$186+ 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 8/25. Fares are subject to change and may not be available on all flights or dates of travel.
COS ā SJU
Aug 17 ā Aug 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 July 18, 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 July 18, 2026.
This United Airlines deal was found by Cheapflights users on 7/12. Clicking the āPick Datesā button in this card will allow you to select your dates and further customize your flight criteria. From there, click āFind dealsā, make sure United Airlines is selected, and click āCompare selectedā under the list of providers to see comparable flight deals.
Sun 9/67:40 am
COS
- SJU
1 stop10h 58m
United Airlines
Mon 9/141:00 am
SJU
- COS
2 stops11h 47m
United Airlines
Deal found 7/12![United Airlines logo]()
$352
This Southwest deal was found by Cheapflights users on 7/15. Clicking the āPick Datesā button in this card will allow you to select your dates and further customize your flight criteria. From there, click āFind dealsā, make sure Southwest is selected, and click āCompare selectedā under the list of providers to see comparable flight deals.
Tue 8/2510:45 am
COS
- SJU
2 stops9h 15m
Southwest
Fri 8/285:30 am
SJU
- COS
2 stops12h 10m
Southwest
Deal found 7/15![Southwest logo]()
$372
This Delta deal was found by Cheapflights users on 7/15. Clicking the āPick Datesā button in this card will allow you to select your dates and further customize your flight criteria. From there, click āFind dealsā, make sure Delta is selected, and click āCompare selectedā under the list of providers to see comparable flight deals.
Tue 8/256:00 am
COS
- SJU
1 stop8h 38m
Delta
Fri 8/282:59 pm
SJU
- COS
1 stop8h 39m
Delta
Deal found 7/15![Delta logo]()
$376
This Southwest deal was found by Cheapflights users on 7/15. Clicking the āPick Datesā button in this card will allow you to select your dates and further customize your flight criteria. From there, click āFind dealsā, make sure Southwest is selected, and click āCompare selectedā under the list of providers to see comparable flight deals.
Tue 8/256:15 am
COS
- SJU
2 stops10h 45m
Southwest
Sat 8/298:20 am
SJU
- COS
2 stops11h 35m
Southwest
Deal found 7/15![Southwest logo]()
$406
This Southwest deal was found by Cheapflights users on 7/14. Clicking the āPick Datesā button in this card will allow you to select your dates and further customize your flight criteria. From there, click āFind dealsā, make sure Southwest is selected, and click āCompare selectedā under the list of providers to see comparable flight deals.
Sun 8/2311:00 am
COS
- SJU
2 stops11h 30m
Southwest
Sat 8/295:05 am
SJU
- COS
2 stops12h 25m
Southwest
Deal found 7/14![Southwest logo]()
$408
This United Airlines deal was found by Cheapflights users on 7/15. Clicking the āPick Datesā button in this card will allow you to select your dates and further customize your flight criteria. From there, click āFind dealsā, make sure United Airlines is selected, and click āCompare selectedā under the list of providers to see comparable flight deals.
Tue 10/137:40 am
COS
- SJU
1 stop10h 58m
United Airlines
Thu 10/222:00 pm
SJU
- COS
1 stop10h 06m
United Airlines
Deal found 7/15![United Airlines logo]()
$429
This American Airlines deal was found by Cheapflights users on 7/13. Clicking the āPick Datesā button in this card will allow you to select your dates and further customize your flight criteria. From there, click āFind dealsā, make sure American Airlines is selected, and click āCompare selectedā under the list of providers to see comparable flight deals.
Thu 11/512:45 pm
COS
- MBJ
2 stops22h 10m
American Airlines
Wed 11/114:02 pm
MBJ
- COS
1 stop9h 46m
American Airlines
Deal found 7/13![American Airlines logo]()
$437
This United Airlines deal was found by Cheapflights users on 7/13. Clicking the āPick Datesā button in this card will allow you to select your dates and further customize your flight criteria. From there, click āFind dealsā, make sure United Airlines is selected, and click āCompare selectedā under the list of providers to see comparable flight deals.
Tue 9/297:40 am
COS
- SJU
1 stop10h 58m
United Airlines
Fri 10/162:00 pm
SJU
- COS
1 stop10h 06m
United Airlines
Deal found 7/13![United Airlines logo]()
$442
This American Airlines deal was found by Cheapflights users on 7/13. Clicking the āPick Datesā button in this card will allow you to select your dates and further customize your flight criteria. From there, click āFind dealsā, make sure American Airlines is selected, and click āCompare selectedā under the list of providers to see comparable flight deals.
