Cheap flights from Windward

View NZ$1,009 flight on Mon, 2 Nov 2026Opens in a new window

Popular airlines from Windward

  • KLM

  • Air Caraibes

  • Corsair

  • Windward Island Airways International

  • FlexFlight

  • Cape Air

  • Hahn Air Systems

  • Be in the know

    Get alerts if flight prices drop or rise*

  • Book smarter

    Save up to 35% on select hotels after you book a flight*

  • Earn twice

    Earn your airline miles on top of our rewards
    Sign in

Cheapest flights from Windward

These prices were available within the past 7 days. Prices quoted are per person, return, for the period specified. Prices and availability are subject to change. Additional terms apply.

Windward Island Airways International
Mon, 2 Nov - Wed, 4 Nov
SBH
Gustavia
SJU
San Juan
NZ$1,784 Return, found 3 days ago
NZ$1,784
Return
found 3 days ago
Select Windward Island Airways International flight, departing Mon, 2 Nov from Gustavia to San Juan, returning Wed, 4 Nov, priced at NZ$1,784 found 3 days ago
Tradewind Aviation
Mon, 2 Nov - Wed, 4 Nov
SBH
Gustavia
SJU
San Juan
NZ$1,818 Return, found 3 days ago
NZ$1,818
Return
found 3 days ago
Select Tradewind Aviation flight, departing Mon, 2 Nov from Gustavia to San Juan, returning Wed, 4 Nov, priced at NZ$1,818 found 3 days ago
Cape Air
Mon, 2 Nov - Wed, 4 Nov
SBH
Gustavia
SJU
San Juan
NZ$1,830 Return, found 3 days ago
NZ$1,830
Return
found 3 days ago
Select Cape Air flight, departing Mon, 2 Nov from Gustavia to San Juan, returning Wed, 4 Nov, priced at NZ$1,830 found 3 days ago
Cape Air
Mon, 2 Nov - Wed, 4 Nov
SBH
Gustavia
SJU
San Juan
NZ$1,836 Return, found 3 days ago
NZ$1,836
Return
found 3 days ago
Select Cape Air flight, departing Mon, 2 Nov from Gustavia to San Juan, returning Wed, 4 Nov, priced at NZ$1,836 found 3 days ago
Windward Island Airways International
Mon, 2 Nov - Wed, 4 Nov
SBH
Gustavia
SJU
San Juan
NZ$1,844 Return, found 3 days ago
NZ$1,844
Return
found 3 days ago
Select Windward Island Airways International flight, departing Mon, 2 Nov from Gustavia to San Juan, returning Wed, 4 Nov, priced at NZ$1,844 found 3 days ago
Cape Air
Mon, 2 Nov - Wed, 4 Nov
SBH
Gustavia
SJU
San Juan
NZ$1,853 Return, found 3 days ago
NZ$1,853
Return
found 3 days ago
Select Cape Air flight, departing Mon, 2 Nov from Gustavia to San Juan, returning Wed, 4 Nov, priced at NZ$1,853 found 3 days ago
Windward Island Airways International
Mon, 2 Nov - Wed, 4 Nov
SBH
Gustavia
SJU
San Juan
NZ$1,859 Return, found 3 days ago
NZ$1,859
Return
found 3 days ago
Select Windward Island Airways International flight, departing Mon, 2 Nov from Gustavia to San Juan, returning Wed, 4 Nov, priced at NZ$1,859 found 3 days ago
Cape Air
Mon, 2 Nov - Wed, 4 Nov
SBH
Gustavia
SJU
San Juan
NZ$1,870 Return, found 3 days ago
NZ$1,870
Return
found 3 days ago
Select Cape Air flight, departing Mon, 2 Nov from Gustavia to San Juan, returning Wed, 4 Nov, priced at NZ$1,870 found 3 days ago
Tradewind Aviation
Mon, 2 Nov - Wed, 4 Nov
SBH
Gustavia
SJU
San Juan
NZ$1,878 Return, found 3 days ago
NZ$1,878
Return
found 3 days ago
Select Tradewind Aviation flight, departing Mon, 2 Nov from Gustavia to San Juan, returning Wed, 4 Nov, priced at NZ$1,878 found 3 days ago
Cape Air
Mon, 2 Nov - Wed, 4 Nov
SBH
Gustavia
SJU
San Juan
NZ$1,879 Return, found 3 days ago
NZ$1,879
Return
found 3 days ago
Select Cape Air flight, departing Mon, 2 Nov from Gustavia to San Juan, returning Wed, 4 Nov, priced at NZ$1,879 found 3 days ago
*Available to Expedia members.