$231+ 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 8/10. Fares are subject to change and may not be available on all flights or dates of travel.
COS — SJU
Jun 14 — Jun 211
Round-trip
1 adult, Economy
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Find cheap flights from Colorado Springs to Caribbean with Cheapflights
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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
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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 May 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 May 15, 2026.
This United Airlines deal was found by Cheapflights users on 5/10. 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.
Sat 8/225:30 am
COS
- SJU
1 stop10h 08m
United Airlines
Wed 8/262:20 pm
SJU
- COS
2 stops11h 35m
United Airlines
Deal found 5/10![United Airlines logo]()
$283
This American Airlines deal was found by Cheapflights users on 5/10. 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.
Sat 8/225:13 pm
COS
- SJU
2 stops19h 25m
American Airlines
Wed 8/267:14 pm
SJU
- COS
2 stops16h 04m
American Airlines
Deal found 5/10![American Airlines logo]()
$342
This American Airlines deal was found by Cheapflights users on 5/14. 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.
Sat 8/153:51 pm
COS
- SJU
2 stops18h 57m
American Airlines
Wed 8/193:44 pm
SJU
- COS
1 stop9h 09m
American Airlines
Deal found 5/14![American Airlines logo]()
$352
This United Airlines deal was found by Cheapflights users on 5/13. 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 10/207:00 am
COS
- SJU
1 stop8h 38m
United Airlines
Thu 10/291:25 pm
SJU
- COS
1 stop10h 33m
United Airlines
Deal found 5/13![United Airlines logo]()
$356
This United Airlines deal was found by Cheapflights users on 5/13. 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.
Fri 10/237:00 am
COS
- SJU
1 stop8h 38m
United Airlines
Fri 10/301:05 am
SJU
- COS
2 stops12h 13m
United Airlines
Deal found 5/13![United Airlines logo]()
$373
This Delta deal was found by Cheapflights users on 5/13. 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.
Sun 10/256:00 am
COS
- SJU
1 stop8h 33m
Delta
Tue 11/37:30 am
SJU
- COS
1 stop8h 28m
Delta
Deal found 5/13![Delta logo]()
$376
This United Airlines deal was found by Cheapflights users on 5/13. 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 10/206:00 am
COS
- SJU
1 stop9h 38m
United Airlines
Wed 10/281:25 pm
SJU
- COS
1 stop10h 33m
United Airlines
Deal found 5/13![United Airlines logo]()
$391
This American Airlines deal was found by Cheapflights users on 5/13. 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.
Mon 10/268:00 am
COS
- MBJ
1 stop7h 17m
American Airlines
Tue 11/104:02 pm
MBJ
- COS
1 stop9h 46m
American Airlines
Deal found 5/13![American Airlines logo]()
$412
This Delta deal was found by Cheapflights users on 5/13. 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.
Tue 10/206:00 am
COS
- SJU
1 stop8h 33m
Delta
Fri 10/3012:46 pm
SJU
- COS
1 stop10h 35m
Delta
Deal found 5/13![Delta logo]()
$415
This Faresmojo deal was found by Cheapflights users on 5/11. 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 Faresmojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/236:00 am
COS
- SJU
1 stop8h 33m
JetBlue
Sat 6/66:15 am
SJU
- COS
1 stop8h 33m
JetBlue
Deal found 5/11![JetBlue logo]()
$418
This American Airlines deal was found by Cheapflights users on 5/10. 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 11/54:37 pm
COS
- MBJ
2 stops18h 17m
American Airlines
Mon 11/93:14 pm
MBJ
- COS
1 stop22h 52m
American Airlines
Deal found 5/10![American Airlines logo]()
$425
This United Airlines deal was found by Cheapflights users on 5/13. 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 10/216:00 am
COS
- SJU
1 stop9h 38m
United Airlines
Sat 10/316:45 am
SJU
- COS
2 stops15h 23m
United Airlines
Deal found 5/13![United Airlines logo]()
$431
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 May 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 May 15, 2026.