Thu 11/1212:45 pm
COS
- MBJ
1 stop24h 14m
American Airlines
Mon 11/163:50 pm
MBJ
- COS
2 stops20h 04m
American Airlines
Deal found 7/13![American Airlines logo]()
$444
This American Airlines deal was found by Cheapflights users on 7/13. Clicking the āPick Datesā button in this card will allow you to select your dates and further customize your flight criteria. From there, click āFind dealsā, make sure American Airlines is selected, and click āCompare selectedā under the list of providers to see comparable flight deals.
Wed 10/73:58 pm
COS
- MBJ
1 stop23h 14m
American Airlines
Wed 10/1412:16 pm
MBJ
- COS
1 stop11h 43m
American Airlines
Deal found 7/13![American Airlines logo]()
$445
This United Airlines deal was found by Cheapflights users on 7/14. Clicking the āPick Datesā button in this card will allow you to select your dates and further customize your flight criteria. From there, click āFind dealsā, make sure United Airlines is selected, and click āCompare selectedā under the list of providers to see comparable flight deals.
Sun 8/237:40 am
COS
- SJU
1 stop10h 58m
United Airlines
Sat 8/292:00 pm
SJU
- COS
1 stop8h 44m
United Airlines
Deal found 7/14![United Airlines logo]()
$446
This American Airlines deal was found by Cheapflights users on 7/13. Clicking the āPick Datesā button in this card will allow you to select your dates and further customize your flight criteria. From there, click āFind dealsā, make sure American Airlines is selected, and click āCompare selectedā under the list of providers to see comparable flight deals.
Tue 9/2910:14 am
COS
- SJU
2 stops22h 46m
American Airlines
Fri 10/166:20 am
SJU
- COS
2 stops18h 39m
American Airlines
Deal found 7/13![American Airlines logo]()
$458
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 July 18, 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 July 18, 2026.
This United Airlines deal was found by Cheapflights users on 7/12. Clicking the āPick Datesā button in this card will allow you to select your dates and further customize your flight criteria. From there, click āFind dealsā, make sure United Airlines is selected, and click āCompare selectedā under the list of providers to see comparable flight deals.
Sun 9/65:30 am
COS
- SJU
2 stops13h 08m
United Airlines
Mon 9/141:00 am
SJU
- COS
2 stops11h 47m
United Airlines
Deal found 7/12![United Airlines logo]()
$352
This Southwest deal was found by Cheapflights users on 7/15. Clicking the āPick Datesā button in this card will allow you to select your dates and further customize your flight criteria. From there, click āFind dealsā, make sure Southwest is selected, and click āCompare selectedā under the list of providers to see comparable flight deals.
Tue 8/2510:45 am
COS
- SJU
2 stops9h 15m
Southwest
Fri 8/285:30 am
SJU
- COS
2 stops12h 10m
Southwest
Deal found 7/15![Southwest logo]()
$372
This American Airlines deal was found by Cheapflights users on 7/13. Clicking the āPick Datesā button in this card will allow you to select your dates and further customize your flight criteria. From there, click āFind dealsā, make sure American Airlines is selected, and click āCompare selectedā under the list of providers to see comparable flight deals.
Thu 11/54:37 pm
COS
- MBJ
2 stops18h 18m
American Airlines
Wed 11/111:55 pm
MBJ
- COS
2 stops11h 53m
American Airlines
Deal found 7/13![American Airlines logo]()
$437
This Delta deal was found by Cheapflights users on 7/14. Clicking the āPick Datesā button in this card will allow you to select your dates and further customize your flight criteria. From there, click āFind dealsā, make sure Delta is selected, and click āCompare selectedā under the list of providers to see comparable flight deals.
Sun 8/236:16 pm
COS
- SJU
2 stops15h 30m
Delta
Sat 8/2912:56 pm
SJU
- COS
1 stop10h 42m
Delta
Deal found 7/14![Delta logo]()
$480
This United Airlines deal was found by Cheapflights users on 7/15. Clicking the āPick Datesā button in this card will allow you to select your dates and further customize your flight criteria. From there, click āFind dealsā, make sure United Airlines is selected, and click āCompare selectedā under the list of providers to see comparable flight deals.
Tue 8/257:40 am
COS
- SJU
1 stop10h 58m
United Airlines
Sat 8/292:00 pm
SJU
- COS
1 stop7h 54m
United Airlines
Deal found 7/15![United Airlines logo]()
$372
This American Airlines deal was found by Cheapflights users on 7/15. Clicking the āPick Datesā button in this card will allow you to select your dates and further customize your flight criteria. From there, click āFind dealsā, make sure American Airlines is selected, and click āCompare selectedā under the list of providers to see comparable flight deals.
