HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Caribbean Islands

$157+ 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 11/24. Fares are subject to change and may not be available on all flights or dates of travel.
COS — SJU
Jun 17 — Jun 241
Tue 6/17
Tue 6/24
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Colorado Springs to Caribbean Islands with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

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 June 12, 2025.

Round-trip from

$301
(American Airlines)

One-way from

$157
(American Airlines)

Popular in

December

Cheapest in

September

Average price

$501
From Colorado Springs to Caribbean Islands
Search Deals
One-way flight from Colorado Springs to Caribbean Islands
Search Deals
Highest demand for flights based on searches. 19% potential increase in price ($106 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease ($22 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in June 2025
Search Deals

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 June 12, 2025.

This American Airlines deal was found by Cheapflights users on 6/12. 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 9/265:16 pmCOS - SJU
2 stops19h 37mAmerican Airlines
Sun 9/287:05 pmSJU - COS
2 stops17h 06mAmerican Airlines
Deal found 6/12$301
This United Airlines deal was found by Cheapflights users on 6/9. 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 10/207:00 amCOS - SJU
1 stop8h 30mUnited Airlines
Sat 10/252:00 pmSJU - COS
1 stop9h 54mUnited Airlines
Deal found 6/9$391
This American Airlines deal was found by Cheapflights users on 6/12. 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 10/215:08 pmCOS - MBJ
2 stops18h 47mAmerican Airlines
Tue 10/283:05 pmMBJ - COS
2 stops19h 20mAmerican Airlines
Deal found 6/12$419
This Southwest deal was found by Cheapflights users on 6/12. 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.
Tue 7/111:20 amCOS - SJU
2 stops10h 45mSouthwest
Wed 7/306:30 amSJU - COS
1 stop9h 40mSouthwest
Deal found 6/12$457
This American Airlines deal was found by Cheapflights users on 6/11. 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 7/265:00 amCOS - PUJ
1 stop9h 09mAmerican Airlines
Sat 8/25:10 pmPUJ - COS
1 stop8h 42mAmerican Airlines
Deal found 6/11$487
This American Airlines deal was found by Cheapflights users on 6/11. 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 9/65:16 pmCOS - POP
2 stops17h 20mAmerican Airlines
Sat 9/131:26 pmPOP - COS
2 stops22h 44mAmerican Airlines
Deal found 6/11$493
This Delta deal was found by Cheapflights users on 6/9. 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.
Mon 7/286:00 amCOS - MBJ
1 stop8h 34mDelta
Wed 8/201:20 pmMBJ - COS
1 stop8h 21mDelta
Deal found 6/9$503
This Mytrip deal was found by Cheapflights users on 6/10. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/15:09 pmCOS - SJU
3 stops40h 23mMultiple Airlines
Sat 8/91:37 amSJU - COS
3 stops33h 18mMultiple Airlines
Deal found 6/10$527
This American Airlines deal was found by Cheapflights users on 6/10. 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 12/1612:13 pmCOS - UVF
2 stops21h 47mAmerican Airlines
Tue 12/234:55 pmUVF - COS
2 stops21h 34mAmerican Airlines
Deal found 6/10$556
This Southwest deal was found by Cheapflights users on 6/11. 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 7/314:00 pmCOS - MBJ
2 stops17h 20mSouthwest
Fri 8/112:45 pmMBJ - COS
2 stops11h 30mSouthwest
Deal found 6/11$594
This American Airlines deal was found by Cheapflights users on 6/9. 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 9/215:03 pmCOS - STT
2 stops20h 57mAmerican Airlines
Sun 9/285:10 pmSTT - COS
2 stops19h 01mAmerican Airlines
Deal found 6/9$599
This American Airlines deal was found by Cheapflights users on 6/12. 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 11/95:09 pmCOS - DOM
2 stops18h 21mAmerican Airlines
Sun 11/233:25 pmDOM - COS
2 stops23h 06mAmerican Airlines
Deal found 6/12$605

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 June 12, 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

