$168 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 5/4. 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$577
Santo Domingo
Santo Domingo2 stops$519
Oranjestad
Oranjestad2 stops$612
Nassau
Nassau2 stops$536
Providenciales
Providenciales2 stops$888
Bridgetown
Bridgetown2 stops$1,042
George Town
George Town2 stops$569
Aguadilla
Aguadilla2 stops$747
Punta Cana
Punta Cana2 stops$577
Santo Domingo
Santo Domingo2 stops$519
Oranjestad
Oranjestad2 stops$612
Nassau
Nassau2 stops$536
Providenciales
Providenciales2 stops$888
Bridgetown
Bridgetown2 stops$1,042
George Town
George Town2 stops$569
Aguadilla
Aguadilla2 stops$747

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

mar., may. 5 - mar., may. 5
United Airlines Logo
6:00 am - 8:38 pm
COS
-
SJU
12h 38m
2 stops
United Airlines Logo
1:00 am - 10:47 am
SJU
-
COS
11h 47m
2 stops
$331United Airlines
sáb., sep. 26 - mié., oct. 21
United Airlines Logo
7:30 am - 5:30 pm
COS
-
SJU
8h 00m
1 stop
United Airlines Logo
2:55 pm - 11:59 pm
SJU
-
COS
11h 04m
2 stops
$336United Airlines
lun., abr. 20 - jue., may. 7
American Airlines Logo
5:41 am - 9:24 pm
COS
-
SJU
13h 43m
2 stops
American Airlines Logo
11:59 pm - 12:49 pm
SJU
-
COS
14h 50m
1 stop
$342American Airlines
dom., may. 10 - vie., may. 15
American Airlines Logo
1:39 pm - 11:35 am
COS
-
STT
19h 56m
2 stops
American Airlines Logo
5:05 pm - 12:49 pm
STT
-
COS
21h 44m
2 stops
$368American Airlines
sáb., sep. 19 - mié., oct. 14
American Airlines Logo
3:51 pm - 2:45 pm
COS
-
SJU
20h 54m
2 stops
American Airlines Logo
8:30 am - 10:57 pm
SJU
-
COS
16h 27m
2 stops
$374American Airlines
mar., may. 5 - mar., may. 5
United Airlines Logo
7:32 am - 8:38 pm
COS
-
SJU
11h 06m
1 stop
United Airlines Logo
1:00 am - 10:47 am
SJU
-
COS
11h 47m
2 stops
$406United Airlines
sáb., may. 2 - sáb., may. 9
Delta Logo
6:15 am - 8:24 pm
COS
-
SJU
12h 09m
1 stop
Delta Logo
2:48 pm - 9:27 pm
SJU
-
COS
8h 39m
1 stop
$409Delta
sáb., may. 2 - sáb., may. 9
Delta Logo
6:15 am - 8:24 pm
COS
-
SJU
12h 09m
1 stop
Delta Logo
6:15 am - 12:48 pm
SJU
-
COS
8h 33m
1 stop
$439Delta
lun., jul. 27 - vie., jul. 31
Southwest Logo
5:10 am - 6:30 pm
COS
-
NAS
11h 20m
2 stops
Southwest Logo
2:10 pm - 1:20 am
NAS
-
COS
13h 10m
2 stops
$536Southwest
jue., abr. 30 - jue., may. 7
Southwest Logo
8:00 pm - 1:15 pm
COS
-
NAS
15h 15m
2 stops
Southwest Logo
8:45 am - 9:45 pm
NAS
-
COS
15h 00m
2 stops
$571Southwest
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 United Airlines ($336) and Delta ($409).

Good to know

Low seasonSeptember
Cheapest flight$168
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 4337 reviews
8.0Comfort
8.6Crew
8.1Boarding
7.0Food
7.5Entertainment
Airline reviews

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

2.0 MediocreCourtenay, Apr 2026
DAL - CLT
Read more Southwest reviews

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

It was good from LAX to Phoenix, But the connection in Phoenix to Tulsa was not that great. The staff on both flights were great. The choice of free entertainment was ok nothing to brag about. The 45 min delay because of some electrical issue wasn't great from Phoenix to Tulsa. We sat there with hardly any air, The seat I had was between windows so the side of the plane pushed in on you. My being a bigger man it then made the seating area uncomfortable. The seats on the plane had no power to connect to recharge your phone or anything. I would recommend that they should look into a slot or clamp to hold your phone to enjoy while watching the entertainment choices hands-free. Also make it possible to raise the inner seat by the window be able to raise the arm rest up to make more room for larger people to set more comfortably. I would also say other then that stop price gouging the airfare or nickel and diming everything. Not fair for people having to fly for emergencies and be paying for higher prices due to the season or holidays. Your making your money either way and the cost of flying is still going to be the same regardless if there's 100 people or 200 people.