Wed 10/77:57 am
COS
- MBJ
1 stop7h 15m
American Airlines
Wed 10/1412:16 pm
MBJ
- COS
1 stop11h 43m
American Airlines
Deal found 7/15![American Airlines logo]()
$457
This Southwest deal was found by Cheapflights users on 7/15. Clicking the āPick Datesā button in this card will allow you to select your dates and further customize your flight criteria. From there, click āFind dealsā, make sure Southwest is selected, and click āCompare selectedā under the list of providers to see comparable flight deals.
Sat 8/155:45 pm
COS
- SJU
2 stops13h 25m
Southwest
Sat 8/225:05 am
SJU
- COS
2 stops12h 25m
Southwest
Deal found 7/15![Southwest logo]()
$482
This United Airlines deal was found by Cheapflights users on 7/13. Clicking the āPick Datesā button in this card will allow you to select your dates and further customize your flight criteria. From there, click āFind dealsā, make sure United Airlines is selected, and click āCompare selectedā under the list of providers to see comparable flight deals.
Tue 9/297:40 am
COS
- SJU
1 stop10h 58m
United Airlines
Fri 10/162:00 pm
SJU
- COS
1 stop10h 06m
United Airlines
Deal found 7/13![United Airlines logo]()
$442
This American Airlines deal was found by Cheapflights users on 7/17. Clicking the āPick Datesā button in this card will allow you to select your dates and further customize your flight criteria. From there, click āFind dealsā, make sure American Airlines is selected, and click āCompare selectedā under the list of providers to see comparable flight deals.
Sat 8/83:51 pm
COS
- MBJ
1 stop23h 17m
American Airlines
Fri 8/2112:47 pm
MBJ
- COS
1 stop11h 06m
American Airlines
Deal found 7/17![American Airlines logo]()
$502
This United Airlines deal was found by Cheapflights users on 7/15. Clicking the āPick Datesā button in this card will allow you to select your dates and further customize your flight criteria. From there, click āFind dealsā, make sure United Airlines is selected, and click āCompare selectedā under the list of providers to see comparable flight deals.
Wed 9/27:40 am
COS
- SJU
1 stop10h 58m
United Airlines
Thu 9/101:00 am
SJU
- COS
2 stops11h 44m
United Airlines
Deal found 7/15![United Airlines logo]()
$462
This Delta deal was found by Cheapflights users on 7/17. Clicking the āPick Datesā button in this card will allow you to select your dates and further customize your flight criteria. From there, click āFind dealsā, make sure Delta is selected, and click āCompare selectedā 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 7/17![Delta logo]()
$575
This Air Canada deal was found by Cheapflights users on 7/16. Clicking the āPick Datesā button in this card will allow you to select your dates and further customize your flight criteria. From there, click āFind dealsā, make sure Air Canada is selected, and click āCompare selectedā under the list of providers to see comparable flight deals.
Sat 11/146:00 am
COS
- CUR
2 stops30h 45m
Air Canada
Wed 11/184:45 pm
CUR
- COS
2 stops34h 14m
Air Canada
Deal found 7/16![Air Canada logo]()
$1,171
This United Airlines deal was found by Cheapflights users on 7/12. Clicking the āPick Datesā button in this card will allow you to select your dates and further customize your flight criteria. From there, click āFind dealsā, make sure United Airlines is selected, and click āCompare selectedā under the list of providers to see comparable flight deals.
Tue 10/67:00 am
COS
- SJU
1 stop8h 38m
United Airlines
Wed 10/72:55 pm
SJU
- COS
1 stop8h 47m
United Airlines
Deal found 7/12![United Airlines logo]()
$466
This American Airlines deal was found by Cheapflights users on 7/14. Clicking the āPick Datesā button in this card will allow you to select your dates and further customize your flight criteria. From there, click āFind dealsā, make sure American Airlines is selected, and click āCompare selectedā under the list of providers to see comparable flight deals.
Thu 9/1010:14 am
COS
- MBJ
1 stop29h 02m
American Airlines
Mon 9/145:16 pm
MBJ
- COS
2 stops17h 06m
American Airlines
Deal found 7/14![American Airlines logo]()
$530
This Delta deal was found by Cheapflights users on 7/13. Clicking the āPick Datesā button in this card will allow you to select your dates and further customize your flight criteria. From there, click āFind dealsā, make sure Delta is selected, and click āCompare selectedā under the list of providers to see comparable flight deals.
