$118+ Cheap flights from New Haven (HVN) to Caribbean
This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 9/28. Fares are subject to change and may not be available on all flights or dates of travel.
HVN — SJU
Oct 14 — Oct 211
Round-trip
1 adult, Economy
We work with more than 300 partners to bring you better travel deals
Find cheap flights from New Haven to Caribbean with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheap flight deals from New Haven to Caribbean
Cheapest
Best
Last-minute
One-way
Cheapest flights from New Haven to CaribbeanExplore the most affordable flight options available from New Haven to Caribbean. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 14, 2026.
Explore the most affordable flight options available from New Haven to Caribbean. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 14, 2026.
This CheapOair deal was found by Cheapflights users on 9/10. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/308:30 am -
Nonstop3h 44m
Fri 12/42:55 pm -
Nonstop4h 12m
Deal found 9/10![Avelo Airlines logo]()
$231
This Expedia deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/97:00 am -
Nonstop3h 57m
Fri 11/131:08 pm -
Nonstop4h 07m
Deal found 9/9![Avelo Airlines logo]()
$245
This Super.com deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/217:00 am -
Nonstop3h 57m
Fri 9/2512:08 pm -
Nonstop4h 07m
Deal found 9/9![Avelo Airlines logo]()
$247
This CheapOair deal was found by Cheapflights users on 9/10. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/192:10 pm -
Nonstop3h 50m
Sat 9/267:00 pm -
Nonstop3h 57m
Deal found 9/10![Avelo Airlines logo]()
$251
This CheapOair deal was found by Cheapflights users on 9/12. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/287:00 am -
Nonstop3h 57m
Fri 10/212:08 pm -
Nonstop4h 07m
Deal found 9/12![Avelo Airlines logo]()
$253
This CheapOair deal was found by Cheapflights users on 9/10. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/142:10 pm -
Nonstop3h 50m
Sat 11/213:33 am -
Nonstop4h 12m
Deal found 9/10![Avelo Airlines logo]()
$256
This eDestinos deal was found by Cheapflights users on 9/13. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/172:10 pm -
Nonstop3h 50m
Wed 10/217:00 pm -
Nonstop3h 57m
Deal found 9/13![Avelo Airlines logo]()
$261
This CheapOair deal was found by Cheapflights users on 9/10. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/312:10 pm -
Nonstop3h 50m
Sat 11/78:00 pm -
Nonstop3h 57m
Deal found 9/10![Avelo Airlines logo]()
$266
This CheapOair deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/72:10 pm -
Nonstop3h 50m
Mon 11/91:08 pm -
Nonstop4h 07m
Deal found 9/9![Avelo Airlines logo]()
$270
This CheapOair deal was found by Cheapflights users on 9/10. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/208:30 am -
Nonstop3h 44m
Sat 11/213:33 am -
Nonstop4h 12m
Deal found 9/10![Avelo Airlines logo]()
$271
This CheapOair deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/192:10 pm -
Nonstop3h 50m
Wed 9/237:00 pm -
Nonstop3h 57m
Deal found 9/9![Avelo Airlines logo]()
$275
This CheapOair deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/232:10 pm -
Nonstop3h 50m
Fri 10/212:08 pm -
Nonstop4h 07m
Deal found 9/9![Avelo Airlines logo]()
$277
Best flights from New Haven to CaribbeanDiscover carefully curated flight deals from New Haven to Caribbean that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 14, 2026.
Discover carefully curated flight deals from New Haven to Caribbean that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 14, 2026.
