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$123+ 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 9/29. Fares are subject to change and may not be available on all flights or dates of travel.
COS — SJU
Aug 25 — Sep 11
Mon 8/25
Mon 9/1
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 August 20, 2025.

Round-trip from

$245
(United Airlines)

One-way from

$123
(American Airlines)

Popular in

December

Cheapest in

October

Average price

$338
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. 18% potential increase in price ($105 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($21 potential savings vs. average RT price).
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Average for round-trip flights in August 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 August 20, 2025.

This United Airlines deal was found by Cheapflights users on 8/19. 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.
Tue 10/286:00 amCOS - SJU
1 stop9h 25mUnited Airlines
Tue 11/188:30 amSJU - COS
2 stops12h 10mUnited Airlines
Deal found 8/19$245
This American Airlines deal was found by Cheapflights users on 8/20. 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 10/285:01 pmCOS - SJU
2 stops17h 38mAmerican Airlines
Tue 11/186:42 pmSJU - COS
2 stops20h 03mAmerican Airlines
Deal found 8/20$325
This United Airlines deal was found by Cheapflights users on 8/18. 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.
Sat 9/67:40 amCOS - SJU
1 stop10h 58mUnited Airlines
Fri 9/121:05 amSJU - COS
2 stops11h 51mUnited Airlines
Deal found 8/18$455
This American Airlines deal was found by Cheapflights users on 8/20. 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 11/75:17 pmCOS - SJU
2 stops17h 24mAmerican Airlines
Mon 11/106:44 amSJU - COS
1 stop12h 03mAmerican Airlines
Deal found 8/20$464
This American Airlines deal was found by Cheapflights users on 8/18. 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.
Wed 9/2411:01 amCOS - STI
2 stops23h 26mAmerican Airlines
Sat 9/271:29 pmSTI - COS
2 stops22h 41mAmerican Airlines
Deal found 8/18$483
This American Airlines deal was found by Cheapflights users on 8/18. 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.
Mon 10/136:02 amCOS - PUJ
1 stop7h 37mAmerican Airlines
Mon 10/204:23 pmPUJ - COS
1 stop19h 23mAmerican Airlines
Deal found 8/18$489
This Delta deal was found by Cheapflights users on 8/18. 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 9/125:55 pmCOS - PUJ
2 stops16h 37mDelta
Sat 9/201:57 pmPUJ - COS
2 stops24h 09mDelta
Deal found 8/18$491
This United Airlines deal was found by Cheapflights users on 8/18. 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.
Mon 9/226:25 pmCOS - MBJ
2 stops16h 18mUnited Airlines
Sat 9/272:40 pmMBJ - COS
1 stop8h 01mUnited Airlines
Deal found 8/18$503
This Delta deal was found by Cheapflights users on 8/18. 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 10/211:16 pmCOS - MBJ
2 stops21h 07mDelta
Tue 10/2812:48 pmMBJ - COS
2 stops24h 23mDelta
Deal found 8/18$507
This American Airlines deal was found by Cheapflights users on 8/18. 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.
Mon 9/226:02 amCOS - MBJ
1 stop7h 03mAmerican Airlines
Sat 9/271:05 pmMBJ - COS
1 stop22h 05mAmerican Airlines
Deal found 8/18$511
This American Airlines deal was found by Cheapflights users on 8/18. 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 10/216:02 amCOS - MBJ
1 stop7h 13mAmerican Airlines
Tue 10/282:00 pmMBJ - COS
1 stop22h 34mAmerican Airlines
Deal found 8/18$512
This American Airlines deal was found by Cheapflights users on 8/18. 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 10/25:03 pmCOS - MBJ
2 stops19h 35mAmerican Airlines
Mon 10/61:00 pmMBJ - COS
1 stop21h 46mAmerican Airlines
Deal found 8/18$515

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 August 20, 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

