$216+ Cheap flights from Colorado Springs (COS) to Caribbean
This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 12/15. Fares are subject to change and may not be available on all flights or dates of travel.
COS — SJU
Nov 14 — Nov 211
Round-trip
1 adult, Economy
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Find cheap flights from Colorado Springs to Caribbean 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
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Cheapest flights from Colorado Springs to CaribbeanExplore 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 October 15, 2026.
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 October 15, 2026.
This American Airlines deal was found by Cheapflights users on 10/13. 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 11/175:17 pm -
2 stops18h 02m
Wed 12/212:59 pm -
2 stops13h 02m
Deal found 10/13![American Airlines logo]()
$432
This American Airlines deal was found by Cheapflights users on 10/11. 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.
Tue 11/2412:56 pm -
1 stop8h 17m
Tue 12/86:28 am -
1 stop8h 41m
Deal found 10/11![American Airlines logo]()
$482
This Southwest deal was found by Cheapflights users on 10/12. 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.
Sun 12/610:15 am -
2 stops11h 50m
Sun 12/136:35 am -
2 stops12h 55m
Deal found 10/12![Southwest logo]()
$534
This United Airlines deal was found by Cheapflights users on 10/11. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/266:00 am -
1 stop9h 25m
Fri 10/3012:00 pm -
2 stops12h 03m
Deal found 10/11![United Airlines logo]()
$544
This American Airlines deal was found by Cheapflights users on 10/12. 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 12/68:00 am -
1 stop13h 09m
Sun 12/136:28 am -
1 stop19h 33m
Deal found 10/12![American Airlines logo]()
$547
This American Airlines deal was found by Cheapflights users on 10/13. 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.
Wed 10/281:26 pm -
2 stops18h 20m
Sun 11/16:28 am -
1 stop8h 36m
Deal found 10/13![American Airlines logo]()
$549
This American Airlines deal was found by Cheapflights users on 10/14. 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.
Mon 11/28:00 am -
1 stop7h 09m
Wed 11/111:21 pm -
1 stop11h 40m
Deal found 10/14![American Airlines logo]()
$553
This Southwest deal was found by Cheapflights users on 10/14. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/1311:00 am -
2 stops11h 00m
Thu 11/268:40 am -
2 stops10h 40m
Deal found 10/14![Southwest logo]()
$554
This American Airlines deal was found by Cheapflights users on 10/15. 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.
Sun 11/298:00 am -
1 stop7h 09m
Sun 12/66:12 pm -
2 stops19h 57m
Deal found 10/15![American Airlines logo]()
$562
This Southwest deal was found by Cheapflights users on 10/15. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/3010:10 am -
2 stops12h 00m
Tue 11/36:10 am -
2 stops12h 25m
Deal found 10/15![Southwest logo]()
$564
This United Airlines deal was found by Cheapflights users on 10/13. 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 12/15:05 pm -
2 stops18h 28m
Sun 12/62:40 pm -
1 stop8h 57m
Deal found 10/13![United Airlines logo]()
$564
This United Airlines deal was found by Cheapflights users on 10/13. 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 11/75:05 pm -
2 stops16h 44m
Thu 11/122:40 pm -
1 stop9h 05m
Deal found 10/13![United Airlines logo]()
$565
Best flights from Colorado Springs to CaribbeanDiscover carefully curated flight deals from Colorado Springs to Caribbean that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated October 15, 2026.
Discover carefully curated flight deals from Colorado Springs to Caribbean that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated October 15, 2026.
This American Airlines deal was found by Cheapflights users on 10/10. 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.
Fri 1/812:58 pm -
2 stops17h 40m
Sat 1/167:22 am -
2 stops14h 18m
Deal found 10/10![American Airlines logo]()
$432
This United Airlines deal was found by Cheapflights users on 10/14. 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.
Mon 2/15:45 am -
1 stop9h 40m
Wed 2/103:46 pm -
1 stop9h 05m
Deal found 10/14![United Airlines logo]()
$432
This Delta deal was found by Cheapflights users on 10/14. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 1/181:40 pm -
1 stop7h 10m
Sun 1/246:15 am -
1 stop9h 43m
Deal found 10/14![Delta logo]()
$488
This Southwest deal was found by Cheapflights users on 10/11. 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.
