$818+ 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 5/19. Fares are subject to change and may not be available on all flights or dates of travel.
— BOB
May 23 — May 301
Round-trip
1 adult, Economy
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Best
Last-minute
One-way
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 23, 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 23, 2026.
This FlightHub deal was found by Cheapflights users on 4/19. 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 26m
Multiple Airlines
Sun 5/176:55 pm
BOB
- EWR
2 stops29h 15m
Multiple Airlines
Deal found 4/19![Multiple Airlines logo]()
$1,413
This FlightHub deal was found by Cheapflights users on 4/20. 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 5/205:58 pm
EWR
- BOB
2 stops22h 27m
Multiple Airlines
Wed 5/276:20 pm
BOB
- EWR
2 stops29h 50m
Multiple Airlines
Deal found 4/20![Multiple Airlines logo]()
$1,522
This Justfly.com deal was found by Cheapflights users on 4/22. 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.
Fri 6/129:30 am
JFK
- BOB
2 stops27h 55m
Multiple Airlines
Wed 6/247:10 pm
BOB
- JFK
2 stops29h 10m
Multiple Airlines
Deal found 4/22![Multiple Airlines logo]()
$1,653
This FlightHub deal was found by Cheapflights users on 4/21. 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.
Sat 4/253:30 pm
JFK
- BOB
2 stops23h 05m
Multiple Airlines
Mon 4/277:35 pm
BOB
- JFK
2 stops19h 25m
Multiple Airlines
Deal found 4/21![Multiple Airlines logo]()
$1,734
This FlightHub deal was found by Cheapflights users on 4/19. 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.
Mon 7/611:30 am
JFK
- BOB
2 stops26h 45m
Multiple Airlines
Wed 7/227:00 pm
BOB
- JFK
2 stops29h 20m
Multiple Airlines
Deal found 4/19![Multiple Airlines logo]()
$1,745
This Priceline deal was found by Cheapflights users on 4/22. 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.
Wed 5/67:15 am
JFK
- BOB
2 stops32h 15m
Multiple Airlines
Sat 5/91:50 pm
BOB
- JFK
2 stops34h 10m
Multiple Airlines
Deal found 4/22![Multiple Airlines logo]()
$1,776
This FlightHub deal was found by Cheapflights users on 4/22. 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 11/85:29 pm
JFK
- BOB
2 stops21h 26m
Multiple Airlines
Sat 11/1412:55 pm
BOB
- JFK
2 stops27h 03m
Multiple Airlines
Deal found 4/22![Multiple Airlines logo]()
$1,816
This Orbitz deal was found by Cheapflights users on 4/18. 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.
Thu 11/267:59 pm
EWR
- BOB
2 stops41h 36m
Multiple Airlines
Wed 12/25:20 pm
BOB
- EWR
2 stops32h 15m
Multiple Airlines
Deal found 4/18![Multiple Airlines logo]()
$1,826
This Justfly.com deal was found by Cheapflights users on 4/22. 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.
Wed 8/2611:30 am
JFK
- BOB
2 stops28h 40m
Multiple Airlines
Sun 8/306:25 pm
BOB
- JFK
2 stops30h 54m
Multiple Airlines
Deal found 4/22![Multiple Airlines logo]()
$1,832
This FlightHub deal was found by Cheapflights users on 4/21. 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 9/114:46 pm
JFK
- BOB
2 stops20h 19m
Multiple Airlines
Wed 9/307:35 pm
BOB
- JFK
2 stops29h 44m
Multiple Airlines
Deal found 4/21![Multiple Airlines logo]()
$1,860
This FlightHub deal was found by Cheapflights users on 4/18. 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 7/129:30 am
JFK
- BOB
2 stops27h 55m
Multiple Airlines
Fri 7/174:25 pm
BOB
- JFK
2 stops31h 55m
Multiple Airlines
Deal found 4/18![Multiple Airlines logo]()
$1,922
This FlightHub deal was found by Cheapflights users on 4/18. 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 4/193:30 pm
JFK
- BOB
2 stops24h 25m
Multiple Airlines
Sun 4/265:05 pm
BOB
- JFK
2 stops21h 55m
Multiple Airlines
Deal found 4/18![Multiple Airlines logo]()
$1,960
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 23, 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 23, 2026.
