A beach with white sand and turquoise water. There are several sailboats on the shore.

Cheap Flights to Anguilla from $298

View $298 flight on Mon, Jan 25, 2027Opens in a new window

Popular airlines to Anguilla

  • American Airlines

  • United

  • Hahn Air Systems

  • Cape Air

  • FlexFlight

  • Tradewind Aviation

  • Be in the know

    Get alerts if flight prices drop or rise*

  • Book smarter

    Save up to 30% on select hotels after you book a flight*

  • Earn twice

    Earn your airline miles on top of our OneKeyCash
    Learn about One Key

How much is the cheapest flight to Anguilla?

Prices were available within the past 7 days and start at $298 for one-way flights and $633 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

American Airlines
American Airlines
American Airlines
American Airlines
BermudAir
BermudAir
American Airlines
JetBlue Airways
Cape Air
Tradewind Aviation

Trending flights to Anguilla

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

American Airlines

Book with confidence

Enjoy extra legroom, flight flexibility, and a seamless travel experience.

Travel information

*Flight schedules are subject to change.

*Available to One Key members.

*Flight schedules are subject to change.

*Available to One Key members.

Explore a world of travel with Expedia