This Southwest deal was found by Cheapflights users on 5/14. 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.
Wed 9/166:15 am
COS
- SJU
2 stops10h 45m
Southwest
Wed 9/238:20 am
SJU
- COS
2 stops10h 40m
Southwest
Deal found 5/14![Southwest logo]()
$356
This Delta deal was found by Cheapflights users on 5/12. 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.
Mon 10/265:55 pm
COS
- SJU
2 stops16h 01m
Delta
Sat 10/317:00 am
SJU
- COS
2 stops17h 30m
Delta
Deal found 5/12![Delta logo]()
$376
This American Airlines deal was found by Cheapflights users on 5/10. 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.
Mon 10/268:00 am
COS
- MBJ
1 stop7h 17m
American Airlines
Tue 11/104:02 pm
MBJ
- COS
1 stop9h 46m
American Airlines
Deal found 5/10![American Airlines logo]()
$412
This United Airlines deal was found by Cheapflights users on 5/12. 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 10/245:30 am
COS
- SJU
2 stops13h 08m
United Airlines
Sat 10/316:45 am
SJU
- COS
2 stops15h 23m
United Airlines
Deal found 5/12![United Airlines logo]()
$431
This American Airlines deal was found by Cheapflights users on 5/10. 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 11/54:37 pm
COS
- MBJ
2 stops18h 17m
American Airlines
Mon 11/93:14 pm
MBJ
- COS
1 stop22h 52m
American Airlines
Deal found 5/10![American Airlines logo]()
$425
This Southwest deal was found by Cheapflights users on 5/10. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/238:55 pm
COS
- SJU
2 stops12h 20m
Southwest
Sat 10/3110:10 am
SJU
- COS
2 stops9h 40m
Southwest
Deal found 5/10![Southwest logo]()
$480
This United Airlines deal was found by Cheapflights users on 5/10. 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.
Fri 10/236:00 am
COS
- SJU
1 stop9h 38m
United Airlines
Sat 10/311:25 pm
SJU
- COS
1 stop8h 43m
United Airlines
Deal found 5/10![United Airlines logo]()
$484
This Delta deal was found by Cheapflights users on 5/10. 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 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 11/102:55 pm
NAS
- COS
1 stop8h 26m
Delta
Deal found 5/10![Delta logo]()
$498
This American Airlines deal was found by Cheapflights users on 5/13. 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.
Sun 11/85:45 am
COS
- MBJ
1 stop7h 14m
American Airlines
Thu 12/33:55 pm
MBJ
- COS
1 stop9h 53m
American Airlines
Deal found 5/13![American Airlines logo]()
$482
This Southwest deal was found by Cheapflights users on 5/13. 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.
Wed 10/147:30 am
COS
- SJU
2 stops12h 45m
Southwest
Mon 10/196:30 am
SJU
- COS
2 stops11h 50m
Southwest
Deal found 5/13![Southwest logo]()
$499
This Delta deal was found by Cheapflights users on 5/12. 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.
Sat 10/245:55 pm
COS
- SJU
2 stops16h 01m
Delta
Mon 11/27:00 am
SJU
- COS
2 stops18h 30m
Delta
Deal found 5/12![Delta logo]()
$501
This American Airlines deal was found by Cheapflights users on 5/10. 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 10/153:51 pm
COS
- PUJ
2 stops20h 34m
American Airlines
Sat 10/245:10 pm
PUJ
- COS
2 stops18h 15m
American Airlines
Deal found 5/10![American Airlines logo]()
$491
This United Airlines deal was found by Cheapflights users on 5/11. 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 8/247:40 am
COS
- SJU
1 stop10h 58m
United Airlines
Wed 8/262:20 pm
SJU
- COS
2 stops11h 35m
United Airlines
Deal found 5/11![United Airlines logo]()
$583
This Delta deal was found by Cheapflights users on 5/13. 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 10/245:55 pm
COS
- SJU
2 stops15h 41m
Delta
Sun 11/11:46 pm
SJU
- COS
1 stop10h 35m
Delta
Deal found 5/13![Delta logo]()
$540
This American Airlines deal was found by Cheapflights users on 5/13. 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.