Fri 12/1110:15 am -
2 stops11h 40m
Sat 12/194:15 pm -
2 stops9h 25m
Deal found 10/11![Southwest logo]()
$534
This American Airlines deal was found by Cheapflights users on 10/10. 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.
Thu 3/42:21 pm -
1 stop8h 26m
Tue 3/236:15 am -
1 stop8h 19m
Deal found 10/10![American Airlines logo]()
$475
This American Airlines deal was found by Cheapflights users on 10/13. 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 11/2412:56 pm -
1 stop8h 17m
Tue 12/86:28 am -
1 stop8h 41m
Deal found 10/13![American Airlines logo]()
$482
This United Airlines deal was found by Cheapflights users on 10/14. 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.
Tue 1/121:30 pm -
2 stops20h 43m
Tue 1/262:54 pm -
1 stop9h 05m
Deal found 10/14![United Airlines logo]()
$534
This Delta deal was found by Cheapflights users on 10/12. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/251:40 pm -
1 stop7h 39m
Mon 3/296:15 am -
2 stops12h 59m
Deal found 10/12![Delta logo]()
$540
This United Airlines deal was found by Cheapflights users on 10/11. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/266:00 am -
1 stop9h 25m
Fri 10/3012:00 pm -
2 stops12h 03m
Deal found 10/11![United Airlines logo]()
$544
This Delta deal was found by Cheapflights users on 10/11. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/66:00 am -
1 stop5h 54m
Tue 11/103:15 pm -
1 stop7h 35m
Deal found 10/11![Delta logo]()
$566
This American Airlines deal was found by Cheapflights users on 10/14. 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.
Tue 1/123:11 pm -
2 stops20h 57m
Tue 1/261:03 pm -
2 stops23h 03m
Deal found 10/14![American Airlines logo]()
$538
This United Airlines deal was found by Cheapflights users on 10/12. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/276:00 am -
1 stop9h 25m
Sat 10/311:21 pm -
1 stop10h 01m
Deal found 10/12![United Airlines logo]()
$544
This American Airlines deal was found by Cheapflights users on 10/11. 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.
Mon 10/268:01 am -
1 stop13h 19m
Fri 10/306:00 am -
1 stop11h 00m
Deal found 10/11![American Airlines logo]()
$544
This United Airlines deal was found by Cheapflights users on 10/13. 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 12/16:20 pm -
2 stops17h 28m
Mon 12/72:40 pm -
1 stop8h 57m
Deal found 10/13![United Airlines logo]()
$564
This American Airlines deal was found by Cheapflights users on 10/14. 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.
Mon 11/28:00 am -
1 stop7h 09m
Wed 11/111:21 pm -
1 stop11h 40m
Deal found 10/14![American Airlines logo]()
$553
This United Airlines deal was found by Cheapflights users on 10/13. 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 12/15:05 pm -
2 stops18h 28m
Sun 12/62:40 pm -
1 stop8h 57m
Deal found 10/13![United Airlines logo]()
$564
This American Airlines deal was found by Cheapflights users on 10/15. 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.
Sun 11/298:00 am -
1 stop7h 09m
Sun 12/66:12 pm -
2 stops19h 57m
Deal found 10/15![American Airlines logo]()
$562
This United Airlines deal was found by Cheapflights users on 10/13. 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 12/15:05 pm -
2 stops16h 44m
Tue 12/82:40 pm -
2 stops9h 23m
Deal found 10/13![United Airlines logo]()
$569
This American Airlines deal was found by Cheapflights users on 10/15. 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 10/303:58 pm -
2 stops17h 33m
Tue 11/36:28 am -
1 stop15h 06m
Deal found 10/15![American Airlines logo]()
$564
This United Airlines deal was found by Cheapflights users on 10/10. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/246:25 pm -
2 stops17h 08m
Tue 12/12:40 pm -
2 stops9h 23m
Deal found 10/10![United Airlines logo]()
$569
This American Airlines deal was found by Cheapflights users on 10/12. 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 11/65:17 pm -
2 stops18h 01m
Tue 11/1010:20 am -
2 stops14h 26m
Deal found 10/12![American Airlines logo]()
$571
This United Airlines deal was found by Cheapflights users on 10/12. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/2612:05 pm -
1 stop23h 28m
Thu 12/312:55 pm -
2 stops10h 27m
Deal found 10/12![United Airlines logo]()
$580
This American Airlines deal was found by Cheapflights users on 10/15. 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.
