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$188+ 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 10/20. Fares are subject to change and may not be available on all flights or dates of travel.
COS — SJU
Oct 17 — Oct 241
Fri 10/17
Fri 10/24
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 September 17, 2025.

Round-trip from

$265
(American Airlines)

One-way from

$188
(Delta)

Popular in

December

Cheapest in

August

Average price

$423
From Colorado Springs to Caribbean
Search Deals
One-way flight from Colorado Springs to Caribbean
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Highest demand for flights based on searches. 17% potential increase in price ($97 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($20 potential savings vs. average RT price).
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Average for round-trip flights in September 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 September 17, 2025.

This American Airlines deal was found by Cheapflights users on 9/14. 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 10/255:01 pmCOS - SJU
2 stops16h 05mAmerican Airlines
Thu 10/307:05 amSJU - COS
2 stops18h 39mAmerican Airlines
Deal found 9/14$265
This United Airlines deal was found by Cheapflights users on 9/14. 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 10/2510:30 amCOS - SJU
2 stops11h 27mUnited Airlines
Thu 10/301:25 pmSJU - COS
1 stop10h 34mUnited Airlines
Deal found 9/14$304
This American Airlines deal was found by Cheapflights users on 9/16. 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 12/54:59 pmCOS - SJU
2 stops17h 31mAmerican Airlines
Tue 12/96:00 amSJU - COS
2 stops12h 45mAmerican Airlines
Deal found 9/16$350
This Southwest deal was found by Cheapflights users on 9/16. 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.
Thu 11/66:00 amCOS - SJU
2 stops13h 20mSouthwest
Fri 11/148:45 pmSJU - COS
2 stops16h 15mSouthwest
Deal found 9/16$400
This Kiwi.com deal was found by Cheapflights users on 9/15. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/1310:31 amCOS - SJU
2 stops35h 58mMultiple Airlines
Thu 10/164:16 pmSJU - COS
1 stop18h 24mMultiple Airlines
Deal found 9/15$454
This American Airlines deal was found by Cheapflights users on 9/15. 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 11/145:17 pmCOS - SJU
2 stops17h 26mAmerican Airlines
Tue 11/257:15 amSJU - COS
1 stop19h 33mAmerican Airlines
Deal found 9/15$460
This Kiwi.com deal was found by Cheapflights users on 9/15. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/179:30 amCOS - SJU
1 stop31h 28mMultiple Airlines
Sun 10/195:54 pmSJU - COS
1 stop17h 47mMultiple Airlines
Deal found 9/15$462
This Southwest deal was found by Cheapflights users on 9/17. 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.
Mon 10/1311:10 amCOS - SJU
1 stop11h 35mSouthwest
Thu 11/66:40 amSJU - COS
2 stops12h 55mSouthwest
Deal found 9/17$485
This Delta deal was found by Cheapflights users on 9/16. 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.
Sat 10/256:00 amCOS - MBJ
1 stop8h 34mDelta
Fri 10/311:32 pmMBJ - COS
1 stop7h 58mDelta
Deal found 9/16$503
This American Airlines deal was found by Cheapflights users on 9/15. 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 10/215:01 pmCOS - MBJ
2 stops19h 04mAmerican Airlines
Tue 10/282:30 pmMBJ - COS
2 stops20h 16mAmerican Airlines
Deal found 9/15$507
This American Airlines deal was found by Cheapflights users on 9/14. 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 11/212:36 pmCOS - PUJ
1 stop24h 51mAmerican Airlines
Sat 11/85:30 pmPUJ - COS
2 stops19h 24mAmerican Airlines
Deal found 9/14$529
This United Airlines deal was found by Cheapflights users on 9/16. 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 12/57:00 amCOS - SJU
1 stop8h 25mUnited Airlines
Tue 12/92:25 pmSJU - COS
1 stop10h 34mUnited Airlines
Deal found 9/16$542

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 September 17, 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 3/10

