Skip Navigation

Vacations from Winnipeg

Enjoy convenient flights departing from Winnipeg to top destinations across the Caribbean, Mexico and Central America.

Varadero, Cuba
Save up to 31%!
Windsor to Varadero
Thu, April 9, 2020 7 days All inclusive
Reg. $1,295
From $895 taxes and fees incl.
Prefer another date?
Cayo Santa Maria, Cuba
Save up to 33%!
Windsor to Cayo Santa Maria
Tue, March 24, 2020 7 days All inclusive
Reg. $1,335
From $895 taxes and fees incl.
Prefer another date?
Save up to 32%!
Windsor to Varadero
Thu, April 9, 2020 7 days All inclusive
Reg. $1,345
From $915 taxes and fees incl.
Prefer another date?
Varadero, Cuba
Save up to 30%!
Windsor to Varadero
Thu, April 9, 2020 7 days All inclusive
Reg. $1,325
From $925 taxes and fees incl.
Prefer another date?
Varadero, Cuba
Save up to 16%!
Windsor to Varadero
Thu, April 9, 2020 7 days All inclusive
Reg. $1,115
From $935 taxes and fees incl.
Prefer another date?
Varadero, Cuba
Save up to 33%!
Windsor to Varadero
Thu, April 9, 2020 7 days All inclusive
Reg. $1,405
From $935 taxes and fees incl.
Prefer another date?
Save up to 32%!
Windsor to Varadero
Thu, April 9, 2020 7 days All inclusive
Reg. $1,425
From $975 taxes and fees incl.
Prefer another date?
Cayo Santa Maria, Cuba
Save up to 24%!
Windsor to Cayo Santa Maria
Tue, April 7, 2020 7 days All inclusive
Reg. $1,285
From $975 taxes and fees incl.
Prefer another date?
Cayo Santa Maria, Cuba
Save up to 39%!
Windsor to Cayo Santa Maria
Tue, April 7, 2020 7 days All inclusive
Reg. $1,605
From $975 taxes and fees incl.
Prefer another date?
Cayo Santa Maria, Cuba
Save up to 34%!
Windsor to Cayo Santa Maria
Tue, April 7, 2020 7 days All inclusive
Reg. $1,485
From $975 taxes and fees incl.
Prefer another date?
Cayo Santa Maria, Cuba
Save up to 35%!
Windsor to Cayo Santa Maria
Tue, March 24, 2020 7 days All inclusive
Reg. $1,505
From $985 taxes and fees incl.
Prefer another date?
Varadero, Cuba
Save up to 43%!
Windsor to Varadero
Thu, April 9, 2020 7 days All inclusive
Reg. $1,745
From $995 taxes and fees incl.
Prefer another date?
Cayo Santa Maria, Cuba
Save up to 29%!
Windsor to Cayo Santa Maria
Tue, April 7, 2020 7 days All inclusive
Reg. $1,405
From $995 taxes and fees incl.
Prefer another date?
Cayo Santa Maria, Cuba
Save up to 29%!
Windsor to Cayo Santa Maria
Tue, April 7, 2020 7 days All inclusive
Reg. $1,405
From $995 taxes and fees incl.
Prefer another date?
Cayo Santa Maria, Cuba
Save up to 35%!
Windsor to Cayo Santa Maria
Tue, April 7, 2020 7 days All inclusive
Reg. $1,525
From $995 taxes and fees incl.
Prefer another date?
Cayo Santa Maria, Cuba
Save up to 36%!
Windsor to Cayo Santa Maria
Tue, April 7, 2020 7 days All inclusive
Reg. $1,545
From $995 taxes and fees incl.
Prefer another date?
Cayo Santa Maria, Cuba
Save up to 31%!
Windsor to Cayo Santa Maria
Tue, April 7, 2020 7 days All inclusive
Reg. $1,465
From $1,005 taxes and fees incl.
Prefer another date?
Cayo Santa Maria, Cuba
Save up to 42%!
Windsor to Cayo Santa Maria
Tue, March 24, 2020 7 days All inclusive
Reg. $1,735
From $1,005 taxes and fees incl.
Prefer another date?
Save up to 23%!
Windsor to Cayo Santa Maria
Tue, April 7, 2020 7 days All inclusive
Reg. $1,315
From $1,015 taxes and fees incl.
Prefer another date?
Varadero, Cuba
Save up to 32%!
Windsor to Varadero
Thu, April 9, 2020 7 days All inclusive
Reg. $1,515
From $1,025 taxes and fees incl.
Prefer another date?
Save up to 30%!
Windsor to Varadero
Thu, April 9, 2020 7 days All inclusive
Reg. $1,465
From $1,025 taxes and fees incl.
Prefer another date?
Varadero, Cuba
Save up to 27%!
Windsor to Varadero
Thu, April 9, 2020 7 days All inclusive
Reg. $1,415
From $1,035 taxes and fees incl.
Prefer another date?
Cayo Santa Maria, Cuba
Save up to 38%!
Windsor to Cayo Santa Maria
Tue, March 24, 2020 7 days All inclusive
Reg. $1,665
From $1,035 taxes and fees incl.
Prefer another date?
Havana, Cuba
Save up to 17%!
Windsor to Havana
Thu, March 26, 2020 7 days All inclusive
Reg. $1,265
From $1,045 taxes and fees incl.
Prefer another date?
Cayo Santa Maria, Cuba
Save up to 11%!
Windsor to Cayo Santa Maria
Tue, April 7, 2020 7 days All inclusive
Reg. $1,175
From $1,045 taxes and fees incl.
Prefer another date?
Save up to 23%!
Windsor to Varadero
Thu, April 9, 2020 7 days All inclusive
Reg. $1,375
From $1,065 taxes and fees incl.
Prefer another date?
Havana, Cuba
Save up to 17%!
Windsor to Havana
Thu, April 9, 2020 7 days All inclusive
Reg. $1,315
From $1,095 taxes and fees incl.
Prefer another date?
Save up to 44%!
Windsor to Cayo Santa Maria
Tue, March 24, 2020 7 days All inclusive
Reg. $1,965
From $1,095 taxes and fees incl.
Prefer another date?
Cayo Santa Maria, Cuba
Save up to 32%!
Windsor to Cayo Santa Maria
Tue, April 7, 2020 7 days All inclusive
Reg. $1,615
From $1,095 taxes and fees incl.
Prefer another date?
Varadero, Cuba
Save up to 21%!
Windsor to Varadero
Thu, April 9, 2020 7 days All inclusive
Reg. $1,405
From $1,105 taxes and fees incl.
Prefer another date?

Back to
top