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Caribbean Islands

$168+ 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 3/1. Fares are subject to change and may not be available on all flights or dates of travel.
COS — SJU
Feb 26 — Mar 51
Thu 2/26
Thu 3/5
1 adult, Economy
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Cheap 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 January 27, 2026.

This American Airlines deal was found by Cheapflights users on 1/26. 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 2/281:39 pm
COS
-
SJU
2 stops17h 21m
American Airlines
Wed 3/48:00 am
SJU
-
COS
2 stops10h 58m
American Airlines
Deal found 1/26$272
This American Airlines deal was found by Cheapflights users on 1/25. 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 3/246:00 am
COS
-
SJU
2 stops14h 58m
American Airlines
Wed 4/86:47 am
SJU
-
COS
1 stop18h 43m
American Airlines
Deal found 1/25$340
This Delta deal was found by Cheapflights users on 1/26. 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 2/231:22 pm
COS
-
SJU
1 stop7h 36m
Delta
Mon 3/26:15 am
SJU
-
COS
1 stop9h 10m
Delta
Deal found 1/26$376
This United Airlines deal was found by Cheapflights users on 1/26. 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 5/256:00 am
COS
-
SJU
1 stop9h 30m
United Airlines
Tue 6/21:05 am
SJU
-
COS
2 stops11h 36m
United Airlines
Deal found 1/26$411
This United Airlines deal was found by Cheapflights users on 1/25. 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 2/107:30 am
COS
-
SJU
1 stop10h 56m
United Airlines
Sat 2/147:40 am
SJU
-
COS
2 stops12h 45m
United Airlines
Deal found 1/25$420
This United Airlines deal was found by Cheapflights users on 1/26. 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 5/276:00 am
COS
-
SJU
1 stop9h 30m
United Airlines
Tue 6/21:05 am
SJU
-
COS
2 stops11h 36m
United Airlines
Deal found 1/26$423
This American Airlines deal was found by Cheapflights users on 1/27. 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 11/64:37 pm
COS
-
SJU
2 stops18h 04m
American Airlines
Sat 11/146:44 am
SJU
-
COS
1 stop12h 03m
American Airlines
Deal found 1/27$424
This United Airlines deal was found by Cheapflights users on 1/26. 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 5/266:00 am
COS
-
SJU
1 stop9h 30m
United Airlines
Tue 6/21:05 am
SJU
-
COS
2 stops11h 36m
United Airlines
Deal found 1/26$431
This Delta deal was found by Cheapflights users on 1/26. 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 2/281:22 pm
COS
-
SJU
1 stop7h 36m
Delta
Wed 3/46:15 am
SJU
-
COS
1 stop9h 10m
Delta
Deal found 1/26$433
This Delta deal was found by Cheapflights users on 1/27. 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 3/106:20 am
COS
-
NAS
1 stop8h 25m
Delta
Tue 3/173:05 pm
NAS
-
COS
1 stop7h 23m
Delta
Deal found 1/27$440
This United Airlines deal was found by Cheapflights users on 1/26. 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.
Thu 1/295:50 am
COS
-
SJU
2 stops12h 36m
United Airlines
Thu 2/52:25 pm
SJU
-
COS
1 stop9h 41m
United Airlines
Deal found 1/26$461
This Delta deal was found by Cheapflights users on 1/27. 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 2/281:22 pm
COS
-
NAS
2 stops20h 28m
Delta
Wed 3/41:41 pm
NAS
-
COS
2 stops10h 40m
Delta
Deal found 1/27$469

Find 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 January 27, 2026.

Round-trip from

$272
(American Airlines)

One-way from

$168
(Southwest)

Popular in

December

Cheapest in

August

Average price

$377
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. 9% potential increase in price ($49 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($15 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 2026
Search Deals

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 January 27, 2026.
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

