$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 5/12. 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$491
Santo Domingo
Santo Domingo2 stops$629
Montego Bay
Montego Bay2 stops$467
Oranjestad
Oranjestad2 stops$632
Nassau
Nassau2 stops$502
Kingston
Kingston2 stops$705
Providenciales
Providenciales2 stops$581
Bridgetown
Bridgetown2 stops$1,005
George Town
George Town2 stops$497
Aguadilla
Aguadilla2 stops$418
Punta Cana
Punta Cana2 stops$491
Santo Domingo
Santo Domingo2 stops$629
Montego Bay
Montego Bay2 stops$467
Oranjestad
Oranjestad2 stops$632
Nassau
Nassau2 stops$502
Kingston
Kingston2 stops$705
Providenciales
Providenciales2 stops$581
Bridgetown
Bridgetown2 stops$1,005
George Town
George Town2 stops$497
Aguadilla
Aguadilla2 stops$418

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, May 2 - Fri, May 8
United Airlines Logo
6:00 am - 8:34 pm
COS
-
SJU
12h 34m
2 stops
United Airlines Logo
1:00 am - 12:26 pm
SJU
-
COS
13h 26m
2 stops
$356United Airlines
Sat, Sep 26 - Wed, Oct 21
American Airlines Logo
5:13 pm - 2:45 pm
COS
-
SJU
19h 32m
2 stops
American Airlines Logo
8:30 am - 10:57 pm
SJU
-
COS
16h 27m
2 stops
$382American Airlines
Sat, Sep 26 - Wed, Oct 21
American Airlines Logo
3:51 pm - 12:40 pm
COS
-
SJU
18h 49m
2 stops
American Airlines Logo
8:30 am - 10:57 pm
SJU
-
COS
16h 27m
2 stops
$384American Airlines
Sat, May 2 - Sat, May 9
Delta Logo
6:15 am - 4:23 pm
COS
-
SJU
8h 08m
1 stop
Delta Logo
6:15 am - 12:48 pm
SJU
-
COS
8h 33m
1 stop
$401Delta
Fri, May 1 - Wed, May 13
United Airlines Logo
6:57 pm - 12:20 pm
COS
-
STT
15h 23m
2 stops
United Airlines Logo
1:22 pm - 11:59 pm
STT
-
COS
12h 37m
2 stops
$419United Airlines
Sat, Sep 26 - Wed, Oct 21
American Airlines Logo
5:13 pm - 2:45 pm
COS
-
SJU
19h 32m
2 stops
American Airlines Logo
5:24 am - 2:45 pm
SJU
-
COS
11h 21m
1 stop
$420American Airlines
Sat, Sep 26 - Wed, Oct 21
American Airlines Logo
8:00 am - 11:59 pm
COS
-
SJU
13h 59m
2 stops
American Airlines Logo
5:24 am - 2:45 pm
SJU
-
COS
11h 21m
1 stop
$422American Airlines
Sat, Sep 26 - Wed, Oct 21
Delta Logo
6:00 am - 4:31 pm
COS
-
SJU
8h 31m
1 stop
Delta Logo
2:31 pm - 9:21 pm
SJU
-
COS
8h 50m
1 stop
$439Delta
Fri, Jul 24 - Sun, Aug 2
Southwest Logo
9:35 am - 12:25 am
COS
-
SJU
12h 50m
1 stop
Southwest Logo
5:45 am - 4:45 pm
SJU
-
COS
13h 00m
1 stop
$449Southwest
Wed, May 13 - Fri, May 22
Southwest Logo
4:45 pm - 1:15 pm
COS
-
NAS
18h 30m
2 stops
Southwest Logo
8:45 am - 9:45 pm
NAS
-
COS
15h 00m
2 stops
$580Southwest
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 January, when tickets cost $422 (return) on average. On the other hand, the most expensive months are March and August, when the average cost of round-trip tickets is $736 and $641 respectively.

Good to know

Low seasonNovember
Cheapest flight$133
Best time to beat the crowds with an average 5% drop in price.
Most popular time to fly with an average 18% 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 4331 reviews
8.1Boarding
7.5Entertainment
7.0Food
8.6Crew
8.0Comfort
Airline reviews

The new boarding process was easy and straightforward. Very pleasant.

10.0 ExcellentAnonymous, Apr 2026
LAS - OKC
Read more Southwest reviews

The new boarding process was easy and straightforward. Very pleasant.

The flight was okay. The pilots did an amazing job and kept us updated on the flight. The flight attendants were okay. They found time to be chatty with each other rather than focus on the guests. One of the attendants was a little less warm when asking about my bag I had on my lap that I was using during latter part of the mid- flight. Mind you, it was not the departure descent. I’m respectful to each and every attendant, it was the tone in her voice reminding me to place my carryon bag on the floor. I hope to have a better experience next time.

The entire travel day was a disaster from beginning to end. Woke up at two in the morning to make it to San Juan airport in time for a 5:30 am flight to Milwaukee which connected in Baltimore. Massive delays lead to me missing original connection out of Baltimore. Sixteen hours of delays/rebooking/layover time later, arrived in Milwaukee to find that only one of two checked bags made it there (despite the fact that Southwest brought another 737 jet to San Juan to fly us out to our original Baltimore connection—-not squeezed into another booked flight). The flight from Baltimore to Milwaukee was barely half full, so there was no logical reason to ship my bags out of Baltimore on a different flight to Chicago to then ship to Milwaukee. Southwest decided that my bags should not have been on the same connecting flight I WAS ON to Milwaukee, and then proceeded to accidentally leave my larger bag with the important items in Chicago. Terrible logic and support all around. Extremely angered and disappointed with SW. What a clownish operation your company has become!

