$176+ 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 9/22. Fares are subject to change and may not be available on all flights or dates of travel.
COS — SJU
Jul 17 — Jul 241
Round-trip
1 adult, Economy
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Find cheap flights from Colorado Springs to Caribbean with Cheapflights
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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 June 17, 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 June 17, 2026.
This American Airlines deal was found by Cheapflights users on 6/14. 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.
Thu 8/275:13 pm
COS
- SJU
2 stops17h 27m
American Airlines
Wed 9/23:44 pm
SJU
- COS
1 stop9h 09m
American Airlines
Deal found 6/14![American Airlines logo]()
$352
This Southwest deal was found by Cheapflights users on 6/16. 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.
Wed 10/1410:30 am
COS
- SJU
2 stops11h 15m
Southwest
Fri 10/235:30 am
SJU
- COS
2 stops12h 50m
Southwest
Deal found 6/16![Southwest logo]()
$374
This Delta deal was found by Cheapflights users on 6/15. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/256:14 pm
COS
- SJU
2 stops15h 59m
Delta
Sun 9/2712:58 pm
SJU
- COS
1 stop8h 38m
Delta
Deal found 6/15![Delta logo]()
$376
This United Airlines deal was found by Cheapflights users on 6/15. 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 9/257:40 am
COS
- SJU
1 stop10h 58m
United Airlines
Sun 9/272:00 pm
SJU
- COS
1 stop10h 06m
United Airlines
Deal found 6/15![United Airlines logo]()
$410
This Southwest deal was found by Cheapflights users on 6/16. 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.
Mon 10/58:55 pm
COS
- SJU
2 stops11h 45m
Southwest
Mon 10/126:30 am
SJU
- COS
2 stops11h 50m
Southwest
Deal found 6/16![Southwest logo]()
$413
This Southwest deal was found by Cheapflights users on 6/15. 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 9/2510:25 am
COS
- SJU
2 stops11h 25m
Southwest
Sun 9/276:00 am
SJU
- COS
2 stops12h 10m
Southwest
Deal found 6/15![Southwest logo]()
$420
This United Airlines deal was found by Cheapflights users on 6/16. 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.
Mon 10/56:00 am
COS
- SJU
1 stop9h 38m
United Airlines
Mon 10/122:00 pm
SJU
- COS
1 stop10h 06m
United Airlines
Deal found 6/16![United Airlines logo]()
$421
This United Airlines deal was found by Cheapflights users on 6/13. 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 8/16:00 am
COS
- MBJ
1 stop8h 45m
United Airlines
Fri 8/74:12 pm
MBJ
- COS
2 stops17h 29m
United Airlines
Deal found 6/13![United Airlines logo]()
$427
This American Airlines deal was found by Cheapflights users on 6/13. 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.
Thu 11/512:45 pm
COS
- MBJ
1 stop24h 14m
American Airlines
Mon 11/93:50 pm
MBJ
- COS
2 stops20h 04m
American Airlines
Deal found 6/13![American Airlines logo]()
$434
This Southwest deal was found by Cheapflights users on 6/14. 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.
Thu 10/2911:15 am
COS
- SJU
2 stops11h 20m
Southwest
Sat 11/77:45 am
SJU
- COS
2 stops12h 30m
Southwest
Deal found 6/14![Southwest logo]()
$435
This American Airlines deal was found by Cheapflights users on 6/15. 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 10/1612:26 pm
COS
- MBJ
1 stop22h 40m
American Airlines
Sat 10/241:10 pm
MBJ
- COS
2 stops21h 15m
American Airlines
Deal found 6/15![American Airlines logo]()
$435
This United Airlines deal was found by Cheapflights users on 6/13. 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 9/125:30 am
COS
- SJU
2 stops13h 08m
United Airlines
Wed 9/163:00 pm
SJU
- COS
2 stops10h 55m
United Airlines
Deal found 6/13![United Airlines logo]()
$442
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 June 17, 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 June 17, 2026.
This American Airlines deal was found by Cheapflights users on 6/13. 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.