Wed 11/115:17 pm -
2 stops19h 11m
Wed 11/181:21 pm -
1 stop11h 40m
Deal found 10/15![American Airlines logo]()
$585
This United Airlines deal was found by Cheapflights users on 10/12. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/126:20 pm -
2 stops18h 19m
Sat 12/192:00 pm -
1 stop8h 47m
Deal found 10/12![United Airlines logo]()
$637
This American Airlines deal was found by Cheapflights users on 10/14. 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.
Tue 11/178:00 am -
1 stop7h 09m
Sun 11/226:09 pm -
2 stops21h 15m
Deal found 10/14![American Airlines logo]()
$615
This United Airlines deal was found by Cheapflights users on 10/12. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/267:35 am -
1 stop6h 55m
Thu 12/35:45 pm -
2 stops18h 49m
Deal found 10/12![United Airlines logo]()
$654
This American Airlines deal was found by Cheapflights users on 10/13. 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 2/205:31 pm -
2 stops20h 11m
Sat 2/275:42 pm -
2 stops23h 09m
Deal found 10/13![American Airlines logo]()
$630
This United Airlines deal was found by Cheapflights users on 10/13. 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 2/175:13 pm -
2 stops15h 32m
Thu 2/252:15 pm -
1 stop10h 09m
Deal found 10/13![United Airlines logo]()
$662
This American Airlines deal was found by Cheapflights users on 10/11. 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.
Fri 3/55:31 pm -
2 stops20h 07m
Fri 3/125:39 pm -
2 stops23h 12m
Deal found 10/11![American Airlines logo]()
$646
This United Airlines deal was found by Cheapflights users on 10/12. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/296:25 pm -
2 stops16h 15m
Tue 11/32:50 pm -
2 stops22h 43m
Deal found 10/12![United Airlines logo]()
$720
Last-minute flights from Colorado Springs to CaribbeanDiscover last-minute flight deals from Colorado Springs to Caribbean. Data last updated October 15, 2026 and is based on user searches.
Discover last-minute flight deals from Colorado Springs to Caribbean. Data last updated October 15, 2026 and is based on user searches.
This United Airlines deal was found by Cheapflights users on 10/11. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/266:00 am -
1 stop9h 25m
Fri 10/3012:00 pm -
2 stops12h 03m
Deal found 10/11![United Airlines logo]()
$544
This American Airlines deal was found by Cheapflights users on 10/13. 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.
Wed 10/281:26 pm -
2 stops18h 20m
Sun 11/16:28 am -
1 stop8h 36m
Deal found 10/13![American Airlines logo]()
$549
This United Airlines deal was found by Cheapflights users on 10/15. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/305:30 am -
1 stop9h 55m
Tue 11/32:21 pm -
1 stop10h 01m
Deal found 10/15![United Airlines logo]()
$564
This American Airlines deal was found by Cheapflights users on 10/14. 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.
Mon 11/28:00 am -
1 stop7h 09m
Wed 11/111:21 pm -
1 stop11h 40m
Deal found 10/14![American Airlines logo]()
$553
This Delta deal was found by Cheapflights users on 10/13. 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.
Fri 11/66:00 am -
1 stop5h 54m
Tue 11/101:18 pm -
1 stop9h 32m
Deal found 10/13![Delta logo]()
$566
This American Airlines deal was found by Cheapflights users on 10/11. 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.
Fri 11/65:17 pm -
2 stops18h 01m
Tue 11/1010:20 am -
2 stops14h 26m
Deal found 10/11![American Airlines logo]()
$571
This United Airlines deal was found by Cheapflights users on 10/13. 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 11/75:05 pm -
2 stops16h 44m
Thu 11/122:40 pm -
1 stop9h 05m
Deal found 10/13![United Airlines logo]()
$565
This Southwest deal was found by Cheapflights users on 10/14. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/1311:00 am -
2 stops11h 00m
Thu 11/268:40 am -
2 stops10h 40m
Deal found 10/14![Southwest logo]()
$554
This American Airlines deal was found by Cheapflights users on 10/13. 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 11/175:17 pm -
2 stops18h 02m
Wed 12/212:59 pm -
2 stops13h 02m
Deal found 10/13![American Airlines logo]()
$432
This American Airlines deal was found by Cheapflights users on 10/11. 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.
