$685+ Cheap flights to Leeward Islands
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 5/8. Fares are subject to change and may not be available on all flights or dates of travel.
— BOB
May 17 — May 241
Round-trip
1 adult, Economy
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Best
Last-minute
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Cheapest flights to Leeward IslandsExplore the most affordable flight options available to Leeward Islands. Find the lowest fares based on data from user searches, with prices last updated on April 17, 2026.
Explore the most affordable flight options available to Leeward Islands. Find the lowest fares based on data from user searches, with prices last updated on April 17, 2026.
This Justfly.com deal was found by Cheapflights users on 4/12. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/267:59 am
EWR
- BOB
2 stops30h 51m
Multiple Airlines
Sun 5/37:40 pm
BOB
- EWR
2 stops28h 23m
Multiple Airlines
Deal found 4/12![Multiple Airlines logo]()
$1,211
This FlightHub deal was found by Cheapflights users on 4/14. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/297:59 am
EWR
- BOB
2 stops30h 11m
Multiple Airlines
Wed 5/66:20 pm
BOB
- EWR
2 stops29h 43m
Multiple Airlines
Deal found 4/14![Multiple Airlines logo]()
$1,283
This FlightHub deal was found by Cheapflights users on 4/14. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/17:59 am
EWR
- BOB
2 stops32h 16m
Multiple Airlines
Wed 5/67:35 pm
BOB
- EWR
2 stops28h 28m
Multiple Airlines
Deal found 4/14![Multiple Airlines logo]()
$1,328
This FlightHub deal was found by Cheapflights users on 4/13. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/67:59 am
EWR
- BOB
2 stops30h 21m
Multiple Airlines
Wed 5/137:10 pm
BOB
- EWR
2 stops37h 31m
Multiple Airlines
Deal found 4/13![Multiple Airlines logo]()
$1,336
This FlightHub deal was found by Cheapflights users on 4/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/65:28 pm
JFK
- BOB
2 stops22h 42m
Multiple Airlines
Wed 5/137:10 pm
BOB
- JFK
2 stops30h 27m
Multiple Airlines
Deal found 4/16![Multiple Airlines logo]()
$1,417
This FlightHub deal was found by Cheapflights users on 4/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/107:59 am
EWR
- BOB
2 stops29h 56m
Multiple Airlines
Sun 5/176:55 pm
BOB
- EWR
2 stops29h 15m
Multiple Airlines
Deal found 4/16![Multiple Airlines logo]()
$1,454
This FlightHub deal was found by Cheapflights users on 4/12. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/109:30 am
JFK
- BOB
2 stops28h 35m
Multiple Airlines
Sun 6/146:20 pm
BOB
- JFK
2 stops30h 00m
Multiple Airlines
Deal found 4/12![Multiple Airlines logo]()
$1,457
This FlightHub deal was found by Cheapflights users on 4/14. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/157:50 am
EWR
- BOB
2 stops30h 20m
Multiple Airlines
Wed 4/227:10 pm
BOB
- EWR
2 stops28h 53m
Multiple Airlines
Deal found 4/14![Multiple Airlines logo]()
$1,459
This Trip.com deal was found by Cheapflights users on 4/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/238:11 pm
JFK
- BOB
2 stops49h 09m
Multiple Airlines
Sun 4/267:40 pm
BOB
- JFK
2 stops30h 19m
Multiple Airlines
Deal found 4/16![Multiple Airlines logo]()
$1,531
This FlightHub deal was found by Cheapflights users on 4/14. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/44:46 pm
JFK
- BOB
2 stops20h 54m
Multiple Airlines
Sun 9/136:25 pm
BOB
- JFK
2 stops30h 35m
Multiple Airlines
Deal found 4/14![Multiple Airlines logo]()
$1,543
This FlightHub deal was found by Cheapflights users on 4/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/179:30 am
JFK
- BOB
2 stops30h 40m
Multiple Airlines
Mon 7/67:40 pm
BOB
- JFK
2 stops28h 40m
Multiple Airlines
Deal found 4/16![Multiple Airlines logo]()
$1,549
This FlightHub deal was found by Cheapflights users on 4/12. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/89:30 am
JFK
- BOB
2 stops28h 35m
Multiple Airlines
Sun 7/126:25 pm
BOB
- JFK
2 stops29h 55m
Multiple Airlines
Deal found 4/12![Multiple Airlines logo]()
$1,631
Best flights to Leeward IslandsDiscover carefully curated flight deals to Leeward Islands that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated April 17, 2026.