Fri 9/114:57 pm
COS
- SJU
2 stops20h 43m
American Airlines
Fri 9/182:58 pm
SJU
- COS
2 stops20h 24m
American Airlines
Deal found 6/13![American Airlines logo]()
$352
This Delta deal was found by Cheapflights users on 6/15. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/256:14 pm
COS
- SJU
2 stops15h 59m
Delta
Sun 9/2712:58 pm
SJU
- COS
1 stop8h 38m
Delta
Deal found 6/15![Delta logo]()
$376
This Southwest deal was found by Cheapflights users on 6/13. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/2510:25 am
COS
- SJU
2 stops11h 25m
Southwest
Sun 9/276:00 am
SJU
- COS
2 stops12h 10m
Southwest
Deal found 6/13![Southwest logo]()
$415
This United 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/125:30 am
COS
- SJU
2 stops13h 08m
United Airlines
Wed 9/163:00 pm
SJU
- COS
2 stops10h 55m
United Airlines
Deal found 6/12![United Airlines logo]()
$442
This Delta deal was found by Cheapflights users on 6/13. 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.
Sat 9/126:00 am
COS
- SJU
1 stop8h 49m
Delta
Fri 9/1812:58 pm
SJU
- COS
1 stop8h 38m
Delta
Deal found 6/13![Delta logo]()
$415
This American Airlines deal was found by Cheapflights users on 6/15. 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 10/163:51 pm
COS
- MBJ
2 stops19h 49m
American Airlines
Sat 10/241:10 pm
MBJ
- COS
2 stops21h 15m
American Airlines
Deal found 6/15![American Airlines logo]()
$427
This Southwest deal was found by Cheapflights users on 6/14. 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.
Thu 10/2911:15 am
COS
- SJU
2 stops11h 20m
Southwest
Sat 11/77:45 am
SJU
- COS
2 stops12h 30m
Southwest
Deal found 6/14![Southwest logo]()
$435
This American Airlines deal was found by Cheapflights users on 6/13. 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.
Thu 11/54:37 pm
COS
- MBJ
2 stops20h 13m
American Airlines
Mon 11/93:50 pm
MBJ
- COS
2 stops20h 04m
American Airlines
Deal found 6/13![American Airlines logo]()
$427
This United Airlines deal was found by Cheapflights users on 6/13. 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 9/125:30 am
COS
- SJU
2 stops13h 08m
United Airlines
Fri 9/181:00 am
SJU
- COS
2 stops11h 47m
United Airlines
Deal found 6/13![United Airlines logo]()
$473
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.
Thu 7/99:35 am
COS
- SJU
1 stop13h 00m
Southwest
Thu 7/166:30 am
SJU
- COS
1 stop11h 30m
Southwest
Deal found 6/12![Southwest logo]()
$496
This United Airlines deal was found by Cheapflights users on 6/15. 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 10/166:03 pm
COS
- MBJ
1 stop20h 42m
United Airlines
Sat 10/2412:52 pm
MBJ
- COS
1 stop8h 17m
United Airlines
Deal found 6/15![United Airlines logo]()
$506
This Delta deal was found by Cheapflights users on 6/15. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/186:00 am
COS
- NAS
1 stop5h 49m
Delta
Wed 9/233:14 pm
NAS
- COS
1 stop6h 22m
Delta
Deal found 6/15![Delta logo]()
$508
This United Airlines deal was found by Cheapflights users on 6/16. 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.
Tue 7/145:13 pm
COS
- NAS
2 stops16h 15m
United Airlines
Mon 7/204:58 pm
NAS
- COS
1 stop6h 31m
United Airlines
Deal found 6/16![United Airlines logo]()
$508
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 9/183:53 pm
COS
- NAS
2 stops19h 33m
American Airlines
Wed 9/236:45 pm
NAS
- COS
2 stops16h 37m
American Airlines
Deal found 6/12![American Airlines logo]()
$512
This Southwest deal was found by Cheapflights users on 6/16. 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 7/99:35 am
COS
- SJU
1 stop13h 00m
Southwest
Mon 7/136:30 am
SJU
- COS
1 stop11h 30m
Southwest
Deal found 6/16![Southwest logo]()
$545
This American Airlines deal was found by Cheapflights users on 6/15. 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 7/141:07 pm
COS
- NAS
2 stops18h 20m
American Airlines
Mon 7/207:39 am
NAS
- COS
2 stops16h 44m
American Airlines
Deal found 6/15![American Airlines logo]()
$512
This Delta deal was found by Cheapflights users on 6/16. 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.
