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Caribbean Islands

$123+ Cheap flights from Colorado Springs (COS) to Caribbean Islands

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
août 25 — sept. 11
lun. 8/25
lun. 9/1
1 adult, Economy
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Cheap flight deals from Colorado Springs to Caribbean Islands

Keep the following information in mind while searching for Colorado Springs to Caribbean Islands flight deals. Data was last updated août 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 Islands
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One-way flight from Colorado Springs to Caribbean Islands
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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 Islands

Cheapest flights from Colorado Springs to Caribbean Islands
Explore the most affordable flight options available from Colorado Springs to Caribbean Islands. Find the lowest fares from popular airlines and budget airlines, with prices last updated on août 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.
mar. 10/286:00 amCOS - SJU
1 stop9h 25mUnited Airlines
mar. 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.
mar. 10/285:01 pmCOS - SJU
2 stops17h 38mAmerican Airlines
mar. 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.
sam. 9/67:40 amCOS - SJU
1 stop10h 58mUnited Airlines
ven. 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.
ven. 11/75:17 pmCOS - SJU
2 stops17h 24mAmerican Airlines
lun. 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.
mer. 9/2411:01 amCOS - STI
2 stops23h 26mAmerican Airlines
sam. 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.
lun. 10/136:02 amCOS - PUJ
1 stop7h 37mAmerican Airlines
lun. 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.
ven. 9/125:55 pmCOS - PUJ
2 stops16h 37mDelta
sam. 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.
lun. 9/226:25 pmCOS - MBJ
2 stops16h 18mUnited Airlines
sam. 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.
mar. 10/211:16 pmCOS - MBJ
2 stops21h 07mDelta
mar. 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.
lun. 9/226:02 amCOS - MBJ
1 stop7h 03mAmerican Airlines
sam. 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.
mar. 10/216:02 amCOS - MBJ
1 stop7h 13mAmerican Airlines
mar. 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.
jeu. 10/25:03 pmCOS - MBJ
2 stops19h 35mAmerican Airlines
lun. 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 Islands 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 août 20, 2025.
Use the filters below to find and compare flights from Colorado Springs to Caribbean Islands that are best for you.

