$150+ 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 8/15. Fares are subject to change and may not be available on all flights or dates of travel.
COS — SJU
May 29 — Jun 51
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 April 29, 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 April 29, 2026.
This United Airlines deal was found by Cheapflights users on 4/28. 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 9/15:30 am
COS
- SJU
2 stops13h 08m
United Airlines
Tue 9/221:00 am
SJU
- COS
2 stops11h 59m
United Airlines
Deal found 4/28![United Airlines logo]()
$322
This American Airlines deal was found by Cheapflights users on 4/28. 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 9/153:51 pm
COS
- SJU
2 stops20h 54m
American Airlines
Tue 10/135:50 pm
SJU
- COS
2 stops17h 35m
American Airlines
Deal found 4/28![American Airlines logo]()
$342
This American Airlines deal was found by Cheapflights users on 4/29. 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
- SJU
2 stops18h 57m
American Airlines
Sun 8/233:44 pm
SJU
- COS
1 stop9h 09m
American Airlines
Deal found 4/29![American Airlines logo]()
$379
This American Airlines deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/175:45 am
COS
- MBJ
1 stop7h 14m
American Airlines
Sun 11/223:50 pm
MBJ
- COS
2 stops20h 04m
American Airlines
Deal found 4/28![American Airlines logo]()
$402
This American Airlines deal was found by Cheapflights users on 4/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/145:13 pm
COS
- MBJ
2 stops19h 12m
American Airlines
Tue 5/2612:31 pm
MBJ
- COS
2 stops22h 23m
American Airlines
Deal found 4/26![American Airlines logo]()
$447
This American Airlines deal was found by Cheapflights users on 4/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/181:39 pm
COS
- SJU
2 stops17h 34m
American Airlines
Wed 6/37:15 pm
SJU
- COS
2 stops16h 38m
American Airlines
Deal found 4/26![American Airlines logo]()
$456
This American Airlines deal was found by Cheapflights users on 4/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/93:45 pm
COS
- MBJ
2 stops19h 02m
American Airlines
Thu 7/165:17 pm
MBJ
- COS
2 stops19h 27m
American Airlines
Deal found 4/25![American Airlines logo]()
$467
This Delta deal was found by Cheapflights users on 4/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/26:15 am
COS
- SJU
1 stop8h 08m
Delta
Sat 5/91:14 pm
SJU
- COS
1 stop10h 13m
Delta
Deal found 4/26![Delta logo]()
$478
This American Airlines deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/612:22 pm
COS
- STT
2 stops21h 13m
American Airlines
Wed 5/135:05 pm
STT
- COS
2 stops18h 22m
American Airlines
Deal found 4/27![American Airlines logo]()
$480
This Delta deal was found by Cheapflights users on 4/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/196:00 am
COS
- SDQ
2 stops16h 38m
Delta
Fri 7/37:35 pm
SDQ
- COS
2 stops16h 55m
Delta
Deal found 4/26![Delta logo]()
$491
This Delta deal was found by Cheapflights users on 4/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/245:55 pm
COS
- PUJ
2 stops18h 36m
Delta
Thu 10/292:49 pm
PUJ
- COS
1 stop8h 32m
Delta
Deal found 4/25![Delta logo]()
$491
This American Airlines deal was found by Cheapflights users on 4/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/243:51 pm
COS
- PUJ
1 stop22h 09m
American Airlines
Fri 10/305:00 pm
PUJ
- COS
1 stop18h 25m
American Airlines
Deal found 4/25![American Airlines logo]()
$494
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 April 29, 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 April 29, 2026.