This CheapOair deal was found by Cheapflights users on 9/11. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/312:10 pm -
Nonstop3h 50m
Sat 11/78:00 pm -
Nonstop3h 57m
Deal found 9/11![Avelo Airlines logo]()
$266
This WAYA deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure WAYA is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/242:10 pm -
1 stop7h 51m
Sat 10/312:21 pm -
1 stop8h 36m
Deal found 9/9![Multiple Airlines logo]()
$536
This CheapOair deal was found by Cheapflights users on 9/10. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/208:30 am -
Nonstop3h 44m
Sat 11/213:33 am -
Nonstop4h 12m
Deal found 9/10![Avelo Airlines logo]()
$271
This CheapOair deal was found by Cheapflights users on 9/13. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/167:00 am -
Nonstop3h 57m
Mon 11/232:14 pm -
Nonstop4h 11m
Deal found 9/13![Avelo Airlines logo]()
$302
This CheapOair deal was found by Cheapflights users on 9/10. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/67:00 am -
Nonstop3h 57m
Mon 11/91:08 pm -
Nonstop4h 07m
Deal found 9/10![Avelo Airlines logo]()
$310
This CheapOair deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/307:00 am -
Nonstop3h 57m
Mon 11/21:08 pm -
Nonstop4h 07m
Deal found 9/9![Avelo Airlines logo]()
$310
This Expedia deal was found by Cheapflights users on 9/12. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/112:10 pm -
Nonstop3h 50m
Mon 11/161:08 pm -
Nonstop4h 07m
Deal found 9/12![Avelo Airlines logo]()
$330
This CheapOair deal was found by Cheapflights users on 9/13. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 1/298:30 am -
Nonstop4h 01m
Fri 2/52:35 pm -
Nonstop4h 15m
Deal found 9/13![Avelo Airlines logo]()
$336
This CheapOair deal was found by Cheapflights users on 9/13. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/237:00 am -
Nonstop3h 57m
Mon 10/2612:08 pm -
Nonstop4h 07m
Deal found 9/13![Avelo Airlines logo]()
$338
This Mytrip deal was found by Cheapflights users on 9/12. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/2811:15 am -
2 stops33h 25m
Wed 11/43:30 pm -
2 stops31h 39m
Deal found 9/12![Multiple Airlines logo]()
$618
This KAYAK deal was found by Cheapflights users on 9/11. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/246:34 pm -
2 stops13h 56m
Sun 9/2710:20 am -
2 stops24h 03m
Deal found 9/11![Breeze Airways logo]()
$1,257
This Expedia deal was found by Cheapflights users on 9/12. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 1/206:30 am -
Nonstop4h 01m
Mon 1/252:35 pm -
Nonstop4h 15m
Deal found 9/12![Avelo Airlines logo]()
$345
This Mytrip deal was found by Cheapflights users on 9/10. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/255:15 pm -
2 stops24h 05m
Sun 11/12:20 pm -
2 stops32h 19m
Deal found 9/10![Multiple Airlines logo]()
$664
This CheapOair deal was found by Cheapflights users on 9/11. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/238:30 am -
Nonstop3h 44m
Mon 11/302:14 pm -
Nonstop4h 11m
Deal found 9/11![Avelo Airlines logo]()
$346
This Mytrip deal was found by Cheapflights users on 9/12. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/264:00 pm -
2 stops19h 30m
Mon 11/212:30 pm -
2 stops24h 39m
Deal found 9/12![Multiple Airlines logo]()
$671
This Mytrip deal was found by Cheapflights users on 9/12. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/186:09 pm -
2 stops23h 21m
Wed 9/2312:00 pm -
1 stop9h 57m
Deal found 9/12![Multiple Airlines logo]()
$677
This Booking.com deal was found by Cheapflights users on 9/10. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/58:00 am -
2 stops29h 15m
Sat 12/1211:25 am -
3 stops25h 16m
Deal found 9/10![Multiple Airlines logo]()
$826
This Mytrip deal was found by Cheapflights users on 9/13. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/307:00 am -
1 stop12h 20m
Mon 11/28:39 am -
1 stop8h 36m
Deal found 9/13![Multiple Airlines logo]()
$839
This Mytrip deal was found by Cheapflights users on 9/13. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/287:00 am -
1 stop6h 21m
Fri 10/28:39 am -
1 stop7h 36m
Deal found 9/13![Multiple Airlines logo]()
$841
This Mytrip deal was found by Cheapflights users on 9/12. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/267:30 am -
3 stops28h 50m
Wed 10/712:30 pm -
2 stops33h 29m
Deal found 9/12![Multiple Airlines logo]()
$918