It was as expected and I was grateful for the wheel chair help and ease of use.

One of the best airlines for fast boarding, on time arrivals, and top notch service!

The new seat assignment thing is wierd. If you don’t pay for a seat they always assign you a middle seat regardless of how many people are on the flight. Idk… the new company that bought Southwest is trying to make it more profitable, but I’m just not seeing it. The flight attendants aren’t having as much fun anymore. It just feels like the airline is slowly dying. IMO. We shall see if Southwest is the next Toy’s R Us.

Terrible. Even though there’s assigned seating now, they are still the slowest boarding airline of anyone.

The Air hostess were very rude on my flight from Houston to Austin . Their regular communication itself felt a they are shouting at people.

Communication about the delayed flight was poor. We were told to move gates three times but that was bad information. We went from gate 128 to gate 126 and then to gate 123 and back to gate 126. Communication about the delay was bad. Ended up being 1 1/2 hour late getting home.

Plane was late. Zero service for 2+ hour flight and it was not that bumpy.

The tray table was broken and the food was terrible.

The gentleman at the gate I think his name is RIE was exceptional

While they turned off most cabin lights to allow people to sleep, I was bothered by how bright the side lights still were. It was still quite bright for me in a window seat, when I wish I could have slept!

One of the flight attendants was a little cranky. I appreciated the free wifi and plug to charge my laptop

No entertainment. Plane was so small had to pink tag a carry on ive used for 20 years easily on board. The fact the flight got in at midnight, had to wait for crew in fort wayne to allow the plane to approach the gate, THEN had to wait for bag on jet bridge made experience irritating at best.

Crew was great. Near on time departure and early arrival. Snacks are always meh. Not a fan of the "pay for everything including miles " proposal unless base flight rate going to be 100 bucks.

Would have been better if there was a nonstop flight from Tampa to Norfolk or Tampa to New Port News.

Overall Good! The weather delayed our takeoff from Atlanta and our arrival in Miami! If Mother Nature can mess up a flight she will do it every time!

The flight was smooth, the crew was great but the plane was quite old

Everything was great until I lost my water bottle and they can’t seem to locate it. I know I left it on the plane though.

Every staff member was professional, friendly and courteous. The pizza twist was ok. It was warm but too much dough.

one staffer was frustrated (it happen); the flight was late and the pilot mentioned they'll make amend but the snacks were the same, other than that the aircraft was clean and everything went smooth, no complaints

Wonderful in-seat entertainment with seatback screens and huge selection of quality movies. The ability to bluetooth connect headphones was amazing.

No seat back entertainment. And app had a hard time getting entertainment loaded.

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.

Friendly crew is the only nice thing. Seats uncomfortable. Food and snacks horrible. Movies were the same as the first 10 hour flight two weeks before

When I booked my flight a month ago - I selected a seat. That seat was NOT the one I ended up with when I checked into my flight the day before. This is the second time this has occurred. So, I checked my next flight on Wednesday and Thursday and no seat was assigned. Poor, very poor customer service.

The staff and service on American Airlines were truly outstanding. I had requested wheelchair assistance for my mother due to her knee issues, and the team went above and beyond every step of the way—from boarding in Boston to our arrival in Chicago. Their care, professionalism, and attentiveness made the entire experience smooth and stress-free. I’m very grateful for the support they provided.

Incredibly delayed. First delay was due to plane coming in being late. Resulted in 30 minute delay. Boarded and then had multiple mechanical issues. Was on plane for an hour until they told people they could get off if they wanted but couldn't come back. Then gate agent rushed in and said they had lost control of who went off and we would all have to deplane and then get back on. They said flight had not been cancelled. Then while sitting waiting to board again they announced it would take two hours to get new plane and to wait at new gate. New plane arrived, reboarded only to find out that pilots had timed out. Waited for new pilots. In that time one of the flight attendants timed out. Never received food or water while waiting. Was confusing mess as to what was happening. Even flight attendants and gate agents were getting frustrated. Almost 6 hours delayed. Called American to received flight credit but can't get anywhere as Kayak reservation and don't have a ticket number. Reached out to Kayak but never heard back.

American flight was diverted and delayed but app didn’t show that information so I wasn’t able to change my connection until the last min.

Wifi was spotty. Tray table was very dirty when I sat down.

Very disappointing. Flight was delayed by 1.5 hours and food options are very underwhelming even for first class seats (same food given to economy seats)

Was not able to do a online check-in because the American Airlines system doesn't store our visa or other passport information, allowing us to have a trouble-free check-in. We were forced to have to check-in at the counter which Changes are upgrade status given that we were not able to check in much earlier.

The plane was very creaky and lots of ringing. Plane was dirty and dingy. I couldn't hear the captain's announcements from the flight deck. Not sure if it was the captain or the audio equipment, but good thing there wasn't an emergency where we needed clear instructions. The overhead compartments were clearly full, but the flight crew allowed people to stand in the back with their carry on luggage. Then after everyone boarded, they had to go to the front to gate check their luggage because there was no room for their bags and then they returned to their seats...such a waste of time when clearly the overhead compartments were full when they originally boarded.

The new planes (American Eagle) are beautiful and especially comfortable. The flight attendants are consistently professional and courteous. And, while it may seem inconsequential, the new liquid tube of coffee creamer—in contrast to the powdered coffee creamer—makes all the difference in a cup of coffee.

Everything you need to know for your flight to Caribbean

Information on your arrival and departure airports