Wed 11/46:00 am
COS
- NAS
1 stop5h 49m
Delta
Tue 11/104:55 pm
NAS
- COS
1 stop6h 26m
Delta
Deal found 6/16![Delta logo]()
$565
This United Airlines deal was found by Cheapflights users on 6/13. 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 8/11:30 pm
COS
- MBJ
2 stops23h 00m
United Airlines
Fri 8/74:12 pm
MBJ
- COS
2 stops17h 29m
United Airlines
Deal found 6/13![United Airlines logo]()
$547
This American Airlines deal was found by Cheapflights users on 6/14. 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.
Wed 11/44:37 pm
COS
- NAS
2 stops16h 30m
American Airlines
Tue 11/1010:40 am
NAS
- COS
2 stops15h 08m
American Airlines
Deal found 6/14![American Airlines logo]()
$517
This American Airlines deal was found by Cheapflights users on 6/13. 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.
Thu 10/153:51 pm
COS
- PUJ
2 stops20h 39m
American Airlines
Sat 10/241:25 pm
PUJ
- COS
2 stops22h 00m
American Airlines
Deal found 6/13![American Airlines logo]()
$521
This Southwest deal was found by Cheapflights users on 6/14. 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.
Mon 6/294:55 pm
COS
- MBJ
2 stops17h 40m
Southwest
Fri 7/32:20 pm
MBJ
- COS
2 stops19h 15m
Southwest
Deal found 6/14![Southwest logo]()
$664
This United Airlines deal was found by Cheapflights users on 6/15. 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.
Wed 7/153:02 pm
COS
- MBJ
2 stops19h 41m
United Airlines
Tue 7/214:12 pm
MBJ
- COS
2 stops17h 29m
United Airlines
Deal found 6/15![United Airlines logo]()
$612
This American Airlines deal was found by Cheapflights users on 6/15. 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 12/44:34 pm
COS
- PUJ
2 stops19h 57m
American Airlines
Sat 12/125:30 pm
PUJ
- COS
2 stops21h 18m
American Airlines
Deal found 6/15![American Airlines logo]()
$521
This United Airlines deal was found by Cheapflights users on 6/13. 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.
Sun 11/112:50 pm
COS
- MBJ
2 stops21h 17m
United Airlines
Wed 11/41:25 pm
MBJ
- COS
2 stops21h 40m
United Airlines
Deal found 6/13![United Airlines logo]()
$623
This American Airlines deal was found by Cheapflights users on 6/13. 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 11/45:45 am
COS
- PUJ
1 stop8h 07m
American Airlines
Mon 11/95:47 pm
PUJ
- COS
2 stops20h 58m
American Airlines
Deal found 6/13![American Airlines logo]()
$526
This American Airlines deal was found by Cheapflights users on 6/13. 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.
Thu 9/173:53 pm
COS
- PUJ
2 stops21h 19m
American Airlines
Sun 9/2011:44 am
PUJ
- COS
2 stops23h 38m
American Airlines
Deal found 6/13![American Airlines logo]()
$526
This United Airlines deal was found by Cheapflights users on 6/13. 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.
Mon 9/2111:30 am
COS
- PUJ
2 stops26h 00m
United Airlines
Thu 9/241:50 pm
PUJ
- COS
2 stops20h 50m
United Airlines
Deal found 6/13![United Airlines logo]()
$641
This American Airlines deal was found by Cheapflights users on 6/15. 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.