This Mytrip deal was found by Cheapflights users on 9/12. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/32:25 pm -
2 stops23h 55m
Tue 10/66:45 pm -
2 stops27h 12m
Deal found 9/12![Multiple Airlines logo]()
$968
This Mytrip deal was found by Cheapflights users on 9/12. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/286:30 am -
2 stops30h 20m
Wed 11/41:50 pm -
2 stops32h 19m
Deal found 9/12![Multiple Airlines logo]()
$976
This KAYAK deal was found by Cheapflights users on 9/13. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/126:24 pm -
2 stops18h 21m
Sat 2/201:45 pm -
2 stops27h 17m
Deal found 9/13![Breeze Airways logo]()
$2,500
This Mytrip deal was found by Cheapflights users on 9/12. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/197:00 am -
3 stops30h 25m
Fri 12/42:20 pm -
2 stops25h 10m
Deal found 9/12![Multiple Airlines logo]()
$986
This Mytrip deal was found by Cheapflights users on 9/11. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/318:30 am -
2 stops29h 05m
Sat 1/167:45 pm -
2 stops27h 31m
Deal found 9/11![Multiple Airlines logo]()
$1,006
This Mytrip deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/249:35 am -
2 stops29h 20m
Mon 9/289:10 am -
3 stops26h 59m
Deal found 9/9![Multiple Airlines logo]()
$1,167
This Kiwi.com deal was found by Cheapflights users on 9/13. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/126:24 pm -
1 stop17h 01m
Sat 2/206:55 pm -
2 stops25h 19m
Deal found 9/13![Multiple Airlines logo]()
$1,337
Last-minute flights from New Haven to CaribbeanDiscover last-minute flight deals from New Haven to Caribbean. Data last updated September 14, 2026 and is based on user searches.
Discover last-minute flight deals from New Haven to Caribbean. Data last updated September 14, 2026 and is based on user searches.
This CheapOair deal was found by Cheapflights users on 9/10. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/192:10 pm -
Nonstop3h 50m
Sat 9/267:00 pm -
Nonstop3h 57m
Deal found 9/10![Avelo Airlines logo]()
$251
This CheapOair deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/192:10 pm -
Nonstop3h 50m
Wed 9/237:00 pm -
Nonstop3h 57m
Deal found 9/9![Avelo Airlines logo]()
$275
This Super.com deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/217:00 am -
Nonstop3h 57m
Fri 9/2512:08 pm -
Nonstop4h 07m
Deal found 9/9![Avelo Airlines logo]()
$247
This CheapOair deal was found by Cheapflights users on 9/13. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/217:00 am -
Nonstop3h 57m
Sat 9/267:00 pm -
Nonstop3h 57m
Deal found 9/13![Avelo Airlines logo]()
$282
This CheapOair deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/232:10 pm -
Nonstop3h 50m
Fri 10/212:08 pm -
Nonstop4h 07m
Deal found 9/9![Avelo Airlines logo]()
$277
This CheapOair deal was found by Cheapflights users on 9/12. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/287:00 am -
Nonstop3h 57m
Fri 10/212:08 pm -
Nonstop4h 07m
Deal found 9/12![Avelo Airlines logo]()
$253
This CheapOair deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/32:10 pm -
Nonstop3h 50m
Wed 10/77:00 pm -
Nonstop3h 57m
Deal found 9/9![Avelo Airlines logo]()
$283
This eDestinos deal was found by Cheapflights users on 9/13. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/172:10 pm -
Nonstop3h 50m
Wed 10/217:00 pm -
Nonstop3h 57m
Deal found 9/13![Avelo Airlines logo]()
$261
This CheapOair deal was found by Cheapflights users on 9/10. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/172:10 pm -
Nonstop3h 50m
Sat 10/247:00 pm -
Nonstop3h 57m
Deal found 9/10![Avelo Airlines logo]()
$285
This CheapOair deal was found by Cheapflights users on 9/13. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/282:10 pm -
Nonstop3h 50m
Mon 11/21:08 pm -
Nonstop4h 07m
Deal found 9/13![Avelo Airlines logo]()
$290
This Expedia deal was found by Cheapflights users on 9/13. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/307:00 am -
Nonstop3h 57m
Mon 11/21:08 pm -
Nonstop4h 07m
Deal found 9/13![Avelo Airlines logo]()
$278
This CheapOair deal was found by Cheapflights users on 9/10. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/312:10 pm -
Nonstop3h 50m
Sat 11/78:00 pm -
Nonstop3h 57m
Deal found 9/10![Avelo Airlines logo]()
$266
One-way flights from New Haven to CaribbeanSearch for one-way flight options from New Haven to Caribbean. Find affordable one-way fares based on user searches. Data last updated September 14, 2026.
