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Vacations from Winnipeg

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

Varadero, Cuba
Save up to 49%!
Toronto to Varadero
Mon, March 9, 2020 7 days All inclusive
Reg. $1,185
From $605 taxes and fees incl.
Prefer another date?
Save up to 48%!
Toronto to Varadero
Mon, March 9, 2020 7 days All inclusive
Reg. $1,205
From $625 taxes and fees incl.
Prefer another date?
Save up to 40%!
Toronto to Holguin
Tue, March 24, 2020 7 days All inclusive
Reg. $1,085
From $655 taxes and fees incl.
Prefer another date?
Holguin, Cuba
Save up to 36%!
Toronto to Holguin
Tue, March 24, 2020 7 days All inclusive
Reg. $1,065
From $685 taxes and fees incl.
Prefer another date?
Santiago de Cuba, Cuba
Save up to 43%!
Toronto to Santiago de Cuba
Wed, March 4, 2020 7 days All inclusive
Reg. $1,195
From $685 taxes and fees incl.
Prefer another date?
Varadero, Cuba
Save up to 45%!
Toronto to Varadero
Sun, March 29, 2020 7 days All inclusive
Reg. $1,255
From $695 taxes and fees incl.
Prefer another date?
Varadero, Cuba
Save up to 41%!
Toronto to Varadero
Tue, April 7, 2020 7 days All inclusive
Reg. $1,205
From $715 taxes and fees incl.
Prefer another date?
Varadero, Cuba
Save up to 36%!
Toronto to Varadero
Sun, April 5, 2020 7 days All inclusive
Reg. $1,125
From $725 taxes and fees incl.
Prefer another date?
Holguin, Cuba
Save up to 38%!
Toronto to Holguin
Tue, March 24, 2020 7 days All inclusive
Reg. $1,195
From $735 taxes and fees incl.
Prefer another date?
Save up to 49%!
Toronto to Varadero
Mon, March 9, 2020 7 days All inclusive
Reg. $1,435
From $735 taxes and fees incl.
Prefer another date?
Cayo Coco, Cuba
Save up to 45%!
Toronto to Cayo Coco
Tue, March 3, 2020 7 days All inclusive
Reg. $1,325
From $735 taxes and fees incl.
Prefer another date?
Santiago de Cuba, Cuba
Save up to 38%!
Toronto to Santiago de Cuba
Wed, March 11, 2020 7 days All inclusive
Reg. $1,195
From $745 taxes and fees incl.
Prefer another date?
Cayo Coco, Cuba
Save up to 46%!
Toronto to Cayo Coco
Tue, March 3, 2020 7 days All inclusive
Reg. $1,415
From $765 taxes and fees incl.
Prefer another date?
Cayo Largo, Cuba
Save up to 46%!
Toronto to Cayo Largo
Fri, March 27, 2020 7 days All inclusive
Reg. $1,415
From $765 taxes and fees incl.
Prefer another date?
Havana, Cuba
Save up to 22%!
Toronto to Havana
Mon, March 23, 2020 7 days All inclusive
Reg. $995
From $775 taxes and fees incl.
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Cayo Largo, Cuba
Save up to 48%!
Toronto to Cayo Largo
Fri, March 27, 2020 7 days All inclusive
Reg. $1,515
From $785 taxes and fees incl.
Prefer another date?
Varadero, Cuba
Save up to 43%!
Toronto to Varadero
Mon, March 9, 2020 7 days All inclusive
Reg. $1,405
From $795 taxes and fees incl.
Prefer another date?
Manzanillo de Cuba, Cuba
Save up to 48%!
Toronto to Manzanillo de Cuba
Wed, March 18, 2020 7 days All inclusive
Reg. $1,535
From $795 taxes and fees incl.
Prefer another date?
Santiago de Cuba, Cuba
Save up to 39%!
Toronto to Santiago de Cuba
Wed, March 4, 2020 7 days All inclusive
Reg. $1,305
From $795 taxes and fees incl.
Prefer another date?
Save up to 41%!
Toronto to Holguin
Tue, March 24, 2020 7 days All inclusive
Reg. $1,365
From $805 taxes and fees incl.
Prefer another date?
Havana, Cuba
Save up to 21%!
Toronto to Havana
Thu, March 5, 2020 7 days All inclusive
Reg. $1,025
From $805 taxes and fees incl.
Prefer another date?
Varadero, Cuba
Save up to 43%!
Toronto to Varadero
Mon, March 9, 2020 7 days All inclusive
Reg. $1,415
From $805 taxes and fees incl.
Prefer another date?
Save up to 42%!
Toronto to Varadero
Mon, March 9, 2020 7 days All inclusive
Reg. $1,395
From $805 taxes and fees incl.
Prefer another date?
Varadero, Cuba
Save up to 37%!
Toronto to Varadero
Mon, March 9, 2020 7 days All inclusive
Reg. $1,295
From $815 taxes and fees incl.
Prefer another date?
Varadero, Cuba
Save up to 43%!
Toronto to Varadero
Sun, April 5, 2020 7 days All inclusive
Reg. $1,425
From $815 taxes and fees incl.
Prefer another date?
Save up to 41%!
Toronto to Varadero
Sun, April 5, 2020 7 days All inclusive
Reg. $1,375
From $815 taxes and fees incl.
Prefer another date?
Save up to 38%!
Toronto to Holguin
Tue, March 31, 2020 7 days All inclusive
Reg. $1,315
From $815 taxes and fees incl.
Prefer another date?
Save up to 46%!
Toronto to Varadero
Mon, March 9, 2020 7 days All inclusive
Reg. $1,515
From $825 taxes and fees incl.
Prefer another date?
Varadero, Cuba
Save up to 52%!
Toronto to Varadero
Tue, March 24, 2020 7 days All inclusive
Reg. $1,775
From $845 taxes and fees incl.
Prefer another date?
Cayo Santa Maria, Cuba
Save up to 35%!
Toronto to Cayo Santa Maria
Mon, March 30, 2020 7 days All inclusive
Reg. $1,305
From $845 taxes and fees incl.
Prefer another date?

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