Sat 12/512:45 pm
COS
- PUJ
2 stops19h 56m
American Airlines
Sat 12/123:51 pm
PUJ
- COS
1 stop22h 57m
American Airlines
Deal found 6/15![American Airlines logo]()
$529
This United Airlines deal was found by Cheapflights users on 6/17. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/16:00 am
COS
- MBJ
1 stop8h 45m
United Airlines
Sat 8/812:52 pm
MBJ
- COS
1 stop10h 14m
United Airlines
Deal found 6/17![United Airlines logo]()
$656
This American Airlines deal was found by Cheapflights users on 6/15. 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.
Thu 7/303:46 pm
COS
- SXM
2 stops20h 00m
American Airlines
Thu 8/62:42 pm
SXM
- COS
2 stops24h 05m
American Airlines
Deal found 6/15![American Airlines logo]()
$551
Last-minute flights from Colorado Springs to CaribbeanDiscover last-minute flight deals from Colorado Springs to Caribbean. Data last updated June 17, 2026 and is based on user searches.
Discover last-minute flight deals from Colorado Springs to Caribbean. Data last updated June 17, 2026 and is based on user searches.
This Southwest deal was found by Cheapflights users on 6/15. 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 6/199:35 am
COS
- SJU
1 stop12h 50m
Southwest
Sun 6/215:45 am
SJU
- COS
1 stop13h 00m
Southwest
Deal found 6/15![Southwest logo]()
$580
This Southwest deal was found by Cheapflights users on 6/13. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/1911:10 am
COS
- SJU
2 stops10h 55m
Southwest
Fri 6/266:00 am
SJU
- COS
2 stops12h 00m
Southwest
Deal found 6/13![Southwest logo]()
$620
This Southwest deal was found by Cheapflights users on 6/16. 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.
Wed 6/2412:10 pm
COS
- SJU
2 stops10h 05m
Southwest
Tue 6/306:30 am
SJU
- COS
1 stop14h 45m
Southwest
Deal found 6/16![Southwest logo]()
$561
This Southwest deal was found by Cheapflights users on 6/15. 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.
Sat 7/48:20 am
COS
- SJU
2 stops9h 15m
Southwest
Thu 7/96:30 am
SJU
- COS
1 stop11h 30m
Southwest
Deal found 6/15![Southwest logo]()
$569
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.
Thu 7/99:35 am
COS
- SJU
1 stop13h 00m
Southwest
Thu 7/166:30 am
SJU
- COS
1 stop11h 30m
Southwest
Deal found 6/12![Southwest logo]()
$496
This Southwest deal was found by Cheapflights users on 6/16. 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 7/99:35 am
COS
- SJU
1 stop13h 00m
Southwest
Mon 7/136:30 am
SJU
- COS
1 stop11h 30m
Southwest
Deal found 6/16![Southwest logo]()
$545
This United Airlines deal was found by Cheapflights users on 6/16. 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.
Tue 7/147:30 am
COS
- NAS
1 stop6h 26m
United Airlines
Mon 7/204:58 pm
NAS
- COS
1 stop6h 31m
United Airlines
Deal found 6/16![United Airlines logo]()
$508
This United Airlines deal was found by Cheapflights users on 6/15. 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.
Wed 7/153:02 pm
COS
- MBJ
2 stops19h 41m
United Airlines
Tue 7/214:12 pm
MBJ
- COS
2 stops17h 29m
United Airlines
Deal found 6/15![United Airlines logo]()
$612
This American Airlines deal was found by Cheapflights users on 6/16. 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.
Thu 7/163:46 pm
COS
- MBJ
2 stops20h 45m
American Airlines
Thu 7/232:09 pm
MBJ
- COS
2 stops20h 43m
American Airlines
Deal found 6/16![American Airlines logo]()
$571
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.
Sat 7/253:49 pm
COS
- PUJ
2 stops19h 03m
American Airlines
Fri 7/314:50 pm
PUJ
- COS
2 stops19h 02m
American Airlines
Deal found 6/12![American Airlines logo]()
$597
This Southwest deal was found by Cheapflights users on 6/16. 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.