Fri 11/66:00 am
COS
- NAS
1 stop5h 49m
Delta
Tue 11/101:20 pm
NAS
- COS
1 stop10h 01m
Delta
Deal found 7/13![Delta logo]()
$595
This American Airlines deal was found by Cheapflights users on 7/13. Clicking the āPick Datesā button in this card will allow you to select your dates and further customize your flight criteria. From there, click āFind dealsā, make sure American Airlines is selected, and click āCompare selectedā under the list of providers to see comparable flight deals.
Fri 11/612:45 pm
COS
- NAS
1 stop24h 25m
American Airlines
Tue 11/1012:07 pm
NAS
- COS
2 stops13h 41m
American Airlines
Deal found 7/13![American Airlines logo]()
$532
This Delta deal was found by Cheapflights users on 7/14. Clicking the āPick Datesā button in this card will allow you to select your dates and further customize your flight criteria. From there, click āFind dealsā, make sure Delta is selected, and click āCompare selectedā under the list of providers to see comparable flight deals.
Tue 10/131:29 pm
COS
- NAS
2 stops20h 01m
Delta
Tue 10/201:16 pm
NAS
- COS
1 stop8h 51m
Delta
Deal found 7/14![Delta logo]()
$599
This United Airlines deal was found by Cheapflights users on 7/14. Clicking the āPick Datesā button in this card will allow you to select your dates and further customize your flight criteria. From there, click āFind dealsā, make sure United Airlines is selected, and click āCompare selectedā under the list of providers to see comparable flight deals.
Fri 10/27:00 am
COS
- SJU
1 stop8h 38m
United Airlines
Wed 10/212:00 pm
SJU
- COS
1 stop10h 06m
United Airlines
Deal found 7/14![United Airlines logo]()
$496
This American Airlines deal was found by Cheapflights users on 7/17. Clicking the āPick Datesā button in this card will allow you to select your dates and further customize your flight criteria. From there, click āFind dealsā, make sure American Airlines is selected, and click āCompare selectedā under the list of providers to see comparable flight deals.
Mon 8/248:00 am
COS
- MBJ
1 stop7h 08m
American Airlines
Mon 8/3112:47 pm
MBJ
- COS
1 stop21h 31m
American Airlines
Deal found 7/17![American Airlines logo]()
$543
This Delta deal was found by Cheapflights users on 7/13. Clicking the āPick Datesā button in this card will allow you to select your dates and further customize your flight criteria. From there, click āFind dealsā, make sure Delta is selected, and click āCompare selectedā under the list of providers to see comparable flight deals.
Thu 8/2711:27 am
COS
- PUJ
2 stops22h 16m
Delta
Thu 9/31:10 pm
PUJ
- COS
1 stop10h 28m
Delta
Deal found 7/13![Delta logo]()
$631
This United Airlines deal was found by Cheapflights users on 7/12. Clicking the āPick Datesā button in this card will allow you to select your dates and further customize your flight criteria. From there, click āFind dealsā, make sure United Airlines is selected, and click āCompare selectedā under the list of providers to see comparable flight deals.
Mon 11/910:27 am
COS
- MBJ
2 stops23h 46m
United Airlines
Thu 11/121:25 pm
MBJ
- COS
2 stops21h 40m
United Airlines
Deal found 7/12![United Airlines logo]()
$557
This American Airlines deal was found by Cheapflights users on 7/17. Clicking the āPick Datesā button in this card will allow you to select your dates and further customize your flight criteria. From there, click āFind dealsā, make sure American Airlines is selected, and click āCompare selectedā under the list of providers to see comparable flight deals.
Mon 9/78:00 am
COS
- MBJ
1 stop7h 08m
American Airlines
Tue 9/152:09 pm
MBJ
- COS
2 stops20h 13m
American Airlines
Deal found 7/17![American Airlines logo]()
$572
This Delta deal was found by Cheapflights users on 7/15. Clicking the āPick Datesā button in this card will allow you to select your dates and further customize your flight criteria. From there, click āFind dealsā, make sure Delta is selected, and click āCompare selectedā under the list of providers to see comparable flight deals.
Mon 9/76:00 am
COS
- MBJ
1 stop8h 34m
Delta
Tue 9/151:14 pm
MBJ
- COS
1 stop7h 42m
Delta
Deal found 7/15![Delta logo]()
$666
This American Airlines deal was found by Cheapflights users on 7/12. Clicking the āPick Datesā button in this card will allow you to select your dates and further customize your flight criteria. From there, click āFind dealsā, make sure American Airlines is selected, and click āCompare selectedā under the list of providers to see comparable flight deals.
