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$205+ 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 1/5. Fares are subject to change and may not be available on all flights or dates of travel.
COS — SJU
Dec 21 — Dec 281
Sun 12/21
Sun 12/28
1 adult, Economy
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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 November 21, 2025.

This American Airlines deal was found by Cheapflights users on 11/21. 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 12/812:45 pmCOS - SJU
2 stops18h 24mAmerican Airlines
Mon 12/155:10 pmSJU - COS
2 stops19h 37mAmerican Airlines
Deal found 11/21$324
This American Airlines deal was found by Cheapflights users on 11/20. 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 12/512:45 pmCOS - SJU
2 stops18h 24mAmerican Airlines
Tue 12/96:00 amSJU - COS
2 stops14h 35mAmerican Airlines
Deal found 11/20$383
This American Airlines deal was found by Cheapflights users on 11/20. 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 12/512:45 pmCOS - SJU
2 stops18h 24mAmerican Airlines
Mon 12/85:10 pmSJU - COS
2 stops19h 44mAmerican Airlines
Deal found 11/20$407
This American Airlines deal was found by Cheapflights users on 11/19. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/812:45 pmCOS - SJU
2 stops18h 24mAmerican Airlines
Tue 12/166:00 amSJU - COS
2 stops14h 35mAmerican Airlines
Deal found 11/19$412
This American Airlines deal was found by Cheapflights users on 11/20. 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.
Mon 12/1512:45 pmCOS - SJU
2 stops18h 24mAmerican Airlines
Mon 12/221:30 amSJU - COS
1 stop11h 35mAmerican Airlines
Deal found 11/20$458
This American Airlines deal was found by Cheapflights users on 11/20. 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 11/2510:27 amCOS - SJU
1 stop16h 43mAmerican Airlines
Tue 12/26:42 pmSJU - COS
2 stops18h 05mAmerican Airlines
Deal found 11/20$460
This American Airlines deal was found by Cheapflights users on 11/19. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/65:33 amCOS - SJU
1 stop12h 52mAmerican Airlines
Mon 12/157:00 amSJU - COS
1 stop13h 35mAmerican Airlines
Deal found 11/19$500
This Delta deal was found by Cheapflights users on 11/19. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/206:02 pmCOS - SJU
2 stops15h 54mDelta
Thu 11/273:32 pmSJU - COS
1 stop8h 08mDelta
Deal found 11/19$559
This United Airlines deal was found by Cheapflights users on 11/19. 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.
Wed 11/197:45 amCOS - SJU
2 stops10h 15mUnited Airlines
Fri 12/122:05 amSJU - COS
2 stops15h 24mUnited Airlines
Deal found 11/19$574
This United Airlines deal was found by Cheapflights users on 11/20. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/57:45 amCOS - SJU
2 stops11h 37mUnited Airlines
Sun 12/72:05 amSJU - COS
2 stops13h 16mUnited Airlines
Deal found 11/20$583
This American Airlines deal was found by Cheapflights users on 11/20. 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.
Sun 12/214:46 pmCOS - GCM
2 stops17h 11mAmerican Airlines
Fri 12/264:30 pmGCM - COS
1 stop9h 17mAmerican Airlines
Deal found 11/20$677
This American Airlines deal was found by Cheapflights users on 11/19. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/256:00 amCOS - NAS
1 stop6h 10mAmerican Airlines
Mon 12/293:10 pmNAS - COS
1 stop7h 21mAmerican Airlines
Deal found 11/19$690

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 November 21, 2025.

Round-trip from

$324
(American Airlines)

One-way from

$205
(American Airlines)

Popular in

December

Cheapest in

August

Average price

$576
From Colorado Springs to Caribbean
Search Deals
One-way flight from Colorado Springs to Caribbean
Search Deals
Highest demand for flights based on searches. 16% potential increase in price ($96 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($18 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in November 2025
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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 November 21, 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