Had a great flight. Delayed takeoff, but comfortable. Snacks were good.

Love them will get a Southwest card to track my points and keep flying with them. My family and I were pleased with the services.

I have roller bag with food and medication told me I couldn't bring on my 2nd flight today. 15 years flying with SW never an issue with that bag.

Southwest continues to do less for more money. Flight attendants used to be fun and friendly. But now it’s like they don’t even see you. Such a shame.

Great flight. Good snacks and drinks. Grateful it was free. The flight from Nashville to louisville, i think her name was Tracy (not sure that's right) super awesome, nice and cheerful. She really enjoyed being at work today! She was the person who scanned the boarding pass on flight wn941. She should be recommended for a raise !

I liked it better when you were truer to your roots Am paying more for less fun

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.

Everything could have benn better. Short fly, no food, no entertainment and no wifi.

Flight delayed. Air broken. Cabin was hot enough to pass out. Delta shuttle’s becoming worse and worse.

my mom urmila patel needed a wheelchair which was not available on the curbside. she needed to walk almost 50 meters inside (at the risk of falling) and then had to wait in line to get a wheelchair (this is not ok). Once obtained she had to seat in it for 30-45 minutes for someone to take her in thru the checkin process (which was fairly smooth and easy). the lady who helped her with her checkin process was very courteous and helpful

On the return flight, flight attendant Britt went out of her way to inform passengers that several of us had tight connections.

Fast, lovely scenery, great info on the Delta flight screen about landmarks we were flying over. Great landing!

Staff at the check-in counter were friendly, happy and helpful. They tagged our bags and sent us to “bag drop off” but were not very clear about where that was. The airport was busy we headed off in what we thought was the right direction until a gentleman waved us down and actually came after us. He was the baggage handler for Delta and recognized our “deer in the headlights “ look-he brought us to the right area (which was marked as the Southwest Airlines Drop Off) and sent us on our way. Wonderful guy, low key and working with a big smile on his face. Loved it. Loved him.

During the flight, the only refreshments provided were crackers and soft drinks; no substantial food was offered despite the international route. Furthermore, our initial flight was delayed, causing us to miss the connecting flight in Atlanta. The airline did not hold the connection, and we were informed that the next available flight is not for another 24 hours. While I am aware of alternative options via JetBlue, they operate out of JFK, which is not a viable solution for us as a resident of New Jersey.

Arlene was a great flight attendant. I also liked how one of the other flight attendants gave us a heads up about snacks and asked everyone to remove their headphones when it was their turn to order. Good idea.

Long flight but comfortable and not freezing as I have experienced on Hawaiian flights to the islands. They gave us blankets just in case. Nice touch.

I haven’t flown economy in over 20 years but it was not bad. Room by my feet for my bag and seat was roomy enough. Surprised in a good way.

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.

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.

Flight was delayed. No urgency by American Airlines team to assist those with connecting flights. It was basically you are on your own to run through the terminals to try and make your connection. Thanks, Mary

I have never been assaulted they way I was today in Charlotte - shame on American

One of our group members was struggling to walk. In Charlotte we asked for a wheelchair and she was accompanied by Desmond. I was impressed by his patience and attention. In Boston she received the same service. I didn’t get the name of the helper but she went above and beyond in assisting us. A great AA service

Better snacks but flight and crew were amazing on this flight

Found that the plane used for this short flight is smaller and therefore the seats are really squeezed tight.

It was the most un-special flight experience in my life.

Plane was super cold. No entertainment unless you were with mileage program Getting off the plane was super slow

Flight was on-time, boarding was flawless and the crew was friendly.

The staff are very, very professional. It's what flying should feel like.

Flight boarded from Gate 159B, the farthest gate in the LAX Bradley Terminal. While the flight operated on time, the first class cabin attendant made no recognition of my being an Advantage Executive Platinum member.

Everything you need to know for your flight to Caribbean

Information on your arrival and departure airports