Search for one-way flight options from New Haven to Caribbean. Find affordable one-way fares based on user searches. Data last updated September 14, 2026.
This CheapOair deal was found by Cheapflights users on 9/11. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/287:00 am -
Nonstop3h 57m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/11![Avelo Airlines logo]()
$118
This Super.com deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/307:00 am -
Nonstop3h 57m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/9![Avelo Airlines logo]()
$128
This CheapOair deal was found by Cheapflights users on 9/10. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/142:10 pm -
Nonstop3h 50m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/10![Avelo Airlines logo]()
$130
This CheapOair deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/288:59 pm -
Nonstop3h 45m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/9![Avelo Airlines logo]()
$132
This eDestinos deal was found by Cheapflights users on 9/13. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/217:00 am -
Nonstop3h 57m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/13![Avelo Airlines logo]()
$135
This CheapOair deal was found by Cheapflights users on 9/10. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/167:00 am -
Nonstop3h 57m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/10![Avelo Airlines logo]()
$138
This CheapOair deal was found by Cheapflights users on 9/11. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/142:10 pm -
Nonstop3h 50m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/11![Avelo Airlines logo]()
$139
This CheapOair deal was found by Cheapflights users on 9/10. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/262:10 pm -
Nonstop3h 50m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/10![Avelo Airlines logo]()
$141
This CheapOair deal was found by Cheapflights users on 9/10. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/192:10 pm -
Nonstop3h 50m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/10![Avelo Airlines logo]()
$142
This CheapOair deal was found by Cheapflights users on 9/10. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/238:30 am -
Nonstop3h 44m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/10![Avelo Airlines logo]()
$145
This CheapOair deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/302:10 pm -
Nonstop3h 50m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/9![Avelo Airlines logo]()
$146
This CheapOair deal was found by Cheapflights users on 9/12. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/42:10 pm -
Nonstop3h 50m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/12![Avelo Airlines logo]()
$147
Find flight deals from New Haven to Caribbean
Keep the following information in mind while searching for New Haven to Caribbean flight deals. Data was last updated September 14, 2026.
Round-trip from | $231 (CheapOair) |
|---|---|
One-way from | $118 (CheapOair) |
Popular in | July |
Cheapest in | October |
Average price | $299 |
Good round-trip deal | $259 or less |
Good one-way deal | $160 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from New Haven to Caribbean that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 7,457,451 searches. Data last updated September 14, 2026.
Use the filters below to find and compare flights from New Haven to Caribbean that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
New HavenSan Juan
HVN Tweed-New Haven - SJU San Juan Luis Munoz Marin Intl
HVNSJU
Tweed-New Haven
Mon 9/28
7:00 am-10:57 am
Nonstop3h 57m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$118
New HavenSan Juan
HVN Tweed-New Haven - SJU San Juan Luis Munoz Marin Intl
HVNSJU
Tweed-New Haven
Fri 10/30
7:00 am-10:57 am
Nonstop3h 57m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$128
Quickest round-trip
New HavenSan Juan
HVN Tweed-New Haven - SJU San Juan Luis Munoz Marin Intl
HVNSJU
Tweed-New Haven
Sat 11/28
8:59 pm-1:44 am
Nonstop3h 45m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$130
New HavenSan Juan
HVN Tweed-New Haven - SJU San Juan Luis Munoz Marin Intl
HVNSJU
Tweed-New Haven
Wed 11/11
2:10 pm-7:00 pm
Nonstop3h 50m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$130
New HavenSan Juan
HVN Tweed-New Haven - SJU San Juan Luis Munoz Marin Intl
HVNSJU
Tweed-New Haven
Mon 11/16
7:00 am-11:57 am
Nonstop3h 57m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$138
New HavenSan Juan
HVN Tweed-New Haven - SJU San Juan Luis Munoz Marin Intl
HVNSJU
Tweed-New Haven
Wed 10/14
2:10 pm-6:00 pm
Nonstop3h 50m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$139
New HavenSan Juan
HVN Tweed-New Haven - SJU San Juan Luis Munoz Marin Intl
HVNSJU
Tweed-New Haven
Sat 10/31
2:10 pm-6:00 pm
Nonstop3h 50m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$141
New HavenSan Juan
HVN Tweed-New Haven - SJU San Juan Luis Munoz Marin Intl
HVNSJU
Tweed-New Haven
Mon 10/26
7:00 am-10:57 am
Nonstop3h 57m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$141
New HavenSan Juan
HVN Tweed-New Haven - SJU San Juan Luis Munoz Marin Intl
HVNSJU
Tweed-New Haven
Wed 9/23
2:10 pm-6:00 pm
Nonstop3h 50m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$142
New HavenSan Juan
HVN Tweed-New Haven - SJU San Juan Luis Munoz Marin Intl
HVNSJU
Tweed-New Haven
Wed 9/30
2:10 pm-6:00 pm
Nonstop3h 50m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$146
Showing 1-10 of 39 resultsSorted by cheapest first
Best time to book a flight from New Haven to Caribbean
Have a flexible travel schedule? Discover the best time to fly to Caribbean from New Haven with our price prediction graph.
