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$151+ Cheap flights from Colorado Springs (COS) to Caribbean

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 8/19. Fares are subject to change and may not be available on all flights or dates of travel.
COS — SJU
Jul 8 — Jul 151
Tue 7/8
Tue 7/15
1 adult, Economy
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Cheap flight deals from Colorado Springs to Caribbean

Keep the following information in mind while searching for Colorado Springs to Caribbean flight deals. Data was last updated July 3, 2025.

Round-trip from

$301
(Southwest)

One-way from

$151
(Southwest)

Popular in

December

Cheapest in

October

Average price

$411
From Colorado Springs to Caribbean
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One-way flight from Colorado Springs to Caribbean
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Highest demand for flights based on searches. 19% potential increase in price ($109 potential increase over avg. RT price).
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Cheapest flight prices on average. 5% potential price decrease ($23 potential savings vs. average RT price).
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Average for round-trip flights in July 2025
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Find flight deals from Colorado Springs to Caribbean

Cheapest flights from Colorado Springs to Caribbean
Explore the most affordable flight options available from Colorado Springs to Caribbean. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 3, 2025.

This Southwest deal was found by Cheapflights users on 7/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/1711:15 amCOS - SJU
1 stop9h 15mSouthwest
Wed 9/247:20 amSJU - COS
1 stop12h 05mSouthwest
Deal found 7/1$301
This United Airlines deal was found by Cheapflights users on 7/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/306:00 amCOS - SJU
1 stop9h 25mUnited Airlines
Fri 11/72:25 pmSJU - COS
1 stop10h 34mUnited Airlines
Deal found 7/2$326
This American Airlines deal was found by Cheapflights users on 7/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/294:55 pmCOS - SJU
1 stop10h 11mAmerican Airlines
Thu 7/316:15 amSJU - COS
1 stop18h 07mAmerican Airlines
Deal found 7/3$369
This Delta deal was found by Cheapflights users on 7/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/246:00 amCOS - SJU
1 stop8h 18mDelta
Sat 11/12:28 pmSJU - COS
1 stop8h 52mDelta
Deal found 7/1$375
This Delta deal was found by Cheapflights users on 7/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/211:40 pmCOS - MBJ
2 stops20h 58mDelta
Tue 10/281:03 pmMBJ - COS
2 stops24h 54mDelta
Deal found 7/2$419
This American Airlines deal was found by Cheapflights users on 7/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/3012:07 pmCOS - MBJ
1 stop23h 24mAmerican Airlines
Thu 9/41:05 pmMBJ - COS
1 stop10h 03mAmerican Airlines
Deal found 7/2$423
This Delta deal was found by Cheapflights users on 7/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/55:55 pmCOS - PUJ
2 stops18h 39mDelta
Fri 9/121:57 pmPUJ - COS
2 stops32h 42mDelta
Deal found 7/3$447
This American Airlines deal was found by Cheapflights users on 7/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/611:01 amCOS - POP
2 stops23h 34mAmerican Airlines
Sat 9/131:35 pmPOP - COS
2 stops22h 35mAmerican Airlines
Deal found 7/3$493
This American Airlines deal was found by Cheapflights users on 6/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/115:07 pmCOS - PUJ
2 stops19h 23mAmerican Airlines
Tue 12/164:05 pmPUJ - COS
2 stops20h 09mAmerican Airlines
Deal found 6/30$493
This United Airlines deal was found by Cheapflights users on 6/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/111:30 pmCOS - PUJ
1 stop25h 48mUnited Airlines
Tue 12/162:05 pmPUJ - COS
1 stop9h 53mUnited Airlines
Deal found 6/30$548
This American Airlines deal was found by Cheapflights users on 7/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/155:24 pmCOS - UVF
2 stops19h 11mAmerican Airlines
Fri 8/223:35 pmUVF - COS
2 stops20h 27mAmerican Airlines
Deal found 7/1$556
This Southwest deal was found by Cheapflights users on 7/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/256:35 pmCOS - MBJ
2 stops19h 25mSouthwest
Fri 8/812:45 pmMBJ - COS
2 stops10h 50mSouthwest
Deal found 7/3$581

Cheapflights Fare Finder

Customize your flight search to find flights from Colorado Springs to Caribbean that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated July 3, 2025.
Use the filters below to find and compare flights from Colorado Springs to Caribbean that are best for you.