This FlightHub deal was found by Cheapflights users on 4/22. 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 stops30h 11m
Multiple Airlines
Sun 5/176:55 pm
BOB
- EWR
2 stops29h 15m
Multiple Airlines
Deal found 4/22![Multiple Airlines logo]()
$1,454
This FlightHub deal was found by Cheapflights users on 4/20. 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 5/205:58 pm
EWR
- BOB
2 stops22h 27m
Multiple Airlines
Wed 5/276:20 pm
BOB
- EWR
2 stops29h 50m
Multiple Airlines
Deal found 4/20![Multiple Airlines logo]()
$1,522
This FlightHub deal was found by Cheapflights users on 4/18. 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 7/129:30 am
JFK
- BOB
2 stops27h 55m
Multiple Airlines
Fri 7/174:25 pm
BOB
- JFK
2 stops31h 55m
Multiple Airlines
Deal found 4/18![Multiple Airlines logo]()
$1,922
This Justfly.com deal was found by Cheapflights users on 4/20. 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 6/147:05 am
JFK
- BOB
2 stops33h 45m
Multiple Airlines
Mon 6/227:35 pm
BOB
- JFK
2 stops19h 58m
Multiple Airlines
Deal found 4/20![Multiple Airlines logo]()
$1,982
This FlightHub deal was found by Cheapflights users on 4/21. 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 7/2211:30 am
JFK
- BOB
2 stops26h 50m
Multiple Airlines
Wed 7/297:00 pm
BOB
- JFK
2 stops29h 20m
Multiple Airlines
Deal found 4/21![Multiple Airlines logo]()
$2,028
This Justfly.com deal was found by Cheapflights users on 4/22. 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.
Wed 6/34:05 pm
JFK
- BOB
2 stops22h 00m
Multiple Airlines
Fri 6/126:40 pm
BOB
- JFK
2 stops29h 40m
Multiple Airlines
Deal found 4/22![Multiple Airlines logo]()
$2,044
This KAYAK deal was found by Cheapflights users on 4/19. 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.
Mon 8/246:00 am
JFK
- RFP
2 stops41h 00m
Multiple Airlines
Mon 8/3110:55 am
RFP
- JFK
2 stops28h 51m
Multiple Airlines
Deal found 4/19![Multiple Airlines logo]()
$2,046
This FlightHub deal was found by Cheapflights users on 4/21. 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.
Sat 5/1611:00 am
JFK
- BOB
2 stops27h 35m
Multiple Airlines
Sat 5/235:50 pm
BOB
- JFK
2 stops23h 09m
Multiple Airlines
Deal found 4/21![Multiple Airlines logo]()
$2,057
This FlightHub deal was found by Cheapflights users on 4/19. 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.
Mon 5/186:15 am
JFK
- BOB
2 stops31h 40m
Multiple Airlines
Mon 5/257:35 pm
BOB
- JFK
2 stops37h 00m
Multiple Airlines
Deal found 4/19![Multiple Airlines logo]()
$2,068
This Mytrip deal was found by Cheapflights users on 4/21. 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 6/511:37 am
EWR
- BOB
3 stops26h 58m
Multiple Airlines
Fri 6/127:20 pm
BOB
- EWR
3 stops33h 20m
Multiple Airlines
Deal found 4/21![Multiple Airlines logo]()
$2,091
This Expedia deal was found by Cheapflights users on 4/18. 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.