Sun 8/163:51 pm
COS
- PUJ
2 stops21h 28m
American Airlines
Sat 8/221:38 pm
PUJ
- COS
2 stops21h 40m
American Airlines
Deal found 5/13![American Airlines logo]()
$501
This Southwest deal was found by Cheapflights users on 5/11. 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 6/264:55 pm
COS
- MBJ
2 stops16h 35m
Southwest
Fri 7/33:55 pm
MBJ
- COS
2 stops17h 40m
Southwest
Deal found 5/11![Southwest logo]()
$597
This American Airlines deal was found by Cheapflights users on 5/15. 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 7/163:45 pm
COS
- PUJ
2 stops19h 07m
American Airlines
Mon 7/204:07 pm
PUJ
- COS
2 stops19h 46m
American Airlines
Deal found 5/15![American Airlines logo]()
$501
This United Airlines deal was found by Cheapflights users on 5/12. 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 8/257:40 am
COS
- PUJ
2 stops27h 00m
United Airlines
Thu 8/273:35 pm
PUJ
- COS
2 stops20h 58m
United Airlines
Deal found 5/12![United Airlines logo]()
$611
This American Airlines deal was found by Cheapflights users on 5/14. 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 9/173:51 pm
COS
- PUJ
2 stops20h 44m
American Airlines
Sun 9/203:10 pm
PUJ
- COS
2 stops20h 15m
American Airlines
Deal found 5/14![American Airlines logo]()
$506
This Southwest deal was found by Cheapflights users on 5/13. 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.
Mon 7/1311:10 am
COS
- SJU
2 stops12h 10m
Southwest
Fri 7/176:00 am
SJU
- COS
2 stops12h 00m
Southwest
Deal found 5/13![Southwest logo]()
$613
This American Airlines deal was found by Cheapflights users on 5/14. 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
- PUJ
2 stops18h 54m
American Airlines
Mon 11/95:33 pm
PUJ
- COS
2 stops21h 12m
American Airlines
Deal found 5/14![American Airlines logo]()
$506
This American Airlines deal was found by Cheapflights users on 5/13. 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 11/44:37 pm
COS
- NAS
2 stops16h 30m
American Airlines
Tue 11/1012:07 pm
NAS
- COS
2 stops13h 41m
American Airlines
Deal found 5/13![American Airlines logo]()
$507
This United Airlines deal was found by Cheapflights users on 5/14. 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 9/296:00 am
COS
- SDQ
2 stops14h 46m
United Airlines
Thu 10/16:00 am
SDQ
- COS
2 stops18h 03m
United Airlines
Deal found 5/14![United Airlines logo]()
$750
This American Airlines deal was found by Cheapflights users on 5/14. 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 11/24:37 pm
COS
- SXM
2 stops20h 43m
American Airlines
Tue 11/105:24 pm
SXM
- COS
2 stops19h 30m
American Airlines
Deal found 5/14![American Airlines logo]()
$570
This United Airlines deal was found by Cheapflights users on 5/12. 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 9/285:30 am
COS
- POS
2 stops15h 53m
United Airlines
Tue 9/2912:30 am
POS
- COS
2 stops19h 19m
United Airlines
Deal found 5/12![United Airlines logo]()
$854
This United Airlines deal was found by Cheapflights users on 5/12. 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 5/3011:31 am
COS
- SDQ
2 stops33h 15m
United Airlines
Sat 6/66:00 am
SDQ
- COS
2 stops28h 41m
United Airlines
Deal found 5/12![United Airlines logo]()
$855
This American Airlines deal was found by Cheapflights users on 5/10. 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.