Fly from

Colorado Springs

Fly to

Caribbean Islands

Route

Depart

Return

Price

Colorado SpringsSan Juan

COS - SJU

COSSJU

Colorado Springs

mar. 10/28

6:00 am-5:25 pm

1 stop9h 25m

San Juan Luis Munoz Marin Intl

mar. 11/18

8:30 am-5:40 pm

2 stops12h 10m

$245

Colorado SpringsSan Juan

COS - SJU

COSSJU

Colorado Springs

ven. 11/7

5:17 pm-1:41 pm

2 stops17h 24m

San Juan Luis Munoz Marin Intl

lun. 11/10

6:42 pm-11:45 am

2 stops20h 03m

$325

Colorado SpringsSan Juan

COS - SJU

COSSJU

Colorado Springs

mar. 10/28

5:01 pm-12:39 pm

2 stops17h 38m

San Juan Luis Munoz Marin Intl

mar. 11/18

6:42 pm-11:45 am

2 stops20h 03m

$325

Colorado SpringsSan Juan

COS - SJU

COSSJU

Colorado Springs

ven. 1/9

5:11 pm-3:45 pm

2 stops19h 34m

San Juan Luis Munoz Marin Intl

dim. 1/18

6:45 am-9:44 pm

1 stop17h 59m

$365

Colorado SpringsSan Juan

COS - SJU

COSSJU

Colorado Springs

ven. 1/9

5:11 pm-3:45 pm

2 stops19h 34m

San Juan Luis Munoz Marin Intl

lun. 1/19

6:45 am-9:44 pm

1 stop17h 59m

$365

Colorado SpringsSan Juan

COS - SJU

COSSJU

Colorado Springs

sam. 1/10

5:11 pm-1:35 pm

2 stops17h 24m

San Juan Luis Munoz Marin Intl

lun. 1/19

6:45 am-3:39 pm

1 stop11h 54m

$365

Colorado SpringsSantiago de los Caballeros

COS - STI

COSSTI

Colorado Springs

mer. 9/24

11:01 am-12:27 pm

2 stops23h 26m

Santiago de los Caballeros

sam. 9/27

1:29 pm-10:10 am

2 stops22h 41m

$483

Colorado SpringsPunta Cana

COS - PUJ

COSPUJ

Colorado Springs

lun. 10/13

6:02 am-3:39 pm

1 stop7h 37m

Punta Cana

lun. 10/20

4:23 pm-9:46 am

1 stop19h 23m

$489

Colorado SpringsPunta Cana

COS - PUJ

COSPUJ

Colorado Springs

ven. 9/12

5:55 pm-12:32 pm

2 stops16h 37m

Punta Cana

sam. 9/20

1:57 pm-12:06 pm

2 stops24h 09m

$491

Colorado SpringsPunta Cana

COS - PUJ

COSPUJ

Colorado Springs

sam. 9/20

5:55 pm-12:32 pm

2 stops16h 37m

Punta Cana

lun. 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 Islands

Have a flexible travel schedule? Discover the best time to fly to Caribbean Islands 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 Islands

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

Currently, September is the cheapest month in which you can book a flight from Colorado Springs to Caribbean Islands (average of $254). Flying from Colorado Springs to Caribbean Islands 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 Islands

Get insights into the airlines that provide service to Caribbean Islands. 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 Islands. Reviews last updated août 20, 2025.
Read through reviews of airlines operating flights from Colorado Springs to Caribbean Islands, such as Delta, United Airlines, and American Airlines. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
7,982 reviews

Crew

8.5

Comfort

7.9

Entertainment

7.9

Overall

8.0

Food

7.3

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
Delta
8.0
Very good
7,982 reviews
Delta
8.0
Very good
7,982 reviews

Crew

8.5

Comfort

7.9

Entertainment

7.9

Overall

8.0

Food

7.3

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
United Airlines
7.4
Good
8,928 reviews
Delta
8.0
Very good
7,982 reviews

Crew

8.5

Comfort

7.9

Entertainment

7.9

Overall

8.0

Food

7.3

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
American Airlines
7.2
Good
10,000 reviews
Delta
8.0
Very good
7,982 reviews

Crew

8.5

Comfort

7.9

Entertainment

7.9

Overall

8.0

Food

7.3

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!

Related info for your journey

Find useful and relevant information for your journey from Colorado Springs to Caribbean Islands. 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 Islands?

    Most people fly from Colorado Springs (COS) if they book a flight from Colorado Springs to Caribbean Islands. Colorado Springs is conveniently located just 6.7 mi from Colorado Springs’s city center.

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

    There are many flights that can get you from Colorado Springs to Caribbean Islands in 9h 25m. Fly via United Airlines, American Airlines, or Delta to get the fastest option. The distance between Colorado Springs and Caribbean Islands is about 2705 mi. This flight may include one or multiple stops.

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

    $123 is the cheapest one-way deal found within the past few days, from American Airlines. You may also be able to find cheap deals on United Airlines and Delta, with prices starting from $168 and $233, respectively.

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

    The most popular flight routes from Colorado Springs to Caribbean Islands are Colorado Springs - San Juan Luis Munoz Marin Intl, Colorado Springs - Montego Bay Sangster Intl and Colorado Springs - Bridgetown Grantley Adams Intl.

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

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

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

    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 Islands.

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

    Yes. Cheapflights offers flight deals from Colorado Springs to Caribbean Islands 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 Islands?

    Currently, September is the cheapest month in which you can book a flight from Colorado Springs to Caribbean Islands (average of $254). Flying from Colorado Springs to Caribbean Islands 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 Islands

Discover the top 4 airlines that operate flights from Colorado Springs to Caribbean Islands. 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 août 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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