Sat 5/27:29 pm
EWR
- BOB
2 stops41h 56m
Multiple Airlines
Sun 5/107:55 pm
BOB
- EWR
2 stops37h 36m
Multiple Airlines
Deal found 4/18![Multiple Airlines logo]()
$2,173
This Priceline deal was found by Cheapflights users on 4/22. 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 5/216:00 am
JFK
- BOB
2 stops31h 50m
Multiple Airlines
Mon 5/2512:30 pm
BOB
- JFK
2 stops28h 29m
Multiple Airlines
Deal found 4/22![Multiple Airlines logo]()
$2,194
This Mytrip deal was found by Cheapflights users on 4/22. 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 6/1211:41 am
EWR
- BOB
3 stops26h 54m
Multiple Airlines
Wed 6/2411:00 am
BOB
- EWR
3 stops42h 32m
Multiple Airlines
Deal found 4/22![Multiple Airlines logo]()
$2,203
This KAYAK deal was found by Cheapflights users on 4/19. 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 7/74:44 pm
JFK
- BOB
2 stops32h 16m
Multiple Airlines
Mon 7/209:00 am
BOB
- JFK
2 stops30h 34m
Multiple Airlines
Deal found 4/19![Multiple Airlines logo]()
$2,231
This KAYAK deal was found by Cheapflights users on 4/19. 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.
Mon 8/246:17 pm
EWR
- RFP
2 stops52h 03m
Multiple Airlines
Mon 8/313:50 pm
RFP
- EWR
2 stops41h 45m
Multiple Airlines
Deal found 4/19![Multiple Airlines logo]()
$2,273
This Mytrip deal was found by Cheapflights users on 4/22. 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 6/611:41 am
EWR
- BOB
3 stops26h 54m
Multiple Airlines
Sat 6/135:50 pm
BOB
- EWR
3 stops34h 50m
Multiple Airlines
Deal found 4/22![Multiple Airlines logo]()
$2,286
This Expedia deal was found by Cheapflights users on 4/20. 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 6/46:00 am
JFK
- RFP
2 stops31h 10m
Multiple Airlines
Thu 6/117:25 am
RFP
- JFK
3 stops32h 08m
Multiple Airlines
Deal found 4/20![Multiple Airlines logo]()
$2,440
This Priceline deal was found by Cheapflights users on 4/20. 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 6/46:00 am
JFK
- BOB
2 stops31h 50m
Multiple Airlines
Thu 6/116:25 pm
BOB
- JFK
2 stops21h 08m
Multiple Airlines
Deal found 4/20![Multiple Airlines logo]()
$2,460
This KAYAK deal was found by Cheapflights users on 4/22. 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 5/217:26 pm
EWR
- BOB
2 stops43h 09m
Multiple Airlines
Mon 5/257:35 pm
BOB
- EWR
2 stops37h 58m
Multiple Airlines
Deal found 4/22![Multiple Airlines logo]()
$2,622
This KAYAK deal was found by Cheapflights users on 4/19. 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.
Mon 5/187:26 pm
EWR
- BOB
2 stops43h 04m
Multiple Airlines
Mon 5/257:35 pm
BOB
- EWR
2 stops37h 58m
Multiple Airlines
Deal found 4/19![Multiple Airlines logo]()
$2,622
This FlightHub deal was found by Cheapflights users on 4/19. 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.
Mon 8/244:46 pm
JFK
- MAU
2 stops22h 14m
Multiple Airlines
Mon 8/313:35 pm
MAU
- JFK
2 stops42h 51m
Multiple Airlines
Deal found 4/19![Multiple Airlines logo]()
$2,663
This Travelocity deal was found by Cheapflights users on 4/19. 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.
Wed 7/227:29 pm
EWR
- BOB
2 stops42h 31m
Multiple Airlines
Thu 7/301:00 pm
BOB
- EWR
2 stops46h 13m
Multiple Airlines
Deal found 4/19![Multiple Airlines logo]()
$3,207
This Orbitz deal was found by Cheapflights users on 4/19. 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.
Fri 5/227:26 pm
EWR
- BOB
2 stops53h 09m
Multiple Airlines
Tue 5/266:00 pm
BOB
- EWR
2 stops39h 33m
Multiple Airlines
Deal found 4/19![Multiple Airlines logo]()
$3,319
Last-minute flights to Leeward IslandsDiscover last-minute flight deals to Leeward Islands. Data last updated April 23, 2026 and is based on user searches.