Sat 10/33:51 pm
COS
- PUJ
2 stops20h 44m
American Airlines
Sun 10/115:10 pm
PUJ
- COS
2 stops18h 15m
American Airlines
Deal found 5/10![American Airlines logo]()
$586
This Delta deal was found by Cheapflights users on 5/11. 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.
Tue 9/225:55 pm
COS
- SDQ
2 stops22h 30m
Delta
Sat 9/262:56 pm
SDQ
- COS
1 stop8h 19m
Delta
Deal found 5/11![Delta logo]()
$1,060
This American Airlines deal was found by Cheapflights users on 5/12. 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.
Mon 8/1712:36 pm
COS
- PUJ
1 stop23h 35m
American Airlines
Sat 8/223:40 pm
PUJ
- COS
1 stop19h 38m
American Airlines
Deal found 5/12![American Airlines logo]()
$595
This United Airlines deal was found by Cheapflights users on 5/14. 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 8/37:30 am
COS
- POS
1 stop13h 53m
United Airlines
Fri 8/712:30 am
POS
- COS
2 stops22h 56m
United Airlines
Deal found 5/14![United Airlines logo]()
$934
Last-minute flights from Colorado Springs to CaribbeanDiscover last-minute flight deals from Colorado Springs to Caribbean. Data last updated May 15, 2026 and is based on user searches.
Discover last-minute flight deals from Colorado Springs to Caribbean. Data last updated May 15, 2026 and is based on user searches.
This Southwest deal was found by Cheapflights users on 5/10. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/166:20 am
COS
- SJU
1 stop7h 15m
Southwest
Wed 6/101:30 pm
SJU
- COS
2 stops10h 10m
Southwest
Deal found 5/10![Southwest logo]()
$598
This Southwest deal was found by Cheapflights users on 5/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/196:30 am
COS
- SJU
2 stops12h 35m
Southwest
Tue 6/28:10 am
SJU
- COS
2 stops14h 05m
Southwest
Deal found 5/12![Southwest logo]()
$549
This Southwest deal was found by Cheapflights users on 5/11. 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.
Tue 5/1910:25 am
COS
- SJU
2 stops11h 15m
Southwest
Mon 6/16:50 am
SJU
- COS
2 stops16h 55m
Southwest
Deal found 5/11![Southwest logo]()
$619
This Faresmojo deal was found by Cheapflights users on 5/11. 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 Faresmojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/236:00 am
COS
- SJU
1 stop8h 33m
JetBlue
Sat 6/66:15 am
SJU
- COS
1 stop8h 33m
JetBlue
Deal found 5/11![JetBlue logo]()
$418
This Southwest deal was found by Cheapflights users on 5/11. 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.
Tue 5/2612:40 pm
COS
- SJU
2 stops9h 00m
Southwest
Thu 6/46:30 am
SJU
- COS
1 stop11h 30m
Southwest
Deal found 5/11![Southwest logo]()
$585
This American Airlines deal was found by Cheapflights users on 5/14. 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 5/265:15 pm
COS
- SJU
1 stop9h 10m
American Airlines
Tue 6/26:00 am
SJU
- COS
2 stops12h 34m
American Airlines
Deal found 5/14![American Airlines logo]()
$622
This American Airlines deal was found by Cheapflights users on 5/12. 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 6/63:53 pm
COS
- SXM
2 stops19h 57m
American Airlines
Sat 6/274:43 pm
SXM
- COS
2 stops24h 18m
American Airlines
Deal found 5/12![American Airlines logo]()
$633
This American Airlines deal was found by Cheapflights users on 5/13. 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 6/113:53 pm
COS
- MBJ
2 stops18h 26m
American Airlines
Wed 6/172:08 pm
MBJ
- COS
2 stops20h 45m
American Airlines
Deal found 5/13![American Airlines logo]()
$597
This Southwest deal was found by Cheapflights users on 5/13. 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 6/129:35 am
COS
- SJU
1 stop12h 50m
Southwest
Thu 6/186:00 am
SJU
- COS
2 stops12h 00m
Southwest
Deal found 5/13![Southwest logo]()
$554
This Southwest deal was found by Cheapflights users on 5/12. 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.