Tue 10/28

6:00 am-5:25 pm

1 stop9h 25m

San Juan Luis Munoz Marin Intl

Tue 11/18

8:30 am-5:40 pm

2 stops12h 10m

$245

Colorado SpringsSan Juan

COS - SJU

COSSJU

Colorado Springs

Fri 11/7

5:17 pm-1:41 pm

2 stops17h 24m

San Juan Luis Munoz Marin Intl

Mon 11/10

6:42 pm-11:45 am

2 stops20h 03m

$325

Colorado SpringsSan Juan

COS - SJU

COSSJU

Colorado Springs

Tue 10/28

5:01 pm-12:39 pm

2 stops17h 38m

San Juan Luis Munoz Marin Intl

Tue 11/18

6:42 pm-11:45 am

2 stops20h 03m

$325

Colorado SpringsSan Juan

COS - SJU

COSSJU

Colorado Springs

Fri 1/9

5:11 pm-3:45 pm

2 stops19h 34m

San Juan Luis Munoz Marin Intl

Sun 1/18

6:45 am-9:44 pm

1 stop17h 59m

$365

Colorado SpringsSan Juan

COS - SJU

COSSJU

Colorado Springs

Fri 1/9

5:11 pm-3:45 pm

2 stops19h 34m

San Juan Luis Munoz Marin Intl

Mon 1/19

6:45 am-9:44 pm

1 stop17h 59m

$365

Colorado SpringsSan Juan

COS - SJU

COSSJU

Colorado Springs

Sat 1/10

5:11 pm-1:35 pm

2 stops17h 24m

San Juan Luis Munoz Marin Intl

Mon 1/19

6:45 am-3:39 pm

1 stop11h 54m

$365

Colorado SpringsSantiago de los Caballeros

COS - STI

COSSTI

Colorado Springs

Wed 9/24

11:01 am-12:27 pm

2 stops23h 26m

Santiago de los Caballeros

Sat 9/27

1:29 pm-10:10 am

2 stops22h 41m

$483

Colorado SpringsPunta Cana

COS - PUJ

COSPUJ

Colorado Springs

Mon 10/13

6:02 am-3:39 pm

1 stop7h 37m

Punta Cana

Mon 10/20

4:23 pm-9:46 am

1 stop19h 23m

$489

Colorado SpringsPunta Cana

COS - PUJ

COSPUJ

Colorado Springs

Fri 9/12

5:55 pm-12:32 pm

2 stops16h 37m

Punta Cana

Sat 9/20

1:57 pm-12:06 pm

2 stops24h 09m

$491

Colorado SpringsPunta Cana

COS - PUJ

COSPUJ

Colorado Springs

Sat 9/20

5:55 pm-12:32 pm

2 stops16h 37m

Punta Cana

Mon 9/29

1:57 pm-12:06 pm

2 stops24h 09m

$491

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/20

Showing 1-10 of 50 results
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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 August 20, 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
4,246 reviews

Overall

8.0

Food

7.0

Boarding

8.1

Crew

8.6

Entertainment

7.5

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.
Southwest
8.0
Very good
4,246 reviews
Southwest
8.0
Very good
4,246 reviews

Overall

8.0

Food

7.0

Boarding

8.1

Crew

8.6

Entertainment

7.5

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.
Delta
8.0
Very good
7,982 reviews
Southwest
8.0
Very good
4,246 reviews

Overall

8.0

Food

7.0

Boarding

8.1

Crew

8.6

Entertainment

7.5

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.
United Airlines
7.4
Good
8,928 reviews
Southwest
8.0
Very good
4,246 reviews

Overall

8.0

Food

7.0

Boarding

8.1

Crew

8.6

Entertainment

7.5

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,246 reviews

Overall

8.0

Food

7.0

Boarding

8.1

Crew

8.6

Entertainment

7.5

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.

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.

  • How long is the flight from Colorado Springs to Caribbean?

    Airlines like United Airlines, American Airlines, and Delta fly from Colorado Springs to Caribbean in about 9h 25m. The time it takes to get you to your destination can typically vary by up to 7h 59m. The distance between Colorado Springs and Caribbean is about 2705 mi. This flight may include one or multiple stops.

  • 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 American Airlines ($123), United Airlines ($168), and Delta ($233).

  • 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 - Bridgetown Grantley Adams Intl 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 August 20, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$192Average$599FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$383Average$724FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$391Average$551FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$430Average$546FlexibilityNo cancel feeOn-time63%

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