$123 Find Cheap Flights from Colorado Springs to Caribbean Islands

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 Islands departing on 8/19. 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

KAYAK searches hundreds of travel sites at once for deals on flights to Caribbean Islands

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Colorado Springs to Caribbean Islands, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Colorado Springs to Caribbean Islands, as well as popular online travel agencies
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Cheap Flights from Colorado Springs to Caribbean Islands

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$609
Montego Bay
Montego Bay2 stops$507
Oranjestad
Oranjestad2 stops$488
Nassau
Nassau2 stops$559
Providenciales
Providenciales2 stops$548
Bridgetown
Bridgetown2 stops$696
George Town
George Town2 stops$482
Punta Cana
Punta Cana2 stops$491
Santo Domingo
Santo Domingo2 stops$609
Montego Bay
Montego Bay2 stops$507
Oranjestad
Oranjestad2 stops$488
Nassau
Nassau2 stops$559
Providenciales
Providenciales2 stops$548
Bridgetown
Bridgetown2 stops$696
George Town
George Town2 stops$482

Book Cheap Colorado Springs to Caribbean Islands 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 Islands 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 Islands

Tue, Jan 13 - Thu, Jan 29
American Airlines Logo
5:11 pm - 3:45 pmCOS-SJU
19h 34m2 stops
American Airlines Logo
6:50 pm - 9:10 amSJU-COS
17h 20m2 stops
$245American Airlines
Find Deal
Sun, Dec 7 - Wed, Dec 24
American Airlines Logo
6:13 am - 8:55 pmCOS-SJU
11h 42m1 stop
American Airlines Logo
2:45 pm - 11:29 pmSJU-COS
11h 44m2 stops
$309American Airlines
Find Deal
Tue, Sep 30 - Sat, Oct 4
United Airlines Logo
7:30 am - 5:30 pmCOS-SJU
8h 00m1 stop
United Airlines Logo
2:00 pm - 9:54 pmSJU-COS
9h 54m1 stop
$335United Airlines
Find Deal
Tue, Sep 9 - Sat, Sep 13
Southwest Logo
11:15 am - 10:30 pmCOS-SJU
9h 15m1 stop
Southwest Logo
7:45 am - 7:05 pmSJU-COS
13h 20m2 stops
$346Southwest
Find Deal
Tue, Sep 30 - Fri, Oct 3
United Airlines Logo
7:30 am - 5:30 pmCOS-SJU
8h 00m1 stop
United Airlines Logo
1:05 am - 10:40 amSJU-COS
11h 35m2 stops
$375United Airlines
Find Deal
Mon, Oct 27 - Fri, Oct 31
Delta Logo
1:16 pm - 12:28 pmCOS-STI
21h 12m2 stops
Delta Logo
9:03 pm - 6:11 pmSTI-COS
23h 08m2 stops
$483Delta
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Fri, Sep 12 - Tue, Sep 16
Southwest Logo
10:35 am - 11:50 pmCOS-SJU
11h 15m2 stops
Southwest Logo
7:20 am - 5:25 pmSJU-COS
12h 05m1 stop
$487Southwest
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Thu, Sep 25 - Mon, Sep 29
Delta Logo
5:55 pm - 11:36 amCOS-GCM
16h 41m2 stops
Delta Logo
12:52 pm - 8:39 pmGCM-COS
8h 47m1 stop
$494Delta
Find Deal
Sun, Aug 17 - Sat, Aug 23
 Logo
5:30 am - 11:05 amCOS-MBJ
28h 35m2 stops
 Logo
12:45 pm - 1:14 pmMBJ-COS
25h 29m3 stops
$2,043
Find Deal
Sat, Nov 1 - Fri, Nov 7
 Logo
9:30 am - 4:05 pmCOS-POP
28h 35m3 stops
 Logo
2:50 pm - 3:38 pmPOP-COS
27h 48m2 stops
$2,105
Find Deal
Booking Insights

KAYAK's insights & trends for Colorado Springs to Caribbean Islands flights

Get data-powered insights and trends into flights from Colorado Springs to Caribbean Islands to help you find the cheapest flights, the best time to fly and much more.

Can I save money by flying with a layover from Colorado Springs to Caribbean Islands?

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

No, with an average price for the route of $505, prices are generally cheapest when you fly direct.

What is the cheapest month to fly from Colorado Springs to Caribbean Islands?

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 Islands, 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 Islands is October, when tickets cost $480 (return) on average. On the other hand, the most expensive months are December and March, when the average cost of round-trip tickets is $786 and $734 respectively.

What’s the cheapest day of the week to fly from Colorado Springs to Caribbean Islands?

The average price of all round-trip flights from Colorado Springs to Caribbean Islands clicked on KAYAK for each day over the last 12 months.

If your flying dates are flexible, you should consider flying to Caribbean Islands on a Monday, as we generally find the cheapest rates on that day for this route. On the other hand, Friday is the most expensive day to fly from Colorado Springs to Caribbean Islands. For your return ticket, we recommend flying on a Friday and avoiding Sundays for the best deals.