Sat 6/1311:25 am
COS
- SJU
2 stops10h 40m
Southwest
Mon 6/156:30 am
SJU
- COS
1 stop11h 30m
Southwest
Deal found 5/12![Southwest logo]()
$616
This American Airlines deal was found by Cheapflights users on 5/10. 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.
Wed 6/243:53 pm
COS
- SDQ
2 stops19h 22m
American Airlines
Wed 7/17:00 am
SDQ
- COS
2 stops17h 24m
American Airlines
Deal found 5/10![American Airlines logo]()
$632
This American Airlines deal was found by Cheapflights users on 5/11. 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 6/253:53 pm
COS
- NAS
2 stops16h 09m
American Airlines
Thu 7/26:05 pm
NAS
- COS
1 stop17h 48m
American Airlines
Deal found 5/11![American Airlines logo]()
$608
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 May 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 May 15, 2026.
This United Airlines deal was found by Cheapflights users on 5/12. 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 8/47:05 am
COS
- PUJ
1 stop8h 30m
United Airlines
Deal found 5/12![United Airlines logo]()
$231
This American Airlines deal was found by Cheapflights users on 5/12. 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 8/45:15 pm
COS
- PUJ
2 stops20h 04m
American Airlines
Deal found 5/12![American Airlines logo]()
$242
This American Airlines deal was found by Cheapflights users on 5/12. 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.
Thu 8/1312:36 pm
COS
- PUJ
1 stop23h 35m
American Airlines
Deal found 5/12![American Airlines logo]()
$251
This Southwest deal was found by Cheapflights users on 5/11. 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.
Tue 5/1910:25 am
COS
- SJU
2 stops11h 15m
Southwest
Deal found 5/11![Southwest logo]()
$261
This Delta deal was found by Cheapflights users on 5/12. 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.
Sun 9/65:55 pm
COS
- SDQ
2 stops22h 09m
Delta
Deal found 5/12![Delta logo]()
$284
This Delta deal was found by Cheapflights users on 5/12. 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.
Sun 8/166:16 pm
COS
- PUJ
2 stops15h 27m
Delta
Deal found 5/12![Delta logo]()
$287
This American Airlines deal was found by Cheapflights users on 5/11. 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 6/28:00 am
COS
- SJU
2 stops11h 59m
American Airlines
Deal found 5/11![American Airlines logo]()
$288
This Southwest deal was found by Cheapflights users on 5/11. 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.
Sat 6/209:55 am
COS
- SJU
2 stops11h 05m
Southwest
Deal found 5/11![Southwest logo]()
$290
This Delta deal was found by Cheapflights users on 5/12. 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.
Mon 9/710:57 am
COS
- SDQ
2 stops24h 15m
Delta
Deal found 5/12![Delta logo]()
$290
This American Airlines deal was found by Cheapflights users on 5/12. 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 8/15:35 am
COS
- PUJ
1 stop8h 29m
American Airlines
Deal found 5/12![American Airlines logo]()
$290
This Delta deal was found by Cheapflights users on 5/12. 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.
Mon 8/311:27 am
COS
- PUJ
2 stops22h 16m
Delta
Deal found 5/12![Delta logo]()
$293
This American Airlines deal was found by Cheapflights users on 5/12. 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.
Wed 8/53:51 pm
COS
- PUJ
2 stops18h 47m
American Airlines
Deal found 5/12![American Airlines logo]()
$295
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 May 15, 2026.