Wed 9/94:08 pm
COS
- MBJ
2 stops19h 45m
American Airlines
Mon 9/145:16 pm
MBJ
- COS
2 stops17h 06m
American Airlines
Deal found 7/12![American Airlines logo]()
$572
This United Airlines deal was found by Cheapflights users on 7/16. Clicking the āPick Datesā button in this card will allow you to select your dates and further customize your flight criteria. From there, click āFind dealsā, make sure United Airlines is selected, and click āCompare selectedā under the list of providers to see comparable flight deals.
Thu 12/31:50 pm
COS
- SXM
2 stops21h 00m
United Airlines
Tue 12/82:52 pm
SXM
- COS
2 stops21h 13m
United Airlines
Deal found 7/16![United Airlines logo]()
$588
This United Airlines deal was found by Cheapflights users on 7/17. Clicking the āPick Datesā button in this card will allow you to select your dates and further customize your flight criteria. From there, click āFind dealsā, make sure United Airlines is selected, and click āCompare selectedā under the list of providers to see comparable flight deals.
Wed 11/411:33 am
COS
- NAS
2 stops24h 00m
United Airlines
Tue 11/102:40 pm
NAS
- COS
1 stop8h 42m
United Airlines
Deal found 7/17![United Airlines logo]()
$594
This Delta deal was found by Cheapflights users on 7/14. Clicking the āPick Datesā button in this card will allow you to select your dates and further customize your flight criteria. From there, click āFind dealsā, make sure Delta is selected, and click āCompare selectedā under the list of providers to see comparable flight deals.
Sat 9/266:14 pm
COS
- AUA
2 stops16h 26m
Delta
Sat 10/31:15 pm
AUA
- COS
1 stop8h 41m
Delta
Deal found 7/14![Delta logo]()
$739
This American Airlines deal was found by Cheapflights users on 7/17. Clicking the āPick Datesā button in this card will allow you to select your dates and further customize your flight criteria. From there, click āFind dealsā, make sure American Airlines is selected, and click āCompare selectedā under the list of providers to see comparable flight deals.
Sat 8/153:51 pm
COS
- UVF
2 stops20h 38m
American Airlines
Sat 8/223:19 pm
UVF
- COS
2 stops19h 59m
American Airlines
Deal found 7/17![American Airlines logo]()
$629
This United Airlines deal was found by Cheapflights users on 7/13. Clicking the āPick Datesā button in this card will allow you to select your dates and further customize your flight criteria. From there, click āFind dealsā, make sure United Airlines is selected, and click āCompare selectedā under the list of providers to see comparable flight deals.
Sun 9/276:03 pm
COS
- PUJ
2 stops16h 37m
United Airlines
Fri 10/23:35 pm
PUJ
- COS
2 stops21h 23m
United Airlines
Deal found 7/13![United Airlines logo]()
$597
This American Airlines deal was found by Cheapflights users on 7/14. Clicking the āPick Datesā button in this card will allow you to select your dates and further customize your flight criteria. From there, click āFind dealsā, make sure American Airlines is selected, and click āCompare selectedā under the list of providers to see comparable flight deals.
Wed 7/295:35 am
COS
- NAS
1 stop7h 12m
American Airlines
Thu 8/67:45 am
NAS
- COS
2 stops17h 08m
American Airlines
Deal found 7/14![American Airlines logo]()
$661
Last-minute flights from Colorado Springs to CaribbeanDiscover last-minute flight deals from Colorado Springs to Caribbean. Data last updated July 18, 2026 and is based on user searches.
Discover last-minute flight deals from Colorado Springs to Caribbean. Data last updated July 18, 2026 and is based on user searches.
This American Airlines deal was found by Cheapflights users on 7/17. Clicking the āPick Datesā button in this card will allow you to select your dates and further customize your flight criteria. From there, click āFind dealsā, make sure American Airlines is selected, and click āCompare selectedā under the list of providers to see comparable flight deals.
Sat 8/85:13 pm
COS
- MBJ
2 stops17h 29m
American Airlines
Fri 8/215:08 pm
MBJ
- COS
2 stops17h 10m
American Airlines
Deal found 7/17![American Airlines logo]()
$498
This Southwest deal was found by Cheapflights users on 7/17. Clicking the āPick Datesā button in this card will allow you to select your dates and further customize your flight criteria. From there, click āFind dealsā, make sure Southwest is selected, and click āCompare selectedā under the list of providers to see comparable flight deals.
Fri 8/1410:25 am
COS
- SJU
2 stops11h 25m
Southwest
Fri 8/215:30 am
SJU
- COS
2 stops12h 10m
Southwest
Deal found 7/17![Southwest logo]()
$460
This American Airlines deal was found by Cheapflights users on 7/17. Clicking the āPick Datesā button in this card will allow you to select your dates and further customize your flight criteria. From there, click āFind dealsā, make sure American Airlines is selected, and click āCompare selectedā under the list of providers to see comparable flight deals.