Fri 9/26

5:16 pm-2:53 pm

2 stops19h 37m

San Juan Luis Munoz Marin Intl

Sun 9/28

7:05 pm-10:11 am

2 stops17h 06m

$301

Colorado SpringsSan Juan

COS - SJU

COSSJU

Colorado Springs

Mon 10/20

7:00 am-5:30 pm

1 stop8h 30m

San Juan Luis Munoz Marin Intl

Fri 10/24

1:05 am-10:40 am

2 stops11h 35m

$391

Colorado SpringsMontego Bay

COS - MBJ

COSMBJ

Colorado Springs

Tue 10/21

5:08 pm-12:55 pm

2 stops18h 47m

Montego Bay Sangster Intl

Tue 10/28

3:05 pm-11:04 am

2 stops20h 59m

$419

Colorado SpringsSan Juan

COS - SJU

COSSJU

Colorado Springs

Tue 7/1

11:20 am-12:05 am

2 stops10h 45m

San Juan Luis Munoz Marin Intl

Wed 7/30

6:30 am-2:10 pm

1 stop9h 40m

$457

Colorado SpringsPunta Cana

COS - PUJ

COSPUJ

Colorado Springs

Sat 7/26

5:00 am-4:09 pm

1 stop9h 09m

Punta Cana

Sat 8/2

5:10 pm-11:52 pm

1 stop8h 42m

$487

Colorado SpringsPuerto Plata

COS - POP

COSPOP

Colorado Springs

Sat 9/6

5:16 pm-12:36 pm

2 stops17h 20m

Puerto Plata La Union

Sat 9/13

1:26 pm-10:10 am

2 stops22h 44m

$493

Colorado SpringsMontego Bay

COS - MBJ

COSMBJ

Colorado Springs

Mon 7/28

6:00 am-3:34 pm

1 stop8h 34m

Montego Bay Sangster Intl

Wed 8/20

1:20 pm-8:41 pm

1 stop8h 21m

$503

Colorado SpringsSan Juan

COS - SJU

COSSJU

Colorado Springs

Fri 8/1

5:09 pm-11:32 am

3 stops40h 23m

San Juan Luis Munoz Marin Intl

Sat 8/9

1:37 am-8:55 am

3 stops33h 18m

$527

Colorado SpringsCastries

COS - UVF

COSUVF

Colorado Springs

Tue 9/9

5:16 pm-2:17 pm

2 stops19h 01m

Castries Hewanorra

Tue 9/16

3:17 pm-10:11 am

2 stops20h 54m

$556

Colorado SpringsMontego Bay

COS - MBJ

COSMBJ

Colorado Springs

Thu 7/31

4:00 pm-10:20 am

2 stops17h 20m

Montego Bay Sangster Intl

Fri 8/1

12:45 pm-11:15 pm

2 stops11h 30m

$594

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/10

Showing 1-10 of 26 results
1
2
3

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.

Rainfall in Caribbean Islands by month

Plan your trip to Caribbean Islands by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Caribbean Islands ranges from 2.2 - 6.1 inches per month. November is typically the wettest month, when rainfall can reach 6.1 in. February is typically the driest time to visit Caribbean Islands when rainfall is around 2.2 in.

Temperature in Caribbean Islands by month

Plan your trip to Caribbean Islands by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Caribbean Islands, use this chart to help with planning. For those seeking warmer temperatures, June is the ideal time of year to visit, when temperatures reach an average of 82.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 77.0 F).

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 June 12, 2025.
Peruse reviews from past customers who have flown with Southwest, Delta and United Airlines from Colorado Springs to Caribbean Islands to help guide your decision. In addition to providing an overall rating, users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,287 reviews

Food

7.1

Overall

8.0

Comfort

8.0

Entertainment

7.6

Boarding

8.2

Crew

8.6

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
4,287 reviews
Southwest
8.0
Very good
4,287 reviews

Food

7.1

Overall

8.0

Comfort

8.0

Entertainment

7.6

Boarding

8.2

Crew

8.6

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
7,950 reviews
Southwest
8.0
Very good
4,287 reviews

Food

7.1

Overall

8.0

Comfort

8.0

Entertainment

7.6

Boarding

8.2

Crew

8.6

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
8,790 reviews
Southwest
8.0
Very good
4,287 reviews

Food

7.1

Overall

8.0

Comfort

8.0

Entertainment

7.6

Boarding

8.2

Crew

8.6

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
4,287 reviews

Food

7.1

Overall

8.0

Comfort

8.0

Entertainment

7.6

Boarding

8.2

Crew

8.6

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 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.

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

    $157 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 $196 and $228, 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 - Castries Hewanorra.

  • 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

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Colorado Springs to Caribbean Islands

See prices for flight routes from nearby airports that may be better suited for you.
Denver to Las Vegas flights
Denver to Seattle flights
Denver to LaGuardia flights
Denver to O'Hare Intl flights
Denver to John F Kennedy Intl flights
Denver to Los Angeles flights
Denver to Orlando flights
Denver to Newark flights
Denver to Cancún flights
Denver to Boston flights
Denver to Dallas/Fort Worth flights
Denver to San Francisco flights
Denver to Miami flights
Denver to San Diego flights
Denver to Honolulu flights
Denver to Philadelphia flights
Denver to Baltimore flights
Denver to Minneapolis flights
Denver to Hobby flights
Denver to Vancouver Intl flights
Denver to Portland flights
Denver to Detroit flights
Denver to Reagan-National flights
Denver to Dulles Intl flights
Denver to Tampa flights
Denver to New Orleans flights
Denver to Ontario flights
Denver to Sky Harbor Intl flights
Denver to Kahului flights
Denver to Santa Ana flights
Denver to Atlanta flights
Denver to George Bush Intcntl flights
Denver to Midway flights
Denver to Fort Lauderdale flights
Denver to Portland flights
Denver to Charlotte flights
Denver to Milwaukee flights
Denver to Grand Rapids flights
Denver to Raleigh flights
Denver to San José del Cabo flights
Denver to Lihue flights
Denver to St. Louis flights
Denver to Cozumel flights
Denver to Nashville flights
Denver to Cleveland flights
Denver to Austin flights
Denver to Anchorage flights
Denver to Traverse City flights
Denver to Sacramento flights
Denver to Madison flights

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 June 12, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$231Average$573FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$362Average$626FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$393Average$548FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$430Average$538FlexibilityNo cancel feeOn-time63%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.