Round-trip from | $283 (United Airlines) |
|---|---|
One-way from | $231 (Delta) |
Popular in | March |
Cheapest in | April |
Average price | $526 |
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 May 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 - SJU
COSSJU
Colorado Springs
Wed 9/16
6:15 am-7:00 pm
2 stops10h 45m
San Juan Luis Munoz Marin Intl
Wed 9/23
8:20 am-5:00 pm
2 stops10h 40m
$356
Colorado SpringsSan Juan
COS - SJU
COSSJU
Colorado Springs
Mon 10/26
5:55 pm-11:56 am
2 stops16h 01m
San Juan Luis Munoz Marin Intl
Sat 10/31
7:00 am-10:30 pm
2 stops17h 30m
$376
Colorado SpringsMontego Bay
COS - MBJ
COSMBJ
Colorado Springs
Mon 10/26
8:00 am-4:17 pm
1 stop7h 17m
Montego Bay Sangster Intl
Tue 11/10
4:02 pm-11:48 pm
1 stop9h 46m
$412
Colorado SpringsMontego Bay
COS - MBJ
COSMBJ
Colorado Springs
Thu 11/5
4:37 pm-12:54 pm
2 stops18h 17m
Montego Bay Sangster Intl
Mon 11/9
3:14 pm-12:06 pm
1 stop22h 52m
$425
Colorado SpringsSan Juan
COS - SJU
COSSJU
Colorado Springs
Sat 10/24
5:30 am-8:38 pm
2 stops13h 08m
San Juan Luis Munoz Marin Intl
Sat 10/31
6:45 am-8:08 pm
2 stops15h 23m
$431
Colorado SpringsSan Juan
COS - SJU
COSSJU
Colorado Springs
Fri 10/23
8:55 pm-11:15 am
2 stops12h 20m
San Juan Luis Munoz Marin Intl
Sat 10/31
10:10 am-5:50 pm
2 stops9h 40m
$480
Colorado SpringsMontego Bay
COS - MBJ
COSMBJ
Colorado Springs
Sun 11/8
5:45 am-2:59 pm
1 stop7h 14m
Montego Bay Sangster Intl
Thu 12/3
3:55 pm-11:48 pm
1 stop9h 53m
$482
Colorado SpringsSan Juan
COS - SJU
COSSJU
Colorado Springs
Fri 10/23
6:00 am-5:38 pm
1 stop9h 38m
San Juan Luis Munoz Marin Intl
Sat 10/31
1:25 pm-8:08 pm
1 stop8h 43m
$484
Colorado SpringsPunta Cana
COS - PUJ
COSPUJ
Colorado Springs
Thu 10/15
3:51 pm-2:25 pm
2 stops20h 34m
Punta Cana
Sat 10/24
5:10 pm-9:25 am
2 stops18h 15m
$491
Quickest round-trip
Colorado SpringsNassau
COS - NAS
COSNAS
Colorado Springs
Wed 11/4
6:00 am-1:49 pm
1 stop5h 49m
Nassau Intl
Tue 11/10
2:55 pm-9:21 pm
1 stop8h 26m
$498
Showing 1-10 of 48 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-PUJ
COS-SJU
COS-SDQ
COS-MBJ
COS-NAS
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-PUJ
COS-SJU
COS-SDQ
COS-MBJ
What is the cheapest month to book a flight from Colorado Springs to Caribbean?
Currently, August is the cheapest month in which you can book a flight from Colorado Springs to Caribbean (average of $193). Flying from Colorado Springs to Caribbean in July is currently the most expensive (average of $539). 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 May 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.
Boarding
8.1
Overall
8.0
Crew
8.6
Food
7.0
Comfort
8.0
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Boarding
8.1
Overall
8.0
Crew
8.6
Food
7.0
Comfort
8.0
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Boarding
8.1
Overall
8.0
Crew
8.6
Food
7.0
Comfort
8.0
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Boarding
8.1
Overall
8.0
Crew
8.6
Food
7.0
Comfort
8.0
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Boarding
8.1
Overall
8.0
Crew
8.6
Food
7.0
Comfort
8.0
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
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 May 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 2,558,603 searches. Data last updated May 15, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$192 | Average$434 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$266 | Average$542 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$272 | Average$721 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$380 | Average$639 | FlexibilityNo cancel fee | On-time63% |