This United Airlines deal was found by Cheapflights users on 4/28. 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 9/15:30 am
COS
- SJU
2 stops13h 08m
United Airlines
Tue 9/221:00 am
SJU
- COS
2 stops11h 59m
United Airlines
Deal found 4/28![United Airlines logo]()
$322
This American Airlines deal was found by Cheapflights users on 4/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/145:13 pm
COS
- MBJ
2 stops19h 12m
American Airlines
Tue 5/2612:31 pm
MBJ
- COS
2 stops22h 23m
American Airlines
Deal found 4/26![American Airlines logo]()
$447
This Delta deal was found by Cheapflights users on 4/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/196:00 am
COS
- SDQ
2 stops16h 38m
Delta
Fri 7/37:35 pm
SDQ
- COS
2 stops16h 55m
Delta
Deal found 4/26![Delta logo]()
$491
This Southwest deal was found by Cheapflights users on 4/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/118:00 pm
COS
- SJU
2 stops12h 35m
Southwest
Fri 5/156:50 am
SJU
- COS
2 stops16h 55m
Southwest
Deal found 4/26![Southwest logo]()
$515
This Kissandfly.com deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kissandfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/2612:27 pm
COS
- SXM
2 stops22h 48m
British Airways
Sat 10/102:35 pm
SXM
- COS
2 stops23h 02m
British Airways
Deal found 4/27![British Airways logo]()
$606
This American Airlines deal was found by Cheapflights users on 4/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/93:45 pm
COS
- MBJ
2 stops19h 02m
American Airlines
Thu 7/1612:47 pm
MBJ
- COS
1 stop10h 37m
American Airlines
Deal found 4/25![American Airlines logo]()
$467
This Delta deal was found by Cheapflights users on 4/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/96:00 am
COS
- NAS
1 stop8h 37m
Delta
Tue 6/163:29 pm
NAS
- COS
1 stop7h 38m
Delta
Deal found 4/25![Delta logo]()
$498
This American Airlines deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
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 4/27![American Airlines logo]()
$496
This Delta deal was found by Cheapflights users on 4/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/196:00 am
COS
- NAS
1 stop5h 49m
Delta
Sat 10/243:15 pm
NAS
- COS
1 stop8h 06m
Delta
Deal found 4/26![Delta logo]()
$498
This United Airlines deal was found by Cheapflights users on 4/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/97:30 am
COS
- NAS
1 stop6h 26m
United Airlines
Tue 6/164:58 pm
NAS
- COS
2 stops17h 43m
United Airlines
Deal found 4/25![United Airlines logo]()
$571
This Southwest deal was found by Cheapflights users on 4/28. 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 6/269:35 am
COS
- SJU
1 stop12h 50m
Southwest
Tue 6/309:50 am
SJU
- COS
2 stops9h 45m
Southwest
Deal found 4/28![Southwest logo]()
$587
This American Airlines deal was found by Cheapflights users on 4/24. 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 10/35:13 pm
COS
- PUJ
2 stops19h 22m
American Airlines
Sun 10/115:20 pm
PUJ
- COS
2 stops20h 17m
American Airlines
Deal found 4/24![American Airlines logo]()
$496
This United Airlines deal was found by Cheapflights users on 4/28. 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 9/1512:45 pm
COS
- SJU
1 stop23h 59m
United Airlines
Tue 10/132:00 pm
SJU
- COS
1 stop10h 03m
United Airlines
Deal found 4/28![United Airlines logo]()
$593
This Southwest deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/155:00 am
COS
- SJU
2 stops13h 00m
Southwest
Fri 5/226:50 am
SJU
- COS
2 stops16h 55m
Southwest
Deal found 4/27![Southwest logo]()
$603
This Delta deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/66:00 am
COS
- NAS
1 stop5h 49m
Delta
Tue 10/131:16 pm
NAS
- COS
1 stop10h 05m
Delta
Deal found 4/27![Delta logo]()
$555
This American Airlines deal was found by Cheapflights users on 4/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/95:15 pm
COS
- MBJ
2 stops18h 53m
American Airlines