Fri 8/1412:37 pm
COS
- NAS
2 stops18h 48m
American Airlines
Thu 8/2010:20 am
NAS
- COS
2 stops14h 33m
American Airlines
Deal found 7/17![American Airlines logo]()
$474
This Southwest deal was found by Cheapflights users on 7/16. Clicking the āPick Datesā button in this card will allow you to select your dates and further customize your flight criteria. From there, click āFind dealsā, make sure Southwest is selected, and click āCompare selectedā under the list of providers to see comparable flight deals.
Sat 8/155:45 pm
COS
- SJU
2 stops15h 00m
Southwest
Sat 8/2210:25 am
SJU
- COS
2 stops12h 10m
Southwest
Deal found 7/16![Southwest logo]()
$462
This United Airlines deal was found by Cheapflights users on 7/15. Clicking the āPick Datesā button in this card will allow you to select your dates and further customize your flight criteria. From there, click āFind dealsā, make sure United Airlines is selected, and click āCompare selectedā under the list of providers to see comparable flight deals.
Sat 8/157:40 am
COS
- SJU
1 stop10h 58m
United Airlines
Fri 8/211:00 am
SJU
- COS
2 stops11h 33m
United Airlines
Deal found 7/15![United Airlines logo]()
$509
This Southwest deal was found by Cheapflights users on 7/14. Clicking the āPick Datesā button in this card will allow you to select your dates and further customize your flight criteria. From there, click āFind dealsā, make sure Southwest is selected, and click āCompare selectedā under the list of providers to see comparable flight deals.
Sun 8/2311:00 am
COS
- SJU
2 stops11h 30m
Southwest
Sat 8/295:05 am
SJU
- COS
2 stops12h 25m
Southwest
Deal found 7/14![Southwest logo]()
$408
This United Airlines deal was found by Cheapflights users on 7/14. Clicking the āPick Datesā button in this card will allow you to select your dates and further customize your flight criteria. From there, click āFind dealsā, make sure United Airlines is selected, and click āCompare selectedā under the list of providers to see comparable flight deals.
Sun 8/237:40 am
COS
- SJU
1 stop10h 58m
United Airlines
Sat 8/292:00 pm
SJU
- COS
1 stop8h 44m
United Airlines
Deal found 7/14![United Airlines logo]()
$446
This Delta deal was found by Cheapflights users on 7/14. Clicking the āPick Datesā button in this card will allow you to select your dates and further customize your flight criteria. From there, click āFind dealsā, make sure Delta is selected, and click āCompare selectedā under the list of providers to see comparable flight deals.
Sun 8/236:16 pm
COS
- SJU
2 stops15h 30m
Delta
Sat 8/2912:56 pm
SJU
- COS
1 stop10h 42m
Delta
Deal found 7/14![Delta logo]()
$480
This American Airlines deal was found by Cheapflights users on 7/17. Clicking the āPick Datesā button in this card will allow you to select your dates and further customize your flight criteria. From there, click āFind dealsā, make sure American Airlines is selected, and click āCompare selectedā under the list of providers to see comparable flight deals.
Mon 8/248:00 am
COS
- MBJ
1 stop7h 08m
American Airlines
Mon 8/3112:38 pm
MBJ
- COS
2 stops21h 40m
American Airlines
Deal found 7/17![American Airlines logo]()
$500
This United Airlines deal was found by Cheapflights users on 7/15. Clicking the āPick Datesā button in this card will allow you to select your dates and further customize your flight criteria. From there, click āFind dealsā, make sure United Airlines is selected, and click āCompare selectedā under the list of providers to see comparable flight deals.
Tue 8/257:40 am
COS
- SJU
2 stops14h 10m
United Airlines
Sat 8/292:00 pm
SJU
- COS
1 stop9h 56m
United Airlines
Deal found 7/15![United Airlines logo]()
$372
This Delta deal was found by Cheapflights users on 7/15. Clicking the āPick Datesā button in this card will allow you to select your dates and further customize your flight criteria. From there, click āFind dealsā, make sure Delta is selected, and click āCompare selectedā under the list of providers to see comparable flight deals.
Tue 8/256:00 am
COS
- SJU
1 stop8h 38m
Delta
Fri 8/282:59 pm
SJU
- COS
1 stop8h 39m
Delta
Deal found 7/15![Delta logo]()
$376
This Southwest deal was found by Cheapflights users on 7/15. Clicking the āPick Datesā button in this card will allow you to select your dates and further customize your flight criteria. From there, click āFind dealsā, make sure Southwest is selected, and click āCompare selectedā under the list of providers to see comparable flight deals.