HVN-SJU
HVN-PUJ
HVN-NAS
HVN-MBJ
HVN-STT
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 New Haven to Caribbean
HVN-0CB
HVN-SJU
HVN-PUJ
HVN-NAS
HVN-MBJ
What is the cheapest month to book a flight from New Haven to Caribbean?
Currently, September is the cheapest month in which you can book a flight from New Haven to Caribbean (average of $187). Flying from New Haven to Caribbean in December is currently the most expensive (average of $650). 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.
What is the cheapest time of day to fly from HVN to CB?
Find hourly flight availability from New Haven to Caribbean. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated September 14, 2026.
Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from New Haven to Caribbean as you normally would.
How far ahead should I book a flight from New Haven to Caribbean?
The best time to book flights from New Haven to Caribbean is 29 days before your desired departure date. The cost of your flight will likely increase significantly if you book two weeks in advance of your flight.
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 September 14, 2026.
Get a feel of what it's like to fly with Avelo Airlines,JetBlue, andFrontier from New Haven 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.
Avelo Airlines
Entertainment
5.0
Comfort
7.1
Overall
7.5
Food
5.1
Boarding
7.7
Crew
8.2
Reviews
1 / 7
8.0
ExcellentAnonymous,Dec 2025
USA - ROC
Avelo Airlines
Avelo Airlines
Entertainment
5.0
Comfort
7.1
Overall
7.5
Food
5.1
Boarding
7.7
Crew
8.2
Reviews
1 / 7
8.0
ExcellentAnonymous,Dec 2025
USA - ROC
Avelo Airlines
Entertainment
5.0
Comfort
7.1
Overall
7.5
Food
5.1
Boarding
7.7
Crew
8.2
Reviews
1 / 7
8.0
ExcellentAnonymous,Dec 2025
USA - ROC
Avelo Airlines
Entertainment
5.0
Comfort
7.1
Overall
7.5
Food
5.1
Boarding
7.7
Crew
8.2
Reviews
1 / 7
8.0
ExcellentAnonymous,Dec 2025
USA - ROC
Related info for your journey
Find useful and relevant information for your journey from New Haven to Caribbean. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Browse thousands of different options on Cheapflights for your next trip
Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
Alternative routes
Complete your trip
Flights by cabin class
Other flight options
Popular flights
Top countries
Top destinations
Alternative routes for New Haven 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 New Haven to Caribbean by cabin class
Find flights from New Haven to Caribbean, based on your preferred cabin class, be it economy, premium economy, business, or first class.
New Haven and Caribbean flights
Browse other New Haven and Caribbean flight options. Last updated on September 14, 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.
New Haven to Caribbean flights
Consider these flights traveling from New Haven to Caribbean.
Top 3 airlines flying from New Haven to Caribbean
Discover the top 3 airlines that operate flights from New Haven to Caribbean. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 7,457,451 searches. Data last updated September 14, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$89 | Average$324 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$155 | Average$329 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$207 | Average$367 | FlexibilityNo cancel fee | On-time62% |