Tue 6/165:17 pm
MBJ
- COS
2 stops22h 45m
American Airlines
Deal found 4/25![American Airlines logo]()
$522
This United Airlines deal was found by Cheapflights users on 4/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/246:00 am
COS
- PUJ
1 stop9h 35m
United Airlines
Sat 10/311:05 pm
PUJ
- COS
1 stop12h 54m
United Airlines
Deal found 4/25![United Airlines logo]()
$606
This Southwest deal was found by Cheapflights users on 4/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/2610:25 am
COS
- SJU
2 stops11h 15m
Southwest
Tue 6/28:10 am
SJU
- COS
2 stops14h 05m
Southwest
Deal found 4/26![Southwest logo]()
$618
This Delta deal was found by Cheapflights users on 4/29. 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 8/166:00 am
COS
- SJU
1 stop8h 35m
Delta
Sun 8/231:06 pm
SJU
- COS
1 stop10h 09m
Delta
Deal found 4/29![Delta logo]()
$568
This United Airlines deal was found by Cheapflights users on 4/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/236:31 pm
COS
- PUJ
2 stops18h 59m
United Airlines
Tue 10/271:05 pm
PUJ
- COS
1 stop9h 51m
United Airlines
Deal found 4/25![United Airlines logo]()
$611
This Southwest deal was found by Cheapflights users on 4/28. 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 6/1610:35 am
COS
- SJU
1 stop12h 10m
Southwest
Tue 6/2312:20 pm
SJU
- COS
2 stops11h 25m
Southwest
Deal found 4/28![Southwest logo]()
$618
This American Airlines deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/28:00 am
COS
- NAS
1 stop7h 05m
American Airlines
Sat 8/86:24 pm
NAS
- COS
2 stops16h 54m
American Airlines
Deal found 4/27![American Airlines logo]()
$589
This United Airlines deal was found by Cheapflights users on 4/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/236:31 pm
COS
- PUJ
2 stops18h 59m
United Airlines
Wed 10/281:55 pm
PUJ
- COS
1 stop9h 45m
United Airlines
Deal found 4/25![United Airlines logo]()
$611
This Delta deal was found by Cheapflights users on 4/28. 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 9/16:00 am
COS
- SJU
1 stop8h 35m
Delta
Wed 9/232:26 pm
SJU
- COS
1 stop8h 49m
Delta
Deal found 4/28![Delta logo]()
$626
This Southwest deal was found by Cheapflights users on 4/28. 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 6/177:55 pm
COS
- MBJ
2 stops16h 25m
Southwest
Wed 6/2411:45 am
MBJ
- COS
2 stops11h 00m
Southwest
Deal found 4/28![Southwest logo]()
$642
This American Airlines deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/253:45 pm
COS
- PUJ
2 stops19h 07m
American Airlines
Wed 7/295:04 pm
PUJ
- COS
1 stop18h 49m
American Airlines
Deal found 4/27![American Airlines logo]()
$598
This United Airlines deal was found by Cheapflights users on 4/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/191:15 pm
COS
- NAS
2 stops22h 18m
United Airlines
Sat 10/242:53 pm
NAS
- COS
1 stop8h 29m
United Airlines
Deal found 4/26![United Airlines logo]()
$612
This Delta deal was found by Cheapflights users on 4/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/156:20 pm
COS
- SJU
2 stops15h 40m
Delta
Tue 6/2312:54 pm
SJU
- COS
1 stop10h 13m
Delta
Deal found 4/26![Delta logo]()
$626
This United Airlines deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/1112:56 pm
COS
- SXM
2 stops21h 37m
United Airlines
Thu 6/183:50 pm
SXM
- COS
2 stops18h 51m
United Airlines
Deal found 4/27![United Airlines logo]()
$616
This Delta deal was found by Cheapflights users on 4/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/106:00 am
COS
- NAS
1 stop5h 49m
Delta
Mon 9/143:14 pm
NAS
- COS
1 stop8h 01m
Delta
Deal found 4/24![Delta logo]()
$652
Last-minute flights from Colorado Springs to CaribbeanDiscover last-minute flight deals from Colorado Springs to Caribbean. Data last updated April 29, 2026 and is based on user searches.
Discover last-minute flight deals from Colorado Springs to Caribbean. Data last updated April 29, 2026 and is based on user searches.