Tue 8/256:15 am
COS
- SJU
2 stops10h 45m
Southwest
Sat 8/298:20 am
SJU
- COS
2 stops11h 35m
Southwest
Deal found 7/15![Southwest logo]()
$406
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 July 18, 2026.
Search for one-way flight options from Colorado Springs to Caribbean. Find affordable one-way fares based on user searches. Data last updated July 18, 2026.
This United Airlines deal was found by Cheapflights users on 7/15. Clicking the āPick Datesā button in this card will allow you to select your dates and further customize your flight criteria. From there, click āFind dealsā, make sure United Airlines is selected, and click āCompare selectedā under the list of providers to see comparable flight deals.
Tue 8/257:40 am
COS
- SJU
1 stop10h 58m
United Airlines
Deal found 7/15![United Airlines logo]()
$186
This Delta deal was found by Cheapflights users on 7/13. Clicking the āPick Datesā button in this card will allow you to select your dates and further customize your flight criteria. From there, click āFind dealsā, make sure Delta is selected, and click āCompare selectedā under the list of providers to see comparable flight deals.
Tue 9/226:00 am
COS
- SJU
1 stop8h 49m
Delta
Deal found 7/13![Delta logo]()
$188
This American Airlines deal was found by Cheapflights users on 7/17. Clicking the āPick Datesā button in this card will allow you to select your dates and further customize your flight criteria. From there, click āFind dealsā, make sure American Airlines is selected, and click āCompare selectedā under the list of providers to see comparable flight deals.
Sat 1/93:17 pm
COS
- SJU
2 stops16h 31m
American Airlines
Deal found 7/17![American Airlines logo]()
$190
This Southwest deal was found by Cheapflights users on 7/16. Clicking the āPick Datesā button in this card will allow you to select your dates and further customize your flight criteria. From there, click āFind dealsā, make sure Southwest is selected, and click āCompare selectedā under the list of providers to see comparable flight deals.
Thu 8/2011:20 am
COS
- SJU
2 stops10h 30m
Southwest
Deal found 7/16![Southwest logo]()
$213
This United Airlines deal was found by Cheapflights users on 7/16. Clicking the āPick Datesā button in this card will allow you to select your dates and further customize your flight criteria. From there, click āFind dealsā, make sure United Airlines is selected, and click āCompare selectedā under the list of providers to see comparable flight deals.
Sun 8/307:40 am
COS
- SJU
1 stop10h 58m
United Airlines
Deal found 7/16![United Airlines logo]()
$230
This United Airlines deal was found by Cheapflights users on 7/15. Clicking the āPick Datesā button in this card will allow you to select your dates and further customize your flight criteria. From there, click āFind dealsā, make sure United Airlines is selected, and click āCompare selectedā under the list of providers to see comparable flight deals.
Tue 9/227:45 am
COS
- SJU
2 stops14h 05m
United Airlines
Deal found 7/15![United Airlines logo]()
$231
This Southwest deal was found by Cheapflights users on 7/17. Clicking the āPick Datesā button in this card will allow you to select your dates and further customize your flight criteria. From there, click āFind dealsā, make sure Southwest is selected, and click āCompare selectedā under the list of providers to see comparable flight deals.
Fri 8/710:25 am
COS
- SJU
2 stops11h 25m
Southwest
Deal found 7/17![Southwest logo]()
$253
This American Airlines deal was found by Cheapflights users on 7/13. Clicking the āPick Datesā button in this card will allow you to select your dates and further customize your flight criteria. From there, click āFind dealsā, make sure American Airlines is selected, and click āCompare selectedā under the list of providers to see comparable flight deals.
Tue 9/2212:37 pm
COS
- SJU
2 stops20h 23m
American Airlines
Deal found 7/13![American Airlines logo]()
$254
This United Airlines deal was found by Cheapflights users on 7/14. Clicking the āPick Datesā button in this card will allow you to select your dates and further customize your flight criteria. From there, click āFind dealsā, make sure United Airlines is selected, and click āCompare selectedā under the list of providers to see comparable flight deals.
Fri 9/118:38 am
COS
- SJU
2 stops13h 12m
United Airlines
Deal found 7/14![United Airlines logo]()
$265
This Delta deal was found by Cheapflights users on 7/13. Clicking the āPick Datesā button in this card will allow you to select your dates and further customize your flight criteria. From there, click āFind dealsā, make sure Delta is selected, and click āCompare selectedā under the list of providers to see comparable flight deals.