Fly from

Colorado Springs

Fly to

Caribbean

Route

Depart

Return

Price

Colorado SpringsSan Juan

COS - SJU

COSSJU

Colorado Springs

Wed 9/17

11:15 am-10:30 pm

1 stop9h 15m

San Juan Luis Munoz Marin Intl

Wed 9/24

7:20 am-5:25 pm

1 stop12h 05m

$301

Colorado SpringsSan Juan

COS - SJU

COSSJU

Colorado Springs

Thu 10/30

6:00 am-5:25 pm

1 stop9h 25m

San Juan Luis Munoz Marin Intl

Fri 11/7

2:25 pm-9:59 pm

1 stop10h 34m

$326

Colorado SpringsSan Juan

COS - SJU

COSSJU

Colorado Springs

Tue 7/29

4:55 pm-5:06 am

1 stop10h 11m

San Juan Luis Munoz Marin Intl

Thu 7/31

6:15 am-10:22 pm

1 stop18h 07m

$369

Colorado SpringsSan Juan

COS - SJU

COSSJU

Colorado Springs

Fri 10/24

6:00 am-4:18 pm

1 stop8h 18m

San Juan Luis Munoz Marin Intl

Sat 11/1

7:30 am-7:38 pm

2 stops14h 08m

$375

Colorado SpringsMontego Bay

COS - MBJ

COSMBJ

Colorado Springs

Tue 10/21

1:40 pm-11:38 am

2 stops20h 58m

Montego Bay Sangster Intl

Tue 10/28

1:03 pm-12:57 pm

2 stops24h 54m

$419

Colorado SpringsMontego Bay

COS - MBJ

COSMBJ

Colorado Springs

Sat 8/30

12:07 pm-12:31 pm

1 stop23h 24m

Montego Bay Sangster Intl

Thu 9/4

1:05 pm-10:08 pm

1 stop10h 03m

$423

Colorado SpringsPunta Cana

COS - PUJ

COSPUJ

Colorado Springs

Fri 9/5

5:55 pm-2:34 pm

2 stops18h 39m

Punta Cana

Fri 9/12

1:57 pm-8:39 pm

2 stops32h 42m

$447

Colorado SpringsPuerto Plata

COS - POP

COSPOP

Colorado Springs

Sat 9/6

11:01 am-12:35 pm

2 stops23h 34m

Puerto Plata La Union

Sat 9/13

1:35 pm-10:10 am

2 stops22h 35m

$493

Colorado SpringsPunta Cana

COS - PUJ

COSPUJ

Colorado Springs

Thu 12/11

5:07 pm-3:30 pm

2 stops19h 23m

Punta Cana

Tue 12/16

4:05 pm-9:14 am

2 stops20h 09m

$493

Colorado SpringsPunta Cana

COS - PUJ

COSPUJ

Colorado Springs

Thu 12/11

1:30 pm-6:18 pm

1 stop25h 48m

Punta Cana

Tue 12/16

2:05 pm-8:58 pm

1 stop9h 53m

$548

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/2

Showing 1-10 of 29 results
1
2
3

Best time to book a flight from Colorado Springs to Caribbean

Have a flexible travel schedule? Discover the best time to fly to Caribbean from Colorado Springs with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Colorado Springs to Caribbean

What is the cheapest month to book a flight from Colorado Springs to Caribbean?

Currently, September is the cheapest month in which you can book a flight from Colorado Springs to Caribbean (average of $254). Flying from Colorado Springs to Caribbean in June is currently the most expensive (average of $339). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

Reviews of airlines servicing Caribbean

Get insights into the airlines that provide service to Caribbean. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Caribbean. Reviews last updated July 3, 2025.
Get a feel of what it's like to fly with Southwest, Delta, and United Airlines from Colorado Springs to Caribbean by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,266 reviews

Boarding

8.2

Crew

8.6

Overall

8.0

Entertainment

7.6

Comfort

8.0

Food

7.0

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Southwest
8.0
Very good
4,266 reviews
Southwest
8.0
Very good
4,266 reviews

Boarding

8.2

Crew

8.6

Overall

8.0

Entertainment

7.6

Comfort

8.0

Food

7.0

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Delta
8.0
Very good
7,982 reviews
Southwest
8.0
Very good
4,266 reviews

Boarding

8.2

Crew

8.6

Overall

8.0

Entertainment

7.6

Comfort

8.0

Food

7.0

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
United Airlines
7.4
Good
8,861 reviews
Southwest
8.0
Very good
4,266 reviews

Boarding

8.2

Crew

8.6

Overall

8.0

Entertainment

7.6

Comfort

8.0

Food

7.0

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,266 reviews

Boarding

8.2

Crew

8.6

Overall

8.0

Entertainment

7.6

Comfort

8.0

Food

7.0

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.

Related info for your journey

Find useful and relevant information for your journey from Colorado Springs to Caribbean. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly from for flights from Colorado Springs to Caribbean?

    Colorado Springs (COS) is the airport you will fly out of if you book a flight from Colorado Springs to Caribbean. It is only a 6.7 mi journey to Colorado Springs (COS) from Colorado Springs’s city center.

  • What are the cheapest airlines to fly from Colorado Springs to Caribbean one-way?

    The cheapest airlines for a one-way flight from Colorado Springs to Caribbean are Southwest ($151), Delta ($188), and American Airlines ($219).

  • What are the most popular routes from Colorado Springs to Caribbean?

    Most travelers choose Colorado Springs - San Juan Luis Munoz Marin Intl, Colorado Springs - Montego Bay Sangster Intl or Colorado Springs - Punta Cana when deciding on the best route from Colorado Springs to Caribbean.

  • Can I find deals for flights from Colorado Springs to Caribbean that include hotel bookings?

    Yes. In addition to deals on Colorado Springs to Caribbean flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Colorado Springs to Caribbean?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Colorado Springs to Caribbean.

  • Can I find deals for business class flights from Colorado Springs to Caribbean?

    Yes. Cheapflights offers flight deals from Colorado Springs to Caribbean by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Colorado Springs to Caribbean?

    Currently, September is the cheapest month in which you can book a flight from Colorado Springs to Caribbean (average of $254). Flying from Colorado Springs to Caribbean in June is currently the most expensive (average of $339). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

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Top 4 airlines flying from Colorado Springs to Caribbean

Discover the top 4 airlines that operate flights from Colorado Springs to Caribbean. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated July 3, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$192Average$600FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$362Average$626FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$391Average$546FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$430Average$546FlexibilityNo cancel feeOn-time63%

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