Tue 11/2412:56 pm -
1 stop8h 17m
Tue 12/86:28 am -
1 stop8h 41m
Deal found 10/11![American Airlines logo]()
$482
This United Airlines deal was found by Cheapflights users on 10/10. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/246:25 pm -
2 stops17h 08m
Tue 12/12:40 pm -
2 stops9h 23m
Deal found 10/10![United Airlines logo]()
$569
This American Airlines deal was found by Cheapflights users on 10/15. 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.
Sun 11/298:00 am -
1 stop7h 09m
Sun 12/66:12 pm -
2 stops19h 57m
Deal found 10/15![American Airlines logo]()
$562
One-way flights from Colorado Springs to CaribbeanSearch for one-way flight options from Colorado Springs to Caribbean. Find affordable one-way fares based on user searches. Data last updated October 15, 2026.
Search for one-way flight options from Colorado Springs to Caribbean. Find affordable one-way fares based on user searches. Data last updated October 15, 2026.
This American Airlines deal was found by Cheapflights users on 10/10. 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 12/151:39 pm -
2 stops18h 05m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/10![American Airlines logo]()
$216
This American Airlines deal was found by Cheapflights users on 10/13. 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.
Wed 12/161:39 pm -
2 stops16h 57m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/13![American Airlines logo]()
$221
This American Airlines deal was found by Cheapflights users on 10/11. 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 1/912:58 pm -
2 stops17h 40m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/11![American Airlines logo]()
$224
This American Airlines deal was found by Cheapflights users on 10/11. 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.
Wed 11/41:34 pm -
2 stops17h 56m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/11![American Airlines logo]()
$234
This United Airlines deal was found by Cheapflights users on 10/12. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/145:05 pm -
2 stops19h 34m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/12![United Airlines logo]()
$242
This American Airlines deal was found by Cheapflights users on 10/11. 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.
Thu 11/1912:56 pm -
2 stops17h 42m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/11![American Airlines logo]()
$266
This United Airlines deal was found by Cheapflights users on 10/12. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/278:40 am -
2 stops12h 56m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/12![United Airlines logo]()
$272
This Kiwi.com deal was found by Cheapflights users on 10/14. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/296:00 pm -
3 stops50h 17m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/14![Multiple Airlines logo]()
$290
This Delta deal was found by Cheapflights users on 10/14. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/206:00 am -
1 stop8h 49m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/14![Delta logo]()
$311
This United Airlines deal was found by Cheapflights users on 10/12. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/47:35 am -
1 stop27h 58m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/12![United Airlines logo]()
$313
This United Airlines deal was found by Cheapflights users on 10/14. 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.
Wed 12/168:38 am -
2 stops12h 58m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/14![United Airlines logo]()
$316
Find 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 October 15, 2026.
Round-trip from | $432 (American Airlines) |
|---|---|
One-way from | $216 (American Airlines) |
Popular in | December |
Cheapest in | October |
Average price | $420 |
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 7,457,451 searches. Data last updated October 15, 2026.
