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Vacations from Windsor

Enjoy convenient flights departing from Windsor to top destinations across the Caribbean, Mexico and Central America. For our neighbouring Americans, you'll be pleased to know you can pay for your vacation in Canadian dollars!

Save up to 53%!
Toronto to Jamaica
Sun, January 10, 2021 7 days All inclusive
Reg. $2,605
From $1,225 taxes and fees incl.
Prefer another date?
Jamaica
Save up to 33%!
Toronto to Jamaica
Sun, January 10, 2021 7 days All inclusive
Reg. $2,135
From $1,425 taxes and fees incl.
Prefer another date?
Jamaica
Save up to 35%!
Toronto to Jamaica
Sun, January 10, 2021 7 days All inclusive
Reg. $2,235
From $1,455 taxes and fees incl.
Prefer another date?
Jamaica
Save up to 37%!
Toronto to Jamaica
Sun, January 10, 2021 7 days All inclusive
Reg. $2,345
From $1,475 taxes and fees incl.
Prefer another date?
Save up to 49%!
Toronto to Jamaica
Sun, January 10, 2021 7 days All inclusive
Reg. $3,045
From $1,555 taxes and fees incl.
Prefer another date?
Antigua, Antigua and Barbuda
Save up to 41%!
Toronto to Antigua
Sat, February 20, 2021 7 days All inclusive
Reg. $3,645
From $2,165 taxes and fees incl.
Prefer another date?
Antigua, Antigua and Barbuda
Save up to 39%!
Toronto to Antigua
Sat, February 20, 2021 7 days All inclusive
Reg. $3,745
From $2,275 taxes and fees incl.
Prefer another date?
Antigua, Antigua and Barbuda
Save up to 36%!
Toronto to Antigua
Sat, February 20, 2021 7 days All inclusive
Reg. $3,675
From $2,335 taxes and fees incl.
Prefer another date?
Save up to 8%!
Toronto to St. Maarten
Thu, February 18, 2021 7 days All inclusive
Reg. $2,655
From $2,435 taxes and fees incl.
Prefer another date?