Discover carefully curated flight deals to Leeward Islands that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated April 17, 2026.
This FlightHub deal was found by Cheapflights users on 4/13. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/67:59 am
EWR
- BOB
2 stops30h 21m
Multiple Airlines
Wed 5/137:10 pm
BOB
- EWR
2 stops37h 31m
Multiple Airlines
Deal found 4/13![Multiple Airlines logo]()
$1,336
This FlightHub deal was found by Cheapflights users on 4/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/65:28 pm
JFK
- BOB
2 stops22h 42m
Multiple Airlines
Wed 5/137:10 pm
BOB
- JFK
2 stops30h 27m
Multiple Airlines
Deal found 4/16![Multiple Airlines logo]()
$1,417
This FlightHub deal was found by Cheapflights users on 4/12. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/109:30 am
JFK
- BOB
2 stops28h 35m
Multiple Airlines
Sun 6/146:20 pm
BOB
- JFK
2 stops30h 00m
Multiple Airlines
Deal found 4/12![Multiple Airlines logo]()
$1,457
This FlightHub deal was found by Cheapflights users on 4/12. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/89:30 am
JFK
- BOB
2 stops28h 35m
Multiple Airlines
Sun 7/126:25 pm
BOB
- JFK
2 stops29h 55m
Multiple Airlines
Deal found 4/12![Multiple Airlines logo]()
$1,631
This lastminute.com deal was found by Cheapflights users on 4/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure lastminute.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/84:30 pm
JFK
- BOB
2 stops22h 05m
Multiple Airlines
Fri 5/297:20 pm
BOB
- JFK
2 stops21h 39m
Multiple Airlines
Deal found 4/17![Multiple Airlines logo]()
$1,686
This FlightHub deal was found by Cheapflights users on 4/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/1711:30 am
JFK
- BOB
2 stops26h 50m
Multiple Airlines
Sun 7/57:40 pm
BOB
- JFK
2 stops28h 40m
Multiple Airlines
Deal found 4/16![Multiple Airlines logo]()
$1,708
This FlightHub deal was found by Cheapflights users on 4/14. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 7/59:30 am
JFK
- BOB
2 stops28h 50m
Multiple Airlines
Sun 7/126:25 pm
BOB
- JFK
2 stops29h 55m
Multiple Airlines
Deal found 4/14![Multiple Airlines logo]()
$1,711
This FlightHub deal was found by Cheapflights users on 4/15. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/154:05 pm
JFK
- BOB
2 stops22h 00m
Multiple Airlines
Fri 5/226:40 pm
BOB
- JFK
2 stops30h 57m
Multiple Airlines
Deal found 4/15![Multiple Airlines logo]()
$1,720
This FlightHub deal was found by Cheapflights users on 4/15. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/154:30 pm
JFK
- BOB
2 stops22h 05m
Multiple Airlines
Mon 5/187:35 pm
BOB
- JFK
2 stops22h 24m
Multiple Airlines
Deal found 4/15![Multiple Airlines logo]()
$1,898
This FlightHub deal was found by Cheapflights users on 4/12. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/711:00 am
JFK
- BOB
2 stops28h 55m
Multiple Airlines
Thu 5/212:20 pm
BOB
- JFK
2 stops24h 56m
Multiple Airlines
Deal found 4/12![Multiple Airlines logo]()
$1,898
This Flighttix deal was found by Cheapflights users on 4/14. 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 Flighttix is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/303:30 pm
JFK
- BOB
2 stops23h 05m
Multiple Airlines
Sat 6/65:50 pm
BOB
- JFK
2 stops30h 10m
Multiple Airlines
Deal found 4/14![Multiple Airlines logo]()
$1,947
This Expedia deal was found by Cheapflights users on 4/15. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/57:29 pm
EWR
- BOB
2 stops42h 51m
Multiple Airlines
Wed 5/137:35 pm
BOB
- EWR
2 stops37h 58m
Multiple Airlines
Deal found 4/15![Multiple Airlines logo]()
$2,053
