfunction. We understand safety but communication between crew and airport staff was horrible. When we did finally board, we were rushed on and because we were waiting for a “fresh” pilot and crew, we sat in a roasting plane with no A/C for an hour. My question is why was this flight not cancelled right away when they knew this would be a huge issue OR, why did AA not get a substitute plane, considering this was already a full flight? To me, this appears to be a complete breakdown in leadership and utter systems failure. The compensation for completely disrupting travel plans for hundreds, which we paid dearly for, was measly. While we appreciated the lodging for the night, $12 in meal vouchers isn’t going to sustain anyone for over 12 hours. “We apologize; our hands are tied” is no longer an acceptable explanation. We are so completely turned off by this experience and will definitely seek alternative avenues when we need to fly.

Mostly good. The WiFi wasn’t working so that was not great.

Everything you need to know for your flight to Caribbean

Information on your arrival and departure airports