5:08 pm-3:55 am

1 stop8h 47m

San Juan Luis Munoz Marin Intl

Wed 3/11

3:45 pm-11:30 am

2 stops21h 45m

$337

Colorado SpringsSan Juan

COS - SJU

COSSJU

Colorado Springs

Tue 3/10

7:30 am-5:25 pm

1 stop7h 55m

San Juan Luis Munoz Marin Intl

Tue 3/10

1:05 am-11:18 am

2 stops12h 13m

$427

Colorado SpringsSan Juan

COS - SJU

COSSJU

Colorado Springs

Mon 10/13

10:31 am-12:29 am

2 stops35h 58m

San Juan Luis Munoz Marin Intl

Thu 10/16

4:16 pm-8:40 am

1 stop18h 24m

$454

Colorado SpringsSan Juan

COS - SJU

COSSJU

Colorado Springs

Sat 2/21

6:05 am-6:45 pm

2 stops9h 40m

San Juan Luis Munoz Marin Intl

Sat 2/28

2:10 pm-9:30 pm

2 stops10h 20m

$462

Colorado SpringsSan Juan

COS - SJU

COSSJU

Colorado Springs

Sat 10/25

10:30 am-11:57 pm

2 stops11h 27m

San Juan Luis Munoz Marin Intl

Wed 10/29

1:05 am-10:53 am

2 stops11h 48m

$466

Colorado SpringsPunta Cana

COS - PUJ

COSPUJ

Colorado Springs

Sun 3/1

5:06 pm-3:50 pm

2 stops19h 44m

Punta Cana

Wed 3/4

2:10 pm-8:13 pm

1 stop9h 03m

$466

Colorado SpringsPunta Cana

COS - PUJ

COSPUJ

Colorado Springs

Thu 2/26

5:06 pm-3:30 pm

2 stops19h 24m

Punta Cana

Fri 3/6

6:10 pm-11:30 am

2 stops20h 20m

$466

Colorado SpringsSan Juan

COS - SJU

COSSJU

Colorado Springs

Mon 10/13

11:10 am-12:45 am

1 stop11h 35m

San Juan Luis Munoz Marin Intl

Thu 11/6

6:40 am-4:35 pm

2 stops12h 55m

$485

Colorado SpringsWillemstad

COS - CUR

COSCUR

Colorado Springs

Fri 1/9

5:11 pm-4:10 pm

2 stops19h 59m

Willemstad Hato Int.

Sat 1/17

3:35 pm-11:30 am

2 stops22h 55m

$500

Colorado SpringsMontego Bay

COS - MBJ

COSMBJ

Colorado Springs

Sat 10/25

6:20 pm-1:05 pm

2 stops17h 45m

Montego Bay Sangster Intl

Fri 10/31

1:48 pm-9:47 pm

1 stop8h 59m

$503

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/16

Showing 1-10 of 43 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 September 17, 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
4,242 reviews

Entertainment

7.5

Overall

8.0

Boarding

8.1

Comfort

8.0

Crew

8.6

Food

7.0

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
4,242 reviews
Southwest
8.0
Very good
4,242 reviews

Entertainment

7.5

Overall

8.0

Boarding

8.1

Comfort

8.0

Crew

8.6

Food

7.0

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
8.0
Very good
7,961 reviews
Southwest
8.0
Very good
4,242 reviews

Entertainment

7.5

Overall

8.0

Boarding

8.1

Comfort

8.0

Crew

8.6

Food

7.0

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
8,926 reviews
Southwest
8.0
Very good
4,242 reviews

Entertainment

7.5

Overall

8.0

Boarding

8.1

Comfort

8.0

Crew

8.6

Food

7.0

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
10,000 reviews
Southwest
8.0
Very good
4,242 reviews

Entertainment

7.5

Overall

8.0

Boarding

8.1

Comfort

8.0

Crew

8.6

Food

7.0

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, United Airlines, and Delta fly from Colorado Springs to Caribbean in about 7h 55m. The time it takes to get you to your destination can typically vary by up to 12h 09m. 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 Delta ($188), United Airlines ($228), and Southwest ($232).

  • 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 September 17, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$192Average$583FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$383Average$754FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$391Average$562FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$430Average$543FlexibilityNo cancel feeOn-time63%

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