Use the filters below to find and compare flights from Colorado Springs to Caribbean that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
Colorado SpringsSan Juan
COS Colorado Springs - SJU San Juan Luis Munoz Marin Intl
COSSJU
Colorado Springs
Wed 2/24
9:10 am-10:00 pm
2 stops9h 50m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-9:00 pm
Nonstop0h 00m
$216
Colorado SpringsSan Juan
COS Colorado Springs - SJU San Juan Luis Munoz Marin Intl
COSSJU
Colorado Springs
Sat 1/9
12:58 pm-9:38 am
2 stops17h 40m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-9:00 pm
Nonstop0h 00m
$224
Colorado SpringsNassau
COS Colorado Springs - NAS Nassau Intl
COSNAS
Colorado Springs
Wed 11/4
1:34 pm-9:30 am
2 stops17h 56m
Nassau Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$234
Colorado SpringsSan Juan
COS Colorado Springs - SJU San Juan Luis Munoz Marin Intl
COSSJU
Colorado Springs
Tue 12/15
1:39 pm-10:44 am
2 stops18h 05m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-9:00 pm
Nonstop0h 00m
$236
Colorado SpringsMontego Bay
COS Colorado Springs - MBJ Montego Bay Sangster Intl
COSMBJ
Colorado Springs
Sat 11/14
5:05 pm-2:39 pm
2 stops19h 34m
Montego Bay Sangster Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$242
Colorado SpringsMontego Bay
COS Colorado Springs - MBJ Montego Bay Sangster Intl
COSMBJ
Colorado Springs
Sat 11/14
6:00 am-4:57 pm
1 stop8h 57m
Montego Bay Sangster Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$242
Colorado SpringsSan Juan
COS Colorado Springs - SJU San Juan Luis Munoz Marin Intl
COSSJU
Colorado Springs
Thu 11/19
12:56 pm-12:13 am
1 stop8h 17m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-9:00 pm
Nonstop0h 00m
$266
Colorado SpringsSan Juan
COS Colorado Springs - SJU San Juan Luis Munoz Marin Intl
COSSJU
Colorado Springs
Tue 10/27
6:00 am-4:49 pm
1 stop8h 49m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-9:00 pm
Nonstop0h 00m
$272
Colorado SpringsSan Juan
COS Colorado Springs - SJU San Juan Luis Munoz Marin Intl
COSSJU
Colorado Springs
Tue 10/27
8:40 am-11:36 pm
2 stops12h 56m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-9:00 pm
Nonstop0h 00m
$272
Colorado SpringsSan Juan
COS Colorado Springs - SJU San Juan Luis Munoz Marin Intl
COSSJU
Colorado Springs
Thu 10/29
1:26 pm-9:46 am
2 stops18h 20m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-9:00 pm
Nonstop0h 00m
$272
Showing 1-10 of 44 resultsSorted by cheapest first
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.
COS-SJU
COS-MBJ
COS-NAS
COS-GCM
COS-AUA
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
COS-0CB
COS-SJU
COS-MBJ
COS-NAS
COS-GCM
What is the cheapest month to book a flight from Colorado Springs to Caribbean?
Currently, October is the cheapest month in which you can book a flight from Colorado Springs to Caribbean (average of $437). Flying from Colorado Springs to Caribbean in December is currently the most expensive (average of $787). 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 October 15, 2026.
Get a feel of what it's like to fly with Southwest,Delta, andUnited 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.
Crew
8.6
Overall
7.9
Comfort
8.0
Entertainment
7.4
Boarding
8.1
Food
7.0
Reviews
1 / 20
10.0
ExcellentCourtney,Sep 2026
DEN - STL
Crew
8.6
Overall
7.9
Comfort
8.0
Entertainment
7.4
Boarding
8.1
Food
7.0
Reviews
1 / 20
10.0
ExcellentCourtney,Sep 2026
DEN - STL
Crew
8.6
Overall
7.9
Comfort
8.0
Entertainment
7.4
Boarding
8.1
Food
7.0
Reviews
1 / 20
10.0
ExcellentCourtney,Sep 2026
DEN - STL
Crew
8.6
Overall
7.9
Comfort
8.0
Entertainment
7.4
Boarding
8.1
Food
7.0
Reviews
1 / 20
10.0
ExcellentCourtney,Sep 2026
DEN - STL
Crew
8.6
Overall
7.9
Comfort
8.0
Entertainment
7.4
Boarding
8.1
Food
7.0
Reviews
1 / 20
10.0
ExcellentCourtney,Sep 2026
DEN - STL
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.
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Alternative routes for Colorado Springs to Caribbean
See prices for flight routes from nearby airports that may be better suited for you.
Complete your trip
Complete your trip to Caribbean by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Colorado Springs to Caribbean by cabin class
Find flights from Colorado Springs to Caribbean, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Colorado Springs and Caribbean flights
Browse other Colorado Springs and Caribbean flight options. Last updated on October 15, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Fly to Caribbean countries
Consider these flights traveling to countries located in Caribbean.
Colorado Springs to Caribbean flights
Consider these flights traveling from Colorado Springs to Caribbean.
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 7,457,451 searches. Data last updated October 15, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$188 | Average$434 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$265 | Average$573 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$266 | Average$672 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$420 | Average$646 | FlexibilityNo cancel fee | On-time63% |