$238 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 5/27. 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.
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Best Caribbean Flight Deals from Colorado Springs

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours

Punta Cana
Punta Cana2 stops$493
Santo Domingo
Santo Domingo2 stops$491
Montego Bay
Montego Bay1 stop$505
Oranjestad
Oranjestad2 stops$516
Aguadilla
Aguadilla2 stops$730
Punta Cana
Punta Cana2 stops$493
Santo Domingo
Santo Domingo2 stops$491
Montego Bay
Montego Bay1 stop$505
Oranjestad
Oranjestad2 stops$516
Aguadilla
Aguadilla2 stops$730

Cheap Flight Deals from Colorado Springs to Caribbean (COS-0CB)

 
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.

Recent round-trip flight deals from Colorado Springs to Caribbean

Recommended round-trip deals departing in the coming months from the most popular airlines that fly from Colorado Springs to Caribbean.
Discover the best prices for you by selecting your travel dates on KAYAK.
American Airlines Logo
4:43 pm - 2:40 pmCOS-SJU
19h 57m2 stops
American Airlines Logo
12:59 am - 10:00 amSJU-COS
11h 01m1 stop
$482American Airlines
Find Deal
Mon, Jun 2 - Tue, Jun 17
American Airlines Logo
6:00 am - 8:47 pmCOS-SDQ
12h 47m2 stops
American Airlines Logo
7:20 pm - 10:01 amSDQ-COS
16h 41m2 stops
$491American Airlines
Find Deal
Wed, Jun 4 - Tue, Aug 5
Delta Logo
6:00 am - 12:19 amCOS-SDQ
16h 19m2 stops
Delta Logo
2:47 pm - 9:03 pmSDQ-COS
8h 16m1 stop
$501Delta
Find Deal
Tue, Jun 3 - Thu, Jul 24
United Airlines Logo
2:35 pm - 5:30 amCOS-SJU
12h 55m2 stops
United Airlines Logo
1:05 am - 11:08 amSJU-COS
12h 03m2 stops
$508United Airlines
Find Deal
Mon, Jun 2 - Wed, Jun 4
United Airlines Logo
12:04 pm - 11:54 pmCOS-SJU
9h 50m1 stop
United Airlines Logo
1:05 am - 10:54 amSJU-COS
11h 49m2 stops
$520United Airlines
Find Deal
Wed, Jun 11 - Mon, Jun 16
Delta Logo
6:00 am - 3:34 pmCOS-MBJ
8h 34m1 stop
Delta Logo
1:09 pm - 9:03 pmMBJ-COS
8h 54m1 stop
$525Delta
Find Deal
Wed, Jul 23 - Wed, Jul 30
Southwest Logo
11:30 am - 11:05 pmCOS-SJU
9h 35m2 stops
Southwest Logo
8:00 am - 4:10 pmSJU-COS
10h 10m2 stops
$545Southwest
Find Deal
Fri, Aug 1 - Tue, Aug 5
 Logo
10:15 am - 7:07 pmCOS-SJU
30h 52m3 stops
 Logo
8:12 pm - 5:00 pmSJU-COS
22h 48m3 stops
Fri, May 30 - Sun, Jun 8
 Logo
10:15 am - 7:07 pmCOS-SJU
30h 52m3 stops
 Logo
1:39 pm - 9:15 amSJU-COS
21h 36m2 stops
Fri, May 30 - Sun, Jun 8
Southwest Logo
9:25 am - 12:10 amCOS-SJU
12h 45m1 stop
Southwest Logo
6:00 am - 5:05 pmSJU-COS
13h 05m2 stops
$635Southwest
Find Deal
Sat, Jun 28 - Sun, Jul 6
Useful Info

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 $498 (return) on average. On the other hand, the most expensive months are March and June, when the average cost of round-trip tickets is $728 and $688 respectively.

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

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

Your flight ticket price will generally be cheaper if you fly to Caribbean on a Monday and more expensive on a Friday. On your return trip to Colorado Springs, you should consider flying back on a Friday, and avoid Sundays for better deals.

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

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, 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, you should book around 2 weeks before departure. For the absolute cheapest price, our data suggests you should book 21 weeks before departure.


Good to know

Low seasonJune
High seasonApril
Cheapest flight$238
Best time to beat the crowds but there is an average 36% increase in price.
Most popular time to fly and prices are also 5% lower on average.
Flight from Colorado Springs to Santo Domingo

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.

  • What is the cheapest time of day to fly to Caribbean?

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

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 4294 reviews
8.2Boarding
7.6Entertainment
8.0Comfort
7.1Food
8.6Crew
Airline reviews

It is southwest seat was ok. Not the most comfortable seat

8.0 ExcellentJohn, Apr 2025PVD - FLL
Read more Southwest reviews

It is southwest seat was ok. Not the most comfortable seat

I’ve always loved Southwest. No issues at all. I was flying standby and the gate agent was extremely friendly and helpful. Boarding was smooth and I was able to get a window seat in the emergency exit row. Crew was fantastic! They were very professional and accommodating. We had to divert from our destination due to weather but the flight crew kept everyone at ease and informed us of all pertinent information. Excellent flight

The price of the tickets isn't matching the flight experience. No matter how long the flight is, you're only getting pretzels. The flight attendants looked unkept and over it.