Mon 12/8

12:45 pm-10:09 am

2 stops18h 24m

San Juan Luis Munoz Marin Intl

Tue 12/16

6:00 am-5:35 pm

2 stops14h 35m

$324

Colorado SpringsSan Juan

COS - SJU

COSSJU

Colorado Springs

Mon 12/8

4:59 pm-10:09 am

2 stops14h 10m

San Juan Luis Munoz Marin Intl

Mon 12/15

7:00 am-5:35 pm

1 stop13h 35m

$324

Colorado SpringsSan Juan

COS - SJU

COSSJU

Colorado Springs

Mon 1/26

3:17 pm-12:27 pm

2 stops18h 10m

San Juan Luis Munoz Marin Intl

Thu 1/29

6:00 am-2:09 pm

2 stops11h 09m

$337

Colorado SpringsSan Juan

COS - SJU

COSSJU

Colorado Springs

Thu 1/8

3:17 pm-1:38 pm

2 stops19h 21m

San Juan Luis Munoz Marin Intl

Fri 2/20

10:57 am-11:54 pm

2 stops15h 57m

$348

Colorado SpringsSanto Domingo

COS - SDQ

COSSDQ

Colorado Springs

Wed 1/14

10:21 am-12:21 pm

2 stops23h 00m

Santo Domingo Las Americas

Tue 1/20

1:23 pm-9:51 am

2 stops23h 28m

$454

Colorado SpringsPunta Cana

COS - PUJ

COSPUJ

Colorado Springs

Sun 3/1

4:53 pm-3:46 pm

2 stops19h 53m

Punta Cana

Wed 3/4

3:59 pm-10:10 pm

1 stop9h 11m

$466

Colorado SpringsSanto Domingo

COS - SDQ

COSSDQ

Colorado Springs

Tue 3/3

10:34 am-10:02 am

2 stops20h 28m

Santo Domingo Las Americas

Fri 3/6

11:02 am-12:52 pm

2 stops28h 50m

$472

Colorado SpringsPuerto Plata

COS - POP

COSPOP

Colorado Springs

Mon 2/2

3:17 pm-3:42 pm

2 stops21h 25m

Puerto Plata La Union

Fri 2/6

3:32 pm-1:57 pm

2 stops25h 25m

$472

Colorado SpringsWillemstad

COS - CUR

COSCUR

Colorado Springs

Fri 1/9

3:17 pm-2:05 pm

2 stops19h 48m

Willemstad Hato Int.

Sat 1/17

5:49 pm-2:09 pm

2 stops23h 20m

$500

Colorado SpringsGeorge Town

COS - GCM

COSGCM

Colorado Springs

Sat 2/21

12:22 pm-2:30 pm

1 stop24h 08m

George Town Owen Roberts Intl

Tue 3/3

4:30 pm-10:10 pm

1 stop7h 40m

$500

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/19

Showing 1-10 of 38 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, April is the cheapest month in which you can book a flight from Colorado Springs to Caribbean (average of $130). Flying from Colorado Springs to Caribbean in June is currently the most expensive (average of $273). 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 November 21, 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
4,251 reviews

Food

7.0

Boarding

8.1

Overall

8.0

Crew

8.6

Comfort

8.0

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Southwest
8.0
Very good
4,251 reviews
Southwest
8.0
Very good
4,251 reviews

Food

7.0

Boarding

8.1

Overall

8.0

Crew

8.6

Comfort

8.0

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Delta
7.9
Good
8,002 reviews
Southwest
8.0
Very good
4,251 reviews

Food

7.0

Boarding

8.1

Overall

8.0

Crew

8.6

Comfort

8.0

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
United Airlines
7.4
Good
9,028 reviews
Southwest
8.0
Very good
4,251 reviews

Food

7.0

Boarding

8.1

Overall

8.0

Crew

8.6

Comfort

8.0

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
American Airlines
7.2
Good
11,047 reviews
Southwest
8.0
Very good
4,251 reviews

Food

7.0

Boarding

8.1

Overall

8.0

Crew

8.6

Comfort

8.0

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines

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 American Airlines, Delta, and United Airlines fly from Colorado Springs to Caribbean in about 7h 14m. The time it takes to get you to your destination can typically vary by up to 18h. The distance between Colorado Springs and Caribbean is about 1847 mi. This flight may include one or multiple stops.

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

    Most travelers choose Colorado Springs - San Juan Luis Munoz Marin Intl, Colorado Springs - Punta Cana or Colorado Springs - Montego Bay Sangster 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, April is the cheapest month in which you can book a flight from Colorado Springs to Caribbean (average of $130). Flying from Colorado Springs to Caribbean in June is currently the most expensive (average of $273). 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 November 21, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$192Average$526FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$350Average$740FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$391Average$608FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$430Average$540FlexibilityNo cancel feeOn-time63%

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