Discover last-minute flight deals to Leeward Islands. Data last updated April 23, 2026 and is based on user searches.
This FlightHub deal was found by Cheapflights users on 4/21. 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.
Sat 4/253:30 pm
JFK
- BOB
2 stops23h 05m
Multiple Airlines
Mon 4/277:35 pm
BOB
- JFK
2 stops19h 25m
Multiple Airlines
Deal found 4/21![Multiple Airlines logo]()
$1,734
This Expedia deal was found by Cheapflights users on 4/18. 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.
Sat 5/27:29 pm
EWR
- BOB
2 stops41h 56m
Multiple Airlines
Sun 5/107:55 pm
BOB
- EWR
2 stops37h 36m
Multiple Airlines
Deal found 4/18![Multiple Airlines logo]()
$2,173
This Priceline deal was found by Cheapflights users on 4/22. 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.
Wed 5/67:15 am
JFK
- BOB
2 stops32h 15m
Multiple Airlines
Sat 5/91:50 pm
BOB
- JFK
2 stops34h 10m
Multiple Airlines
Deal found 4/22![Multiple Airlines logo]()
$1,776
This FlightHub deal was found by Cheapflights users on 4/19. 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 5/85:29 pm
JFK
- BOB
2 stops21h 06m
Multiple Airlines
Fri 5/157:20 pm
BOB
- JFK
2 stops22h 39m
Multiple Airlines
Deal found 4/19![Multiple Airlines logo]()
$2,018
This FlightHub deal was found by Cheapflights users on 4/19. 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 26m
Multiple Airlines
Sun 5/176:55 pm
BOB
- EWR
2 stops29h 15m
Multiple Airlines
Deal found 4/19![Multiple Airlines logo]()
$1,413
This FlightHub deal was found by Cheapflights users on 4/19. 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 5/104:30 pm
JFK
- BOB
2 stops21h 15m
Multiple Airlines
Sun 5/175:05 pm
BOB
- JFK
2 stops24h 54m
Multiple Airlines
Deal found 4/19![Multiple Airlines logo]()
$2,817
This FlightHub deal was found by Cheapflights users on 4/21. 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.
Sat 5/1611:00 am
JFK
- BOB
2 stops27h 35m
Multiple Airlines
Sat 5/235:50 pm
BOB
- JFK
2 stops23h 09m
Multiple Airlines
Deal found 4/21![Multiple Airlines logo]()
$2,057
This Priceline deal was found by Cheapflights users on 4/18. 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.
Mon 5/186:15 am
JFK
- BOB
2 stops42h 15m
Multiple Airlines
Mon 5/2512:30 pm
BOB
- JFK
2 stops45h 59m
Multiple Airlines
Deal found 4/18![Multiple Airlines logo]()
$2,040
This Travelocity deal was found by Cheapflights users on 4/18. 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.
Mon 5/187:26 pm
EWR
- BOB
2 stops42h 39m
Multiple Airlines
Mon 5/258:05 am
BOB
- EWR
2 stops49h 28m
Multiple Airlines
Deal found 4/18![Multiple Airlines logo]()
$2,122
This FlightHub deal was found by Cheapflights users on 4/20. 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 5/205:58 pm
EWR
- BOB
2 stops22h 27m
Multiple Airlines
Wed 5/276:20 pm
BOB
- EWR
2 stops29h 50m
Multiple Airlines
Deal found 4/20![Multiple Airlines logo]()
$1,522
This Priceline deal was found by Cheapflights users on 4/20. 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.
Wed 5/204:30 pm
JFK
- BOB
2 stops45h 20m
Multiple Airlines
Wed 5/273:20 pm
BOB
- JFK
2 stops25h 39m
Multiple Airlines
Deal found 4/20![Multiple Airlines logo]()
$2,466
This Priceline deal was found by Cheapflights users on 4/22. 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 5/216:00 am
JFK
- BOB
2 stops31h 50m
Multiple Airlines
Mon 5/2512:30 pm
BOB
- JFK
2 stops28h 29m
Multiple Airlines
Deal found 4/22![Multiple Airlines logo]()
$2,194
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 23, 2026.