Mon 7/279:35 am
COS
- SJU
1 stop13h 00m
Southwest
Fri 7/316:30 am
SJU
- COS
1 stop11h 30m
Southwest
Deal found 6/16![Southwest logo]()
$587
This American Airlines deal was found by Cheapflights users on 6/15. 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.
Thu 7/303:46 pm
COS
- SXM
2 stops20h 00m
American Airlines
Thu 8/62:42 pm
SXM
- COS
2 stops24h 05m
American Airlines
Deal found 6/15![American Airlines logo]()
$551
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 June 17, 2026.
Search for one-way flight options from Colorado Springs to Caribbean. Find affordable one-way fares based on user searches. Data last updated June 17, 2026.
This American Airlines deal was found by Cheapflights users on 6/16. 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.
Tue 9/224:08 pm
COS
- SJU
2 stops19h 46m
American Airlines
Deal found 6/16![American Airlines logo]()
$176
This American Airlines deal was found by Cheapflights users on 6/16. 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 9/114:57 pm
COS
- SJU
2 stops18h 57m
American Airlines
Deal found 6/16![American Airlines logo]()
$182
This Delta deal was found by Cheapflights users on 6/16. 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.
Tue 9/226:00 am
COS
- SJU
1 stop8h 31m
Delta
Deal found 6/16![Delta logo]()
$188
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 7/218:01 am
COS
- SJU
2 stops11h 58m
American Airlines
Deal found 6/12![American Airlines logo]()
$212
This United Airlines deal was found by Cheapflights users on 6/13. 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 9/125:30 am
COS
- SJU
2 stops13h 08m
United Airlines
Deal found 6/13![United Airlines logo]()
$221
This Delta deal was found by Cheapflights users on 6/16. 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.
Fri 9/116:00 am
COS
- SJU
1 stop8h 49m
Delta
Deal found 6/16![Delta logo]()
$227
This United 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/246:32 pm
COS
- PUJ
1 stop21h 03m
United Airlines
Deal found 6/12![United Airlines logo]()
$258
This Southwest deal was found by Cheapflights users on 6/15. 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.
Wed 6/2412:10 pm
COS
- SJU
2 stops10h 05m
Southwest
Deal found 6/15![Southwest logo]()
$266
This United Airlines deal was found by Cheapflights users on 6/17. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/267:30 am
COS
- MBJ
1 stop29h 00m
United Airlines
Deal found 6/17![United Airlines logo]()
$268
This United Airlines deal was found by Cheapflights users on 6/15. 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.
Tue 6/301:30 pm
COS
- SJU
2 stops13h 59m
United Airlines
Deal found 6/15![United Airlines logo]()
$306
This United 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/223:42 pm
COS
- SJU
2 stops11h 47m
United Airlines
Deal found 6/12![United Airlines logo]()
$308
This Southwest deal was found by Cheapflights users on 6/15. 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.
Tue 6/3012:10 pm
COS
- SJU
2 stops10h 05m
Southwest
Deal found 6/15![Southwest logo]()
$325
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 June 17, 2026.