This Priceline deal was found by Cheapflights users on 4/13. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/287:26 pm
EWR
- BOB
2 stops43h 09m
Multiple Airlines
Thu 6/46:25 pm
BOB
- EWR
2 stops39h 08m
Multiple Airlines
Deal found 4/13![Multiple Airlines logo]()
$2,105
This Orbitz deal was found by Cheapflights users on 4/15. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/56:00 pm
EWR
- BOB
2 stops20h 35m
Multiple Airlines
Wed 9/163:20 pm
BOB
- EWR
2 stops42h 15m
Multiple Airlines
Deal found 4/15![Multiple Airlines logo]()
$2,106
This Travelocity deal was found by Cheapflights users on 4/12. 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 Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/77:29 pm
EWR
- BOB
2 stops41h 36m
Multiple Airlines
Thu 5/213:20 pm
BOB
- EWR
2 stops42h 13m
Multiple Airlines
Deal found 4/12![Multiple Airlines logo]()
$2,139
This Mytrip deal was found by Cheapflights users on 4/12. 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 6/1011:41 am
EWR
- BOB
3 stops35h 29m
Multiple Airlines
Sun 6/146:20 pm
BOB
- EWR
3 stops34h 20m
Multiple Airlines
Deal found 4/12![Multiple Airlines logo]()
$2,139
This Expedia deal was found by Cheapflights users on 4/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/317:26 pm
EWR
- BOB
2 stops42h 29m
Multiple Airlines
Sun 6/75:05 pm
BOB
- EWR
2 stops40h 28m
Multiple Airlines
Deal found 4/16![Multiple Airlines logo]()
$2,222
This Expedia deal was found by Cheapflights users on 4/14. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/147:26 pm
EWR
- BOB
2 stops42h 39m
Multiple Airlines
Wed 5/206:20 pm
BOB
- EWR
2 stops39h 13m
Multiple Airlines
Deal found 4/14![Multiple Airlines logo]()
$2,241
This KAYAK deal was found by Cheapflights users on 4/14. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/57:29 pm
EWR
- BOB
2 stops44h 01m
Multiple Airlines
Tue 5/126:50 pm
BOB
- EWR
2 stops38h 43m
Multiple Airlines
Deal found 4/14![Multiple Airlines logo]()
$2,264
This Mytrip deal was found by Cheapflights users on 4/13. 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.
Thu 5/2811:59 am
LGA
- BOB
3 stops35h 56m
Multiple Airlines
Thu 6/46:50 pm
BOB
- LGA
3 stops34h 10m
Multiple Airlines
Deal found 4/13![Multiple Airlines logo]()
$2,428
This Mytrip deal was found by Cheapflights users on 4/14. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/3011:59 am
LGA
- BOB
3 stops26h 36m
Multiple Airlines
Sat 6/67:50 pm
BOB
- LGA
3 stops39h 10m
Multiple Airlines
Deal found 4/14![Multiple Airlines logo]()
$2,486
This Mytrip deal was found by Cheapflights users on 4/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/1711:59 am
LGA
- BOB
3 stops25h 56m
Multiple Airlines
Sun 5/246:25 pm
BOB
- LGA
3 stops34h 35m
Multiple Airlines
Deal found 4/17![Multiple Airlines logo]()
$2,554
This Mytrip deal was found by Cheapflights users on 4/14. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/110:59 am
LGA
- BOB
3 stops27h 06m
Multiple Airlines
Sun 5/107:40 pm
BOB
- LGA
3 stops33h 20m
Multiple Airlines
Deal found 4/14![Multiple Airlines logo]()
$2,635
This Mytrip deal was found by Cheapflights users on 4/14. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/2810:30 am
LGA
- BOB
3 stops35h 35m
Multiple Airlines
Fri 6/56:40 pm
BOB
- LGA
3 stops34h 20m
Multiple Airlines
Deal found 4/14![Multiple Airlines logo]()
$3,318
Last-minute flights to Leeward IslandsDiscover last-minute flight deals to Leeward Islands. Data last updated April 17, 2026 and is based on user searches.
Discover last-minute flight deals to Leeward Islands. Data last updated April 17, 2026 and is based on user searches.