This Delta deal was found by Cheapflights users on 4/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/26:15 am
COS
- SJU
1 stop8h 08m
Delta
Sat 5/91:14 pm
SJU
- COS
1 stop10h 13m
Delta
Deal found 4/26![Delta logo]()
$478
This Southwest deal was found by Cheapflights users on 4/28. 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 5/26:20 am
COS
- SJU
1 stop7h 15m
Southwest
Mon 5/410:00 am
SJU
- COS
2 stops14h 15m
Southwest
Deal found 4/28![Southwest logo]()
$560
This American Airlines deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/612:22 pm
COS
- STT
2 stops21h 13m
American Airlines
Wed 5/135:05 pm
STT
- COS
2 stops18h 22m
American Airlines
Deal found 4/27![American Airlines logo]()
$480
This United Airlines deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/66:57 pm
COS
- STT
2 stops16h 11m
United Airlines
Wed 5/131:22 pm
STT
- COS
1 stop10h 09m
United Airlines
Deal found 4/27![United Airlines logo]()
$528
This American Airlines deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/75:40 am
COS
- SJU
2 stops10h 30m
American Airlines
Mon 5/1111:59 pm
SJU
- COS
1 stop11h 28m
American Airlines
Deal found 4/27![American Airlines logo]()
$518
This Southwest deal was found by Cheapflights users on 4/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/118:00 pm
COS
- SJU
2 stops12h 35m
Southwest
Fri 5/156:50 am
SJU
- COS
2 stops16h 55m
Southwest
Deal found 4/26![Southwest logo]()
$515
This Delta deal was found by Cheapflights users on 4/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/136:00 am
COS
- SDQ
2 stops16h 38m
Delta
Fri 7/37:35 pm
SDQ
- COS
2 stops16h 55m
Delta
Deal found 4/26![Delta logo]()
$547
This American Airlines deal was found by Cheapflights users on 4/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/145:13 pm
COS
- MBJ
2 stops19h 12m
American Airlines
Tue 5/2612:31 pm
MBJ
- COS
2 stops22h 23m
American Airlines
Deal found 4/26![American Airlines logo]()
$447
This American Airlines deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/155:13 pm
COS
- SJU
1 stop9h 19m
American Airlines
Thu 5/2112:44 am
SJU
- COS
1 stop11h 10m
American Airlines
Deal found 4/27![American Airlines logo]()
$565
This American Airlines deal was found by Cheapflights users on 4/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/181:39 pm
COS
- SJU
2 stops17h 34m
American Airlines
Wed 6/37:15 pm
SJU
- COS
2 stops16h 38m
American Airlines
Deal found 4/26![American Airlines logo]()
$456
This Delta deal was found by Cheapflights users on 4/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/196:00 am
COS
- SDQ
2 stops16h 38m
Delta
Fri 7/37:35 pm
SDQ
- COS
2 stops16h 55m
Delta
Deal found 4/26![Delta logo]()
$491
This American Airlines deal was found by Cheapflights users on 4/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/233:45 pm
COS
- PUJ
2 stops17h 10m
American Airlines
Wed 5/271:52 pm
PUJ
- COS
2 stops22h 02m
American Airlines
Deal found 4/26![American Airlines logo]()
$541
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 April 29, 2026.
Search for one-way flight options from Colorado Springs to Caribbean. Find affordable one-way fares based on user searches. Data last updated April 29, 2026.
This United Airlines deal was found by Cheapflights users on 4/28. 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 8/155:30 am
COS
- SJU
1 stop10h 08m
United Airlines
Deal found 4/28![United Airlines logo]()
$150
This American Airlines deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/313:51 pm
COS
- SJU
2 stops18h 57m
American Airlines
Deal found 4/27![American Airlines logo]()
$171
This American Airlines deal was found by Cheapflights users on 4/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/213:40 pm
COS
- STT
2 stops19h 10m
American Airlines
Deal found 4/25![American Airlines logo]()
$192
This Kiwi.com deal was found by Cheapflights users on 4/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/1510:39 am
COS
- SDQ
2 stops30h 39m
Multiple Airlines
Deal found 4/26![Multiple Airlines logo]()
$201
This Delta deal was found by Cheapflights users on 4/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/196:00 am
COS
- SDQ
2 stops16h 38m
Delta
Deal found 4/26![Delta logo]()
$231
This Kiwi.com deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/1910:06 am
COS
- SJU
2 stops27h 52m
Multiple Airlines
Deal found 4/28![Multiple Airlines logo]()
$247
This Delta deal was found by Cheapflights users on 4/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/316:00 am
COS
- SJU
1 stop8h 35m
Delta
Deal found 4/26![Delta logo]()
$280
This Delta deal was found by Cheapflights users on 4/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/1111:55 am
COS
- SDQ
2 stops22h 33m
Delta
Deal found 4/26![Delta logo]()
$287
This Delta deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/1111:55 am
COS
- PUJ
2 stops22h 28m
Delta
Deal found 4/27![Delta logo]()
$287
This Delta deal was found by Cheapflights users on 4/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/168:15 am
COS
- SDQ
2 stops26h 13m
Delta
Deal found 4/26![Delta logo]()
$293
This United Airlines deal was found by Cheapflights users on 4/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/186:57 pm
COS
- SDQ
2 stops25h 49m
United Airlines
Deal found 4/26![United Airlines logo]()
$297
This Delta deal was found by Cheapflights users on 4/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/216:00 am
COS
- STT
1 stop7h 20m
Delta
Deal found 4/25![Delta logo]()
$301
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 April 29, 2026.