Search for one-way flight options to Leeward Islands. Find affordable one-way fares based on user searches. Data last updated April 23, 2026.
This Kiwi.com deal was found by Cheapflights users on 4/19. 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.
Tue 5/1910:29 pm
EWR
- BOB
3 stops39h 36m
Multiple Airlines
Deal found 4/19![Multiple Airlines logo]()
$818
This Kiwi.com deal was found by Cheapflights users on 4/19. 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.
Tue 5/1910:00 pm
LGA
- BOB
3 stops42h 10m
Multiple Airlines
Deal found 4/19![Multiple Airlines logo]()
$833
Find flights to Leeward Islands
Browse one-way and round-trip flights deals to Leeward Islands on Cheapflights. Flight deals are based on user searches and were last updated on April 23, 2026
Explore Leeward Islands
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 23, 2026.
Round-trip from | $1,413 |
|---|---|
One-way from | $818 |
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 23, 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
Sun 5/10
7:59 am-8:10 am
2 stops30h 11m
Vaitape Motu-Mute
Sun 5/17
6:55 pm-6:10 am
2 stops29h 15m
$1,454
NewarkVaitape
EWR - BOB
EWRBOB
Newark
Wed 5/20
5:58 pm-10:25 am
2 stops22h 27m
Vaitape Motu-Mute
Wed 5/27
6:20 pm-6:10 am
2 stops29h 50m
$1,522
New YorkVaitape
JFK - BOB
JFKBOB
New York John F Kennedy Intl
Sun 7/12
9:30 am-7:25 am
2 stops27h 55m
Vaitape Motu-Mute
Fri 7/17
4:25 pm-6:20 am
2 stops31h 55m
$1,922
New YorkVaitape
JFK - BOB
JFKBOB
New York John F Kennedy Intl
Sun 6/14
7:05 am-10:50 am
2 stops33h 45m
Vaitape Motu-Mute
Mon 6/22
7:35 pm-9:33 pm
2 stops19h 58m
$1,982
New YorkVaitape
JFK - BOB
JFKBOB
New York John F Kennedy Intl
Wed 7/22
11:30 am-8:20 am
2 stops26h 50m
Vaitape Motu-Mute
Wed 7/29
7:00 pm-6:20 am
2 stops29h 20m
$2,028
New YorkVaitape
JFK - BOB
JFKBOB
New York John F Kennedy Intl
Wed 6/3
4:05 pm-8:05 am
2 stops22h 00m
Vaitape Motu-Mute
Fri 6/12
6:40 pm-6:20 am
2 stops29h 40m
$2,044
New YorkRaiatea
JFK - RFP
JFKRFP
New York John F Kennedy Intl
Mon 8/24
6:00 am-5:00 pm
2 stops41h 00m
Raiatea
Mon 8/31
10:55 am-9:46 pm
2 stops28h 51m
$2,046
Quickest round-trip
New YorkVaitape
JFK - BOB
JFKBOB
New York John F Kennedy Intl
Sat 5/16
11:00 am-8:35 am
2 stops27h 35m
Vaitape Motu-Mute
Sat 5/23
5:50 pm-10:59 pm
2 stops23h 09m
$2,057
New YorkVaitape
JFK - BOB
JFKBOB
New York John F Kennedy Intl
Mon 5/18
6:15 am-7:55 am
2 stops31h 40m
Vaitape Motu-Mute
Mon 5/25
7:35 pm-2:35 pm
2 stops37h 00m
$2,068
NewarkVaitape
EWR - BOB
EWRBOB
Newark
Fri 6/5
11:37 am-8:35 am
3 stops26h 58m
Vaitape Motu-Mute
Fri 6/12
7:20 pm-10:40 am
3 stops33h 20m
$2,091
Showing 1-10 of 25 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
JFK-RFP
EWR-RFP
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
JFK-RFP
How long is the flight to Leeward Islands?
On average, a flight from New York to Leeward Islands takes 31 hours 2 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 23, 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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