Plz don't take away free bags and free seating

The seats were a bit cramped and worn, but otherwise okay.

I would have liked to arrive on time - not 5 hours late!

After a 3 hour layover in Denver my flight was delayed over 5 hours! No explanation; no assistance; no offer to provide compensation; no one at Southwest was willing to offer any assistance. 8 hours in the Denver airport - ridiculous!

It was a perfect flight in all aspects! Both legs!

Only one drink pass through the cabin for a 4 hour flight. Quite rough and bumpy landing.

Boarding process, crew were good. But the seats were so uncomfortable that was all I could focus on. I literally had to sit forward so that all 3 of us could fit in row. I will try to avoid Southwest in the future for any flights over 60 minutes.

Our bag was lost so that made unnecessary chaos On our trip

Delta is my preferred airline. I've traveled with them for years. On time in most cases, good communication, easy to use app. Most planes are pretty nice. I was on a CRJ 700/900 however, which was pretty badly aged inside and needed a refresh. No infotainment, unreliable wifi, best to download before boarding or bring a book. Food choices are really just snacks on this flight, nice variety but about what you'd expect. Great staff and prompt in departure and early arrival too. Overall quite satisfied.

Crew was friendly Love the entertainment in the seat head rest.

Delta flight was on time, seats were comfortable, and crew was nice.

This had nothing to do with Delta… The flights were on time and flawless. The service was excellent. We purchased seats in (aisle/middle) comfort plus since this was a cross country flight. Unfortunately, the woman seated at the window was 300+ pounds and, as might be expected, covered up about a third of the middle seat also. there was absolutely nothing that Delta could have done about that… I just don’t know what the answer should be. If you purchase a seat, you should should be able to use the entire seat and not just the portion that someone else is not sitting/oozing in. Disappointing…there should be something that could be done….I'm just not sure what solution could be.

Delayed take-off. Very small plane so very scary with lots of bumps during the flight. Would never fly Delta on short flights in small 80 seaters plane again! Felt relieved when landed.

The worst part was I was NOT allowed in the lounge even though I was holding a first class ticket and have a premium American Express card. I have flown Business or First Class with many airlines. Delta is the ONLY one who does not extend this courtesy to anyone except people who hold the very expensive American Express card. As a result, I won’t fly Delta if I have any other choice.

It was an overnight flight and I desperately needed coffee before we landed, but Delta does only one beverage service, and that is shortly after takeoff, not before landing at 5 am.

A little bumpy ride . No food was being provided due the the turbulence. That was ok it was a short flight to my standards.

Simply outstanding. Their new lounge for Delta One customers is a cut above the rest.

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.

Overall, it was a good experience. Boarding was good and there was plenty of overhead bin space for everyone’s carryons (even when we boarded toward the end). Only improvement would be to offer trash service more regularly.

David went above and beyond to make our flight the best that it could be

No food service almost missed because of first flight delays

Had a hard time finding my assigned seat. No attendants to assist.

Several delays. Next flight was worse. Did not arrive home until 2am PT

Very helpful ground crew after an earlier flight delay and being rebooked on a different flight.

Everything about the flight was lovely…We left early, arrived early, cabin crew were efficient and helpful. Flight was easy and most pleasant.

First world problems, but still… We were seated in first class and asked for a cocktail on a very short, 50 minute flight. After our drink order was taken, a half hour went by, and we noticed that every other person in the small plane had been served except for us. We got up to ask about it, the drinks finally came, then were taken away three minutes later since the flight was so short. Really strange situation, on the other hand, we were in Utah.

We missed our flight. The boarding pass had the wrong gate and by the time we received the text from Kayak, our flight was already gone. I’ll never use Kayak again and will go direct to the airlines in the future.

Boarding took forever, the plane was cramped and cold, and the seatbelt song came on constantly throughout the red eye flight with a loud pre-recorded message playing each time

Cabin felt crammed Snacks are lame But crew was super efficient getting us out on time despite delay

Took off on time and successfully avoided weather that looked to be a problem along the way

There were five broken seats on the plane. The crew was very rude in telling people they had to get off the plane and get a flight the next day. No call for volunteers, but telling people they had to get off. One woman was flying with her elderly mother and daughter and was told she had to leave or all three had to leave. Fortunately, a volunteer offered to stay. The situation was handled poorly.

The flight to Tokyo AA61 took off about two hours late, but then had to turn back. By that time the crew had to be replaced. Then they kept promising to take off in an hour, then in 3, then switch to the next day.

Everything you need to know for your flight to Caribbean

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