Tue 3/24

6:00 am-10:58 pm

2 stops14h 58m

San Juan Luis Munoz Marin Intl

Wed 4/8

6:47 am-11:30 pm

1 stop18h 43m

$340

Colorado SpringsSan Juan

COS - SJU

COSSJU

Colorado Springs

Mon 5/25

6:00 am-5:30 pm

1 stop9h 30m

San Juan Luis Munoz Marin Intl

Tue 6/2

1:05 am-10:41 am

2 stops11h 36m

$411

Colorado SpringsSan Juan

COS - SJU

COSSJU

Colorado Springs

Tue 2/10

7:30 am-9:26 pm

1 stop10h 56m

San Juan Luis Munoz Marin Intl

Sat 2/14

7:40 am-5:25 pm

2 stops12h 45m

$420

Colorado SpringsSan Juan

COS - SJU

COSSJU

Colorado Springs

Wed 5/27

6:00 am-5:30 pm

1 stop9h 30m

San Juan Luis Munoz Marin Intl

Tue 6/2

1:05 am-10:41 am

2 stops11h 36m

$423

Colorado SpringsSan Juan

COS - SJU

COSSJU

Colorado Springs

Mon 2/23

4:49 pm-11:56 am

2 stops16h 07m

San Juan Luis Munoz Marin Intl

Mon 3/2

4:01 pm-10:10 pm

1 stop9h 09m

$424

Colorado SpringsSan Juan

COS - SJU

COSSJU

Colorado Springs

Sat 2/28

1:22 pm-11:58 pm

1 stop7h 36m

San Juan Luis Munoz Marin Intl

Wed 3/4

6:15 am-12:25 pm

1 stop9h 10m

$433

Colorado SpringsNassau

COS - NAS

COSNAS

Colorado Springs

Tue 3/10

6:20 am-4:45 pm

1 stop8h 25m

Nassau Intl

Tue 3/17

3:05 pm-8:28 pm

1 stop7h 23m

$440

Colorado SpringsNassau

COS - NAS

COSNAS

Colorado Springs

Sat 2/28

1:22 pm-11:50 am

2 stops20h 28m

Nassau Intl

Wed 3/4

1:41 pm-10:21 pm

2 stops10h 40m

$469

Colorado SpringsPunta Cana

COS - PUJ

COSPUJ

Colorado Springs

Sun 3/1

1:39 pm-12:01 pm

2 stops19h 22m

Punta Cana

Wed 3/4

3:46 pm-10:10 pm

1 stop9h 24m

$487

Colorado SpringsPunta Cana

COS - PUJ

COSPUJ

Colorado Springs

Wed 3/11

7:00 am-5:18 pm

1 stop8h 18m

Punta Cana

Wed 3/18

4:20 pm-8:49 am

2 stops18h 29m

$487

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/27

Showing 1-10 of 42 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, April is the cheapest month in which you can book a flight from Colorado Springs to Caribbean Islands (average of $130). Flying from Colorado Springs to Caribbean Islands in December is currently the most expensive (average of $293). 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 January 27, 2026.
Read through reviews of airlines operating flights from Colorado Springs to Caribbean Islands, such as American Airlines. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
American Airlines
7.2
Good
11,197 reviews

Food

6.4

Boarding

7.5

Overall

7.2

Comfort

7.2

Crew

8.0

Entertainment

6.9

Reviews

1 / 20
2.0
Mediocre

Susie,Jan 2026

CLT - TPA

This flight was delayed 3 or 4 times. We had boarded the plane, sat on plane for a good 30 minutes, then we had to board the aircraft, walk to a different gate, wait and then board another aircraft. We arrived in Tampa 4 hours later than the original booking. I feel there should have been some sort of compensation especially for the advantage members.
American Airlines
7.2
Good
11,197 reviews
American Airlines
7.2
Good
11,197 reviews

Food

6.4

Boarding

7.5

Overall

7.2

Comfort

7.2

Crew

8.0

Entertainment

6.9

Reviews

1 / 20
2.0
Mediocre

Susie,Jan 2026

CLT - TPA

This flight was delayed 3 or 4 times. We had boarded the plane, sat on plane for a good 30 minutes, then we had to board the aircraft, walk to a different gate, wait and then board another aircraft. We arrived in Tampa 4 hours later than the original booking. I feel there should have been some sort of compensation especially for the advantage members.

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 30m. Fly via American Airlines, United Airlines, or Southwest 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?

    $132 is the cheapest one-way deal found within the past few days, from United Airlines. You may also be able to find cheap deals on American Airlines and Southwest, with prices starting from $150 and $150, 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 - Punta Cana and Colorado Springs - Nassau 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, April is the cheapest month in which you can book a flight from Colorado Springs to Caribbean Islands (average of $130). Flying from Colorado Springs to Caribbean Islands in December is currently the most expensive (average of $293). 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 January 27, 2026.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$192Average$463FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$266Average$707FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$391Average$588FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$406Average$539FlexibilityNo cancel feeOn-time63%

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