$140 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 2/23. 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$461
Santo Domingo
Santo Domingo2 stops$419
Montego Bay
Montego Bay1 stop$524
Nassau
Nassau2 stops$499
Kingston
Kingston2 stops$829
Providenciales
Providenciales2 stops$788
Bridgetown
Bridgetown2 stops$882
George Town
George Town2 stops$516
Aguadilla
Aguadilla2 stops$585
Punta Cana
Punta Cana2 stops$461
Santo Domingo
Santo Domingo2 stops$419
Montego Bay
Montego Bay1 stop$524
Nassau
Nassau2 stops$499
Kingston
Kingston2 stops$829
Providenciales
Providenciales2 stops$788
Bridgetown
Bridgetown2 stops$882
George Town
George Town2 stops$516
Aguadilla
Aguadilla2 stops$585

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

Mon, May 4 - Thu, May 7
American Airlines Logo
1:39 pm - 10:53 am
COS
-
SJU
19h 14m
2 stops
American Airlines Logo
11:59 pm - 12:45 pm
SJU
-
COS
14h 46m
1 stop
$286American Airlines
Tue, Feb 17 - Tue, Feb 24
American Airlines Logo
1:59 pm - 10:00 am
COS
-
SJU
17h 01m
2 stops
American Airlines Logo
7:00 am - 4:00 pm
SJU
-
COS
12h 00m
2 stops
$369American Airlines
Mon, May 4 - Thu, May 7
Southwest Logo
8:00 pm - 10:35 am
COS
-
SJU
12h 35m
2 stops
Southwest Logo
6:50 am - 9:45 pm
SJU
-
COS
16h 55m
2 stops
$374Southwest
Sun, Mar 8 - Sun, Mar 15
American Airlines Logo
1:39 pm - 9:00 am
COS
-
SJU
17h 21m
2 stops
American Airlines Logo
1:30 am - 12:48 pm
SJU
-
COS
13h 18m
1 stop
$380American Airlines
Tue, May 12 - Wed, May 20
Southwest Logo
6:30 am - 9:05 pm
COS
-
SJU
12h 35m
2 stops
Southwest Logo
8:10 am - 8:15 pm
SJU
-
COS
14h 05m
2 stops
$396Southwest
Tue, May 26 - Tue, Jun 2
United Airlines Logo
7:30 am - 5:30 pm
COS
-
SJU
8h 00m
1 stop
United Airlines Logo
1:05 am - 10:41 am
SJU
-
COS
11h 36m
2 stops
$406United Airlines
Fri, Feb 13 - Fri, Feb 20
Multiple Airlines Logo
10:58 am - 2:25 am
COS
-
SJU
12h 27m
1 stop
Multiple Airlines Logo
7:44 pm - 7:40 am
SJU
-
COS
38h 56m
2 stops
$412Multiple Airlines
Tue, Feb 17 - Tue, Feb 24
Delta Logo
1:22 pm - 11:58 pm
COS
-
SJU
7h 36m
1 stop
Delta Logo
6:15 am - 12:25 pm
SJU
-
COS
9h 10m
1 stop
$424Delta
Fri, Jan 30 - Sat, Feb 7
United Airlines Logo
1:25 pm - 1:50 pm
COS
-
SXM
21h 25m
2 stops
United Airlines Logo
5:00 pm - 10:57 am
SXM
-
COS
20h 57m
2 stops
$444United Airlines
Mon, Feb 23 - Wed, Feb 25
Delta Logo
12:00 pm - 11:10 am
COS
-
MBJ
21h 10m
2 stops
Delta Logo
2:00 pm - 12:25 pm
MBJ
-
COS
24h 25m
2 stops
$593Delta
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 $704 and $641 respectively.

Good to know

Low seasonSeptember
Cheapest flight$140
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.

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 4261 reviews
8.6Crew
7.5Entertainment
8.0Comfort
7.0Food
8.1Boarding
Airline reviews

The seats were comfortable, and the boarding process was pretty smooth.

10.0 ExcellentJohn, Jan 2026
BWI - MDW
Read more Southwest reviews

The seats were comfortable, and the boarding process was pretty smooth.