Round-trip from | $352 (American Airlines) |
|---|---|
One-way from | $176 (American Airlines) |
Popular in | March |
Cheapest in | January |
Average price | $614 |
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 June 17, 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 - SJU
COSSJU
Colorado Springs
Fri 9/11
4:57 pm-3:40 pm
2 stops20h 43m
San Juan Luis Munoz Marin Intl
Fri 9/18
2:58 pm-9:22 am
2 stops20h 24m
$352
Colorado SpringsSan Juan
COS - SJU
COSSJU
Colorado Springs
Fri 9/25
6:14 pm-12:13 pm
2 stops15h 59m
San Juan Luis Munoz Marin Intl
Sun 9/27
12:58 pm-7:36 pm
1 stop8h 38m
$376
Colorado SpringsSan Juan
COS - SJU
COSSJU
Colorado Springs
Fri 9/25
10:25 am-11:50 pm
2 stops11h 25m
San Juan Luis Munoz Marin Intl
Sun 9/27
6:00 am-4:10 pm
2 stops12h 10m
$415
Colorado SpringsSan Juan
COS - SJU
COSSJU
Colorado Springs
Sat 9/12
6:00 am-4:49 pm
1 stop8h 49m
San Juan Luis Munoz Marin Intl
Fri 9/18
12:58 pm-7:36 pm
1 stop8h 38m
$415
Colorado SpringsMontego Bay
COS - MBJ
COSMBJ
Colorado Springs
Fri 10/16
3:51 pm-12:40 pm
2 stops19h 49m
Montego Bay Sangster Intl
Sat 10/24
1:10 pm-9:25 am
2 stops21h 15m
$427
Colorado SpringsMontego Bay
COS - MBJ
COSMBJ
Colorado Springs
Thu 11/5
4:37 pm-2:50 pm
2 stops20h 13m
Montego Bay Sangster Intl
Mon 11/9
3:50 pm-9:54 am
2 stops20h 04m
$427
Colorado SpringsSan Juan
COS - SJU
COSSJU
Colorado Springs
Thu 10/29
11:15 am-12:35 am
2 stops11h 20m
San Juan Luis Munoz Marin Intl
Sat 11/7
7:45 am-5:15 pm
2 stops12h 30m
$435
Colorado SpringsSan Juan
COS - SJU
COSSJU
Colorado Springs
Sat 9/12
5:30 am-8:38 pm
2 stops13h 08m
San Juan Luis Munoz Marin Intl
Wed 9/16
3:00 pm-11:55 pm
2 stops10h 55m
$442
Colorado SpringsSan Juan
COS - SJU
COSSJU
Colorado Springs
Sat 9/12
5:30 am-8:38 pm
2 stops13h 08m
San Juan Luis Munoz Marin Intl
Fri 9/18
1:00 am-10:47 am
2 stops11h 47m
$473
Colorado SpringsSan Juan
COS - SJU
COSSJU
Colorado Springs
Thu 7/9
9:35 am-12:35 am
1 stop13h 00m
San Juan Luis Munoz Marin Intl
Thu 7/16
6:30 am-4:00 pm
1 stop11h 30m
$496
Showing 1-10 of 42 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-PUJ
COS-MBJ
COS-NAS
COS-SXM
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-PUJ
COS-MBJ
COS-NAS
What is the cheapest month to book a flight from Colorado Springs to Caribbean?
Currently, January is the cheapest month in which you can book a flight from Colorado Springs to Caribbean (average of $265). Flying from Colorado Springs to Caribbean in March is currently the most expensive (average of $512). 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 June 17, 2026.
Get a feel of what it's like to fly with Southwest,United Airlines, andAmerican 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.
Comfort
8.0
Entertainment
7.5
Overall
7.9
Food
7.0
Crew
8.6
Boarding
8.1
Reviews
1 / 20
8.0
ExcellentLa Tracimeldamarcos,Jun 2026
LAX - SLC
Comfort
8.0
Entertainment
7.5
Overall
7.9
Food
7.0
Crew
8.6
Boarding
8.1
Reviews
1 / 20
8.0
ExcellentLa Tracimeldamarcos,Jun 2026
LAX - SLC
Comfort
8.0
Entertainment
7.5
Overall
7.9
Food
7.0
Crew
8.6
Boarding
8.1
Reviews
1 / 20
8.0
ExcellentLa Tracimeldamarcos,Jun 2026
LAX - SLC
Comfort
8.0
Entertainment
7.5
Overall
7.9
Food
7.0
Crew
8.6
Boarding
8.1
Reviews
1 / 20
8.0
ExcellentLa Tracimeldamarcos,Jun 2026
LAX - SLC
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 June 17, 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 3 airlines flying from Colorado Springs to Caribbean
Discover the top 3 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 June 17, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$266 | Average$588 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$272 | Average$721 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$380 | Average$648 | FlexibilityNo cancel fee | On-time63% |