This FlightHub deal was found by Cheapflights users on 4/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/174:26 pm
JFK
- BOB
2 stops23h 49m
Multiple Airlines
Fri 4/246:40 pm
BOB
- JFK
2 stops31h 19m
Multiple Airlines
Deal found 4/16![Multiple Airlines logo]()
$1,715
This Trip.com deal was found by Cheapflights users on 4/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/238:11 pm
JFK
- BOB
2 stops49h 09m
Multiple Airlines
Sun 4/267:40 pm
BOB
- JFK
2 stops30h 19m
Multiple Airlines
Deal found 4/16![Multiple Airlines logo]()
$1,531
This FlightHub deal was found by Cheapflights users on 4/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/237:15 am
JFK
- BOB
2 stops30h 35m
Multiple Airlines
Mon 4/2712:30 pm
BOB
- JFK
2 stops27h 23m
Multiple Airlines
Deal found 4/17![Multiple Airlines logo]()
$1,816
This Justfly.com deal was found by Cheapflights users on 4/12. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/267:59 am
EWR
- BOB
2 stops30h 51m
Multiple Airlines
Sun 5/37:40 pm
BOB
- EWR
2 stops28h 23m
Multiple Airlines
Deal found 4/12![Multiple Airlines logo]()
$1,211
This FlightHub deal was found by Cheapflights users on 4/14. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/297:59 am
EWR
- BOB
2 stops30h 11m
Multiple Airlines
Wed 5/66:20 pm
BOB
- EWR
2 stops29h 43m
Multiple Airlines
Deal found 4/14![Multiple Airlines logo]()
$1,283
This FlightHub deal was found by Cheapflights users on 4/14. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/17:59 am
EWR
- BOB
2 stops32h 16m
Multiple Airlines
Wed 5/67:35 pm
BOB
- EWR
2 stops28h 28m
Multiple Airlines
Deal found 4/14![Multiple Airlines logo]()
$1,328
This FlightHub deal was found by Cheapflights users on 4/13. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/67:59 am
EWR
- BOB
2 stops30h 21m
Multiple Airlines
Wed 5/137:10 pm
BOB
- EWR
2 stops37h 31m
Multiple Airlines
Deal found 4/13![Multiple Airlines logo]()
$1,336
This FlightHub deal was found by Cheapflights users on 4/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/65:28 pm
JFK
- BOB
2 stops22h 42m
Multiple Airlines
Wed 5/137:10 pm
BOB
- JFK
2 stops30h 27m
Multiple Airlines
Deal found 4/16![Multiple Airlines logo]()
$1,417
This lastminute.com deal was found by Cheapflights users on 4/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure lastminute.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/84:30 pm
JFK
- BOB
2 stops22h 05m
Multiple Airlines
Fri 5/297:20 pm
BOB
- JFK
2 stops21h 39m
Multiple Airlines
Deal found 4/17![Multiple Airlines logo]()
$1,686
This FlightHub deal was found by Cheapflights users on 4/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/107:59 am
EWR
- BOB
2 stops29h 56m
Multiple Airlines
Sun 5/176:55 pm
BOB
- EWR
2 stops29h 15m
Multiple Airlines
Deal found 4/16![Multiple Airlines logo]()
$1,454
This FlightHub deal was found by Cheapflights users on 4/15. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/154:05 pm
JFK
- BOB
2 stops22h 00m
Multiple Airlines
Fri 5/226:40 pm
BOB
- JFK
2 stops30h 57m
Multiple Airlines
Deal found 4/15![Multiple Airlines logo]()
$1,720
This Trip.com deal was found by Cheapflights users on 4/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/175:58 pm
EWR
- BOB
2 stops23h 27m
Multiple Airlines
Sun 5/246:20 pm
BOB
- EWR
2 stops29h 50m
Multiple Airlines
Deal found 4/17![Multiple Airlines logo]()
$1,755
One-way flights to Leeward IslandsSearch for one-way flight options to Leeward Islands. Find affordable one-way fares based on user searches. Data last updated April 17, 2026.
Search for one-way flight options to Leeward Islands. Find affordable one-way fares based on user searches. Data last updated April 17, 2026.
This FlightHub deal was found by Cheapflights users on 4/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/85:28 pm
JFK
- BOB
2 stops19h 37m
Multiple Airlines
Deal found 4/16![Multiple Airlines logo]()
$685
This FlightHub deal was found by Cheapflights users on 4/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/87:59 am
EWR
- BOB
2 stops32h 16m
Multiple Airlines
Deal found 4/16![Multiple Airlines logo]()
$685
Find flight deals to Leeward Islands
Find the latest flights to Leeward Islands in 2026, with up-to-date prices and availability. In the last 7 days, Cheapflights users made a total of 2,558,603 searches and data was last updated on April 17, 2026.
Round-trip from | $1,211 |
|---|---|
One-way from | $685 |
Cheapflights Fare Finder
Locate flights to Leeward Islands that fit your budget, with regularly updated fares and availability. In the last 7 days, Cheapflights users made a total of 2,558,603 searches and data was last updated on April 17, 2026.
Use the filters below to find and compare flights to Leeward Islands that are best for you.