How far in advance should I book a flight from Colorado Springs to Caribbean Islands?

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 Islands, 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 Islands, you should book around 2 weeks before departure, which saves you about 11% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 21 weeks before departure.


Good to know

Low seasonJune
Cheapest flight$123
Best time to beat the crowds but there is an average 23% increase in price.
Most popular time to fly and prices are also 6% lower on average.
Flight from Colorado Springs to San Juan

FAQs - booking Caribbean Islands flights

  • How does KAYAK find such low prices on flights from Colorado Springs to Caribbean Islands?

    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 Islands.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Colorado Springs to Caribbean Islands?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Colorado Springs to Caribbean Islands 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 Islands?

    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 Islands 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 Islands?

    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 Islands 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 Islands?

    The cheapest time of day to fly to Caribbean Islands 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 Islands is generally in the morning, which is peak travel time and where the average cost of a ticket is $576.

Reviews of the top 3 airlines serving from Colorado Springs to Caribbean Islands

 
See real verified KAYAK customer reviews for airlines flying from Colorado Springs to Caribbean Islands. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Colorado Springs to Caribbean Islands? 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
DeltaOverall score based on 7980 reviews
7.3Food
7.9Entertainment
7.9Comfort
8.2Boarding
8.5Crew
Airline reviews

Delayed and took off even later than the scheduled delay time

8.0 ExcellentAnonymous, Jul 2025DTW - SEA
Read more Delta reviews

Delayed and took off even later than the scheduled delay time

For a 69 year old with health problems I had the worse experience, no wheelchair when I entered a lady told me to sit and wait while a gentleman told me I had to walk to the Delta station, which I did. I had a carry on and a bag, and I was traveling with my service dog, which was on his carrier and the lady charged me for my carry on luggage, beside all the waiting cause of the delay, I had to walk to get my luggage cause no wheelchair showed up, I am so disappointed. I will get in touch with the company. I got home at 3:00 am, not good for my health situation.

Only issue was with seating. The economy fare we purchased did say there was no guarantee the three people in our party would be seated together, and we were not. At the gate, the agent told us more specifically, the fare we purchased meant we would be seated in middle seats only. This should just be made more obvious.

Great experience on Delta. Staff from baggage check to flight attendants were very courteous and professional. My only issue was a personal preference for pretzels instead of the chips and cookies that were offered.

There was no problems, just a little uncomfortable with seats that do not lay back a little

Always good but we must do something about people in rows ahead of you that don't put their seats back up when they are suppose to. And It's rough to not be able to even lean over to get something out of my purse.

Flight was delayed, 30+ bags had to be gate checked. Crew were very friendly!

Everything was good until we were boarding our connection flight in Atlanta, we were told to gate check our carry-on, but when we got inside the plane, there was plenty of room in the overhead.

Did not know my son and I had different seating arrangements. He was fine, but it was disappointing.

Flight was canceled, and no effort was made to help with rebooking, no hotel vouchers, no car transportation and minimal food voucher and most places for food were closed by the time the voucher was given. Waited for 3 hours for bags. Simply the worst travel experience I have ever had

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.

Electric plugs didn't work. Entertainment system wasn't working

The design of the light switch on the arm rest is ridiculous.

The gate attendant let me walk right by her with a bag too big for the overhead compartment

Overall poor for me I paid extra for seats with leg room and my regional flights exit row seats have less leg room then the others that's money that could have been saved and on my final flight home the flights air was not operating it was unbearably hot in the cabin I will be contacting United and filing a DOT complaint

I don’t understand the purpose of the orange “priority” tag on my bag. This tagged, my bag is last or near to the last bag to come down the carousel at IAH.

Very poor delay in dfw was really bad n long

Our flight was 1.5 hours delayed. There was no weather for the inbound flight, so I don't understand why. This meant a VERY late arrival and only a quick nap before my morning flight.

Because of rescheduling, they had to put me on a flight that didn't go through Dallas

It was very difficult to stretch my knee out and I am very short. I also had a torn tendon in my knee which made it extra uncomfortable anyways. My husband is 6'2" and I can't imagine him flying in that plane.

3 hour weather delay followed by 1 hour (and counting) maintenance delay. UGH!

Couldn’t get the door on the plane to close leading to a nearly 2 hour delay. But, hey at least they didn’t cancel the flight.

Flight was cancelled 3 hrs AFTER etd. Thetefore Missed connection from JFK to New Zealand . No accommodation provided… This cost ne aporox 1000 USD in extra expenses and turned whst should have been a 24 hr trip ftom Boston - New Zealand into a VERY expensive , late 70+ hr nightmare … Complete nonsense!!!

After we'd boarded , they canceled the flight. The crew didn't even know , we just all received text messages. Then after they deplaned us , AA was just like "too bad, go F your self, we sure ain't gonna help you"

The plane was broken so we had to change planes.

The flight got delayed 2.5 hrs due to a maintenance issue that cause a domino effect. American should have spare planes for when something like this happens.

Everything you need to know for your flight to Caribbean Islands

Information on your arrival and departure airports

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