Fly Tradewind Aviation to Anguilla from San Juan, Puerto Rico

Scheduled flights from San Juan depart from the Luis Muñoz Marín International Airport in San Juan and will operate from December 14, 2023 through April 8, 2024. Flight schedules are designed for convenient connections with major airlines to and from the United States and beyond!

Flights on Tradewind Aviation from San Juan, Puerto Rico to Anguilla are offered Thursdays through Mondays.

Visit for real-time availability. Tradewind will be adding flights from Antigua to Anguilla soon.

The Perks You Get Flying Tradewind Aviation to Anguilla

All Tradewind guests connecting through San Juan can relax and enjoy complimentary WiFi, snacks, and refreshments in Tradewind’s private lounge. Or upgrade to Tradewind’s enhanced, VIP Experience.

How Much it Costs to Fly Tradewind Aviation to Anguilla

Tickets between Anguilla and San Juan start at $345 USD plus taxes and fees. Booking is available at, directly with Tradewind Aviation’s reservation team, in all major GDS systems (TJ), and with the airline’s interline partners.

Private Charter Flights to Anguilla via Tradewind Aviation

Private charter flights are also available at any time from Puerto Rico, Antigua, the USVI, and from the mainland United States. Choose from their industry leading fleet of Pilatus PC-12s and Citation CJ3 Jets.

Other Airlines Flying to Anguilla from Puerto Rico

Silver Airways is another carrier, but based on traveler posts and reviews may not always be reliable. We recommend researching before finalizing your route and carrier plans.

More Ways to Fly Direct to Anguilla

Book your stay at Villa Alegria Anguilla and consider flying on Tradewind Aviation. Or read about more ways to get to Anguilla.

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