3 hour delay. Had to change plans and was still delayed.

The staff was very friendly, professional, and courteous. The overall flight was a great experience.

The crew canceled the complementary snack and drink in anticipation of turbulence that never materialized. I was counting on the drink (water) to take the the doses of medication - prescribed for my heart condition - that were due during the flight. Since no snack or meal was served on this flight, I cannot rate the food quality. Otherwise, this flight was excellent.

Departure was delayed more than 1/2 hour while we waited for luggage (only) transfer from another flight/plane. Once approved for takeoff, the flight was excellent.

We got exit row seats both flights. Everything was running on time

The flight crew was extremely rude and especially not helpful when our flight was delayed.

Pretty seamless, just a tad bit late in taking off and landing.

Flight was fine other than there was a gate change that I was not notified of. By chance I happened to check my phone and saw the change, otherwise, we would have missed our connecting flight.

Haven’t flown on SW in years. Flight was on time departing and arriving. Served vegan butter onion flavored pretzels which were bad. Coke served was in a tiny paper cup. Crew was not engaging. Felt like they were going through the motions. Old plane, tight seats and no leg room.

No in flight service, no explanation - FC got service, C+ did not, unsure about Economy. No turbulence to speak of, so I guess another way to cut cost, or promote health and well being of Delta employees? Also, boarding in MEM combined zones, and with overhead space already full on both flights after Zone 2/ Diamond, presents a huge challenge to find a space for a bag. Delta, other than point A to B, is no longer reasonable to fly - very poor experiences, not even taking into account the chastising at the gate and rude crews, across the board.

It would have been better if the flight wasn't delayed by 2.5 hours

Delta’s staff is unmatched. From the gate agents, to the pilots, to the flight attendants… all top of the industry.

Delta flight Delay for ,more that two hours i.e original flight was 6.30 PM and it starts at 8.45 PM, When we connect Delta team for meal vouchers as it is late arrival in designation,But we did not get it as per delta policy , which is not good for mid night arrival,

Inexperienced boarding crew allowed too many bags on to a full flight and delayed takeoff causing a missed connection and unplanned overnight stay. There was a hotel at the airport but Delta would not pay for it offering only to shuttle me to an area hotel. Never even offerred so much as an apology by anyone working for Delta.

Staff was great! Kind and cordial! Middle seat row 28 seat B has a hump in it. Trays were getting stuck when putting down and up. Good flight

Departure was delayed resulting in me missing my connection. Delta did not autimatically find me another flight.

The seats weren’t reclining even though it wasn’t as exit seat

It was good because we traveled without luggage, carry on only.

I usually get upgraded so my experience is usually amazing. I did not get upgraded this time - which was fine - but the wifi had issues, the monitors were going in & out, & (though not Delta's fault) one of the gentlemen next to me desperately needed a shower.

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.

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.

The seat cushions were very worn so they were extremely uncomfortable.

Delayed, no updates, had a rewards number but was not working

The seats from lax to DFW was so tight that I could not move my legs . No WiFi and had to pay . Not a good selection of entertainment

AA should improve their in air internet & entertainment options. Seems unreasonable to charge $20/hr and should have some form of free connections. The entertainment options are also pretty limited, movies are outdated and the series only show 3-5 episodes.

The professionals have excellent customer service, the seats don´t have enough space.

We were upgraded to First Class and it was a great flight

Amazing I love American. I’ll never fly anyone else if I can help it.

I love American. I’ll never fly anyone else if I can help it.

Flight delay and multiple gate changes including a change near boarding time to another terminal, which in DFW is a pain. Pre-boarding delay and also a further delay on the ground after boarding. About an hour and a half total delay.

On the plus side, crew was attentive, drinks were cold, and in-flight entertainment selection was better than some other airlines. On the negative aide, Plane was delayed almost an hour, either no announcements from the gate crew. Biscoff cookies are gross, appreciate airlines that give a choice. Also, crew had no personality or enthusiasm at all.

Everything you need to know for your flight to Caribbean

Information on your arrival and departure airports