Round-trip from | $322 (United Airlines) |
|---|---|
One-way from | $150 (United Airlines) |
Popular in | March |
Cheapest in | January |
Average price | $448 |
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 April 29, 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
Tue 9/1
5:30 am-8:38 pm
2 stops13h 08m
San Juan Luis Munoz Marin Intl
Tue 9/22
1:00 am-10:59 am
2 stops11h 59m
$322
Colorado SpringsMontego Bay
COS - MBJ
COSMBJ
Colorado Springs
Thu 5/14
5:13 pm-1:25 pm
2 stops19h 12m
Montego Bay Sangster Intl
Tue 5/26
12:31 pm-9:54 am
2 stops22h 23m
$447
Colorado SpringsMontego Bay
COS - MBJ
COSMBJ
Colorado Springs
Thu 7/9
3:45 pm-11:47 am
2 stops19h 02m
Montego Bay Sangster Intl
Thu 7/16
12:47 pm-10:24 pm
1 stop10h 37m
$467
Colorado SpringsSanto Domingo
COS - SDQ
COSSDQ
Colorado Springs
Tue 5/19
6:00 am-12:38 am
2 stops16h 38m
Santo Domingo Las Americas
Fri 7/3
7:35 pm-10:30 am
2 stops16h 55m
$491
Colorado SpringsPunta Cana
COS - PUJ
COSPUJ
Colorado Springs
Thu 9/17
3:51 pm-2:35 pm
2 stops20h 44m
Punta Cana
Sun 9/20
3:10 pm-9:25 am
2 stops20h 15m
$496
Colorado SpringsPunta Cana
COS - PUJ
COSPUJ
Colorado Springs
Sat 10/3
5:13 pm-2:35 pm
2 stops19h 22m
Punta Cana
Sun 10/11
5:20 pm-11:37 am
2 stops20h 17m
$496
Colorado SpringsNassau
COS - NAS
COSNAS
Colorado Springs
Tue 6/9
6:00 am-4:37 pm
1 stop8h 37m
Nassau Intl
Tue 6/16
3:29 pm-9:07 pm
1 stop7h 38m
$498
Colorado SpringsNassau
COS - NAS
COSNAS
Colorado Springs
Mon 10/19
6:00 am-1:49 pm
1 stop5h 49m
Nassau Intl
Sat 10/24
3:15 pm-9:21 pm
1 stop8h 06m
$498
Colorado SpringsSan Juan
COS - SJU
COSSJU
Colorado Springs
Mon 5/11
8:00 pm-10:35 am
2 stops12h 35m
San Juan Luis Munoz Marin Intl
Fri 5/15
6:50 am-9:45 pm
2 stops16h 55m
$515
Colorado SpringsMontego Bay
COS - MBJ
COSMBJ
Colorado Springs
Tue 6/9
5:15 pm-1:08 pm
2 stops18h 53m
Montego Bay Sangster Intl
Tue 6/16
5:17 pm-3:02 pm
2 stops22h 45m
$522
Showing 1-10 of 51 resultsSorted by cheapest first
Best time to book a flight from Colorado Springs to Caribbean
Have a flexible travel schedule? Discover the best time to fly to Caribbean from Colorado Springs with our price prediction graph.
COS-SJU
COS-MBJ
COS-STT
COS-SDQ
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-MBJ
COS-STT
COS-SDQ
What is the cheapest month to book a flight from Colorado Springs to Caribbean?
Currently, July 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 June is currently the most expensive (average of $529). 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 April 29, 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.
Comfort
8.0
Entertainment
7.5
Food
7.0
Overall
8.0
Boarding
8.1
Crew
8.6
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Comfort
8.0
Entertainment
7.5
Food
7.0
Overall
8.0
Boarding
8.1
Crew
8.6
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Comfort
8.0
Entertainment
7.5
Food
7.0
Overall
8.0
Boarding
8.1
Crew
8.6
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Comfort
8.0
Entertainment
7.5
Food
7.0
Overall
8.0
Boarding
8.1
Crew
8.6
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Comfort
8.0
Entertainment
7.5
Food
7.0
Overall
8.0
Boarding
8.1
Crew
8.6
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 April 29, 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 April 29, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$192 | Average$376 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$272 | Average$721 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$339 | Average$588 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$380 | Average$639 | FlexibilityNo cancel fee | On-time63% |