Fri 9/116:00 am
COS
- SJU
1 stop8h 49m
Delta
Deal found 7/13![Delta logo]()
$276
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 July 18, 2026.
Round-trip from | $352 (United Airlines) |
|---|---|
One-way from | $186 (United Airlines) |
Popular in | March |
Cheapest in | January |
Average price | $626 |
Cheapflights Fare Finder
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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 July 18, 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
Sun 9/6
5:30 am-8:38 pm
2 stops13h 08m
San Juan Luis Munoz Marin Intl
Mon 9/14
1:00 am-10:47 am
2 stops11h 47m
$352
Colorado SpringsSan Juan
COS - SJU
COSSJU
Colorado Springs
Tue 8/25
10:45 am-10:00 pm
2 stops9h 15m
San Juan Luis Munoz Marin Intl
Fri 8/28
5:30 am-3:40 pm
2 stops12h 10m
$372
Colorado SpringsSan Juan
COS - SJU
COSSJU
Colorado Springs
Tue 8/25
7:40 am-8:38 pm
1 stop10h 58m
San Juan Luis Munoz Marin Intl
Sat 8/29
2:00 pm-7:54 pm
1 stop7h 54m
$372
Colorado SpringsMontego Bay
COS - MBJ
COSMBJ
Colorado Springs
Thu 11/5
4:37 pm-12:55 pm
2 stops18h 18m
Montego Bay Sangster Intl
Wed 11/11
1:55 pm-11:48 pm
2 stops11h 53m
$437
Colorado SpringsSan Juan
COS - SJU
COSSJU
Colorado Springs
Tue 9/29
7:40 am-8:38 pm
1 stop10h 58m
San Juan Luis Munoz Marin Intl
Fri 10/16
2:00 pm-10:06 pm
1 stop10h 06m
$442
Colorado SpringsMontego Bay
COS - MBJ
COSMBJ
Colorado Springs
Wed 10/7
7:57 am-4:12 pm
1 stop7h 15m
Montego Bay Sangster Intl
Wed 10/14
12:16 pm-10:59 pm
1 stop11h 43m
$457
Colorado SpringsSan Juan
COS - SJU
COSSJU
Colorado Springs
Wed 9/2
7:40 am-8:38 pm
1 stop10h 58m
San Juan Luis Munoz Marin Intl
Thu 9/10
1:00 am-10:44 am
2 stops11h 44m
$462
Colorado SpringsSan Juan
COS - SJU
COSSJU
Colorado Springs
Tue 10/6
7:00 am-5:38 pm
1 stop8h 38m
San Juan Luis Munoz Marin Intl
Wed 10/7
2:55 pm-9:42 pm
1 stop8h 47m
$466
Colorado SpringsSan Juan
COS - SJU
COSSJU
Colorado Springs
Sun 8/23
6:16 pm-11:46 am
2 stops15h 30m
San Juan Luis Munoz Marin Intl
Sat 8/29
12:56 pm-9:38 pm
1 stop10h 42m
$480
Colorado SpringsSan Juan
COS - SJU
COSSJU
Colorado Springs
Sat 8/15
5:45 pm-9:10 am
2 stops13h 25m
San Juan Luis Munoz Marin Intl
Sat 8/22
5:05 am-3:30 pm
2 stops12h 25m
$482
Showing 1-10 of 40 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-NAS
COS-MBJ
COS-CUR
COS-PUJ
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-NAS
COS-MBJ
COS-CUR
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 $420). Flying from Colorado Springs to Caribbean in March is currently the most expensive (average of $736). 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 July 18, 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.
Food
7.0
Boarding
8.1
Crew
8.6
Comfort
8.0
Overall
8.0
Entertainment
7.5
Reviews
1 / 20
8.0
ExcellentAnonymous,Feb 2026
DEN - BDL
Food
7.0
Boarding
8.1
Crew
8.6
Comfort
8.0
Overall
8.0
Entertainment
7.5
Reviews
1 / 20
8.0
ExcellentAnonymous,Feb 2026
DEN - BDL
Food
7.0
Boarding
8.1
Crew
8.6
Comfort
8.0
Overall
8.0
Entertainment
7.5
Reviews
1 / 20
8.0
ExcellentAnonymous,Feb 2026
DEN - BDL
Food
7.0
Boarding
8.1
Crew
8.6
Comfort
8.0
Overall
8.0
Entertainment
7.5
Reviews
1 / 20
8.0
ExcellentAnonymous,Feb 2026
DEN - BDL
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 July 18, 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 July 18, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$266 | Average$694 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$272 | Average$721 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$380 | Average$646 | FlexibilityNo cancel fee | On-time63% |