Fly from
Route
Depart
Return
Cheapest round-trip
NewarkVaitape
EWR - BOB
EWRBOB
Newark
Wed 5/6
7:59 am-8:20 am
2 stops30h 21m
Vaitape Motu-Mute
Wed 5/13
7:10 pm-2:41 pm
2 stops37h 31m
$1,336
New YorkVaitape
JFK - BOB
JFKBOB
New York John F Kennedy Intl
Wed 5/6
5:28 pm-10:10 am
2 stops22h 42m
Vaitape Motu-Mute
Wed 5/13
7:10 pm-7:37 am
2 stops30h 27m
$1,417
New YorkVaitape
JFK - BOB
JFKBOB
New York John F Kennedy Intl
Wed 6/10
9:30 am-8:05 am
2 stops28h 35m
Vaitape Motu-Mute
Sun 6/14
6:20 pm-6:20 am
2 stops30h 00m
$1,457
New YorkVaitape
JFK - BOB
JFKBOB
New York John F Kennedy Intl
Wed 7/8
9:30 am-8:05 am
2 stops28h 35m
Vaitape Motu-Mute
Sun 7/12
6:25 pm-6:20 am
2 stops29h 55m
$1,631
Quickest round-trip
New YorkVaitape
JFK - BOB
JFKBOB
New York John F Kennedy Intl
Fri 5/8
4:30 pm-8:35 am
2 stops22h 05m
Vaitape Motu-Mute
Fri 5/29
7:20 pm-10:59 pm
2 stops21h 39m
$1,686
New YorkVaitape
JFK - BOB
JFKBOB
New York John F Kennedy Intl
Wed 6/17
11:30 am-8:20 am
2 stops26h 50m
Vaitape Motu-Mute
Sun 7/5
7:40 pm-6:20 am
2 stops28h 40m
$1,708
New YorkVaitape
JFK - BOB
JFKBOB
New York John F Kennedy Intl
Sun 7/5
9:30 am-8:20 am
2 stops28h 50m
Vaitape Motu-Mute
Sun 7/12
6:25 pm-6:20 am
2 stops29h 55m
$1,711
New YorkVaitape
JFK - BOB
JFKBOB
New York John F Kennedy Intl
Fri 5/15
4:05 pm-8:05 am
2 stops22h 00m
Vaitape Motu-Mute
Fri 5/22
6:40 pm-7:37 am
2 stops30h 57m
$1,720
New YorkVaitape
JFK - BOB
JFKBOB
New York John F Kennedy Intl
Fri 5/15
4:30 pm-8:35 am
2 stops22h 05m
Vaitape Motu-Mute
Mon 5/18
7:35 pm-11:59 pm
2 stops22h 24m
$1,898
New YorkVaitape
JFK - BOB
JFKBOB
New York John F Kennedy Intl
Thu 5/7
11:00 am-9:55 am
2 stops28h 55m
Vaitape Motu-Mute
Thu 5/21
2:20 pm-9:16 pm
2 stops24h 56m
$1,898
Showing 1-10 of 26 resultsSorted by cheapest first
Best time to book a flight to Leeward Islands
Have a flexible travel schedule? Discover the best time to fly to Leeward Islands with our price prediction graph.
EWR-BOB
JFK-BOB
LGA-BOB
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 to Leeward Islands
NYC-PFLI
EWR-BOB
JFK-BOB
LGA-BOB
How long is the flight to Leeward Islands?
On average, a flight from New York to Leeward Islands takes 28 hours 38 minutes. Flights to Leeward Islands from other popular cities in USA will vary in length. Below are a few examples of popular routes and their flight times.
Rainfall in Leeward Islands by month
Plan your trip to Leeward Islands by taking into account the average rainfall totals by month.
In terms of precipitation, rainfall in Leeward Islands ranges from 2.8 - 10.2 inches per month. December is typically the wettest month, when rainfall can reach 10.2 in. August is typically the driest time to visit Leeward Islands when rainfall is around 2.8 in.
Temperature in Leeward Islands by month
Plan your trip to Leeward Islands by taking into account the average temperature totals by month.
If weather is an important factor for your trip to Leeward Islands, use this chart to help with planning. For those seeking warmer temperatures, January is the ideal time of year to visit, when temperatures reach an average of 78.8 F. Travelers looking to avoid the cold should look outside of July, when temperatures are typically at their lowest (around 75.2 F).
What are the most popular places to fly to in Leeward Islands?
Destination popularity is based on the amount of flight searches to Leeward Islands in the last few years. This data was updated on April 17, 2026.
The most popular places in Leeward Islands to fly to are Vaitape and Raiatea.
FAQs about flying to Leeward Islands
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