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Vacations from Winnipeg

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

Santiago de Cuba, Cuba
Save up to 49%!
Toronto to Santiago de Cuba
Wed, January 22, 2020 7 days All inclusive
Reg. $1,155
From $585 taxes and fees incl.
Prefer another date?
Varadero, Cuba
Save up to 46%!
Toronto to Varadero
Mon, February 3, 2020 7 days All inclusive
Reg. $1,165
From $625 taxes and fees incl.
Prefer another date?
Save up to 47%!
Toronto to Varadero
Mon, February 3, 2020 7 days All inclusive
Reg. $1,185
From $625 taxes and fees incl.
Prefer another date?
Havana, Cuba
Save up to 24%!
Toronto to Havana
Mon, February 3, 2020 7 days All inclusive
Reg. $915
From $695 taxes and fees incl.
Prefer another date?
Holguin, Cuba
Save up to 31%!
Toronto to Holguin
Wed, January 29, 2020 7 days All inclusive
Reg. $1,045
From $725 taxes and fees incl.
Prefer another date?
Varadero, Cuba
Save up to 38%!
Toronto to Varadero
Tue, March 3, 2020 7 days All inclusive
Reg. $1,185
From $735 taxes and fees incl.
Prefer another date?
Santiago de Cuba, Cuba
Save up to 45%!
Toronto to Santiago de Cuba
Wed, January 22, 2020 7 days All inclusive
Reg. $1,335
From $735 taxes and fees incl.
Prefer another date?
Varadero, Cuba
Save up to 24%!
Toronto to Varadero
Mon, February 3, 2020 7 days All inclusive
Reg. $985
From $745 taxes and fees incl.
Prefer another date?
Santiago de Cuba, Cuba
Save up to 40%!
Toronto to Santiago de Cuba
Wed, January 22, 2020 7 days All inclusive
Reg. $1,255
From $755 taxes and fees incl.
Prefer another date?
Cayo Largo, Cuba
Save up to 50%!
Toronto to Cayo Largo
Fri, January 31, 2020 7 days All inclusive
Reg. $1,515
From $765 taxes and fees incl.
Prefer another date?
Cayo Largo, Cuba
Save up to 46%!
Toronto to Cayo Largo
Fri, January 31, 2020 7 days All inclusive
Reg. $1,405
From $765 taxes and fees incl.
Prefer another date?
Save up to 34%!
Toronto to Holguin
Wed, January 29, 2020 7 days All inclusive
Reg. $1,175
From $775 taxes and fees incl.
Prefer another date?
Holguin, Cuba
Save up to 32%!
Toronto to Holguin
Wed, January 29, 2020 7 days All inclusive
Reg. $1,155
From $785 taxes and fees incl.
Prefer another date?
Havana, Cuba
Save up to 22%!
Toronto to Havana
Tue, March 3, 2020 7 days All inclusive
Reg. $1,015
From $795 taxes and fees incl.
Prefer another date?
Cayo Santa Maria, Cuba
Save up to 42%!
Toronto to Cayo Santa Maria
Thu, January 30, 2020 7 days All inclusive
Reg. $1,375
From $795 taxes and fees incl.
Prefer another date?
Manzanillo de Cuba, Cuba
Save up to 41%!
Toronto to Manzanillo de Cuba
Wed, March 4, 2020 7 days All inclusive
Reg. $1,355
From $795 taxes and fees incl.
Prefer another date?
Save up to 39%!
Toronto to Varadero
Tue, March 3, 2020 7 days All inclusive
Reg. $1,315
From $805 taxes and fees incl.
Prefer another date?
Varadero, Cuba
Save up to 35%!
Toronto to Varadero
Tue, March 3, 2020 7 days All inclusive
Reg. $1,255
From $815 taxes and fees incl.
Prefer another date?
Cayo Santa Maria, Cuba
Save up to 43%!
Toronto to Cayo Santa Maria
Thu, January 30, 2020 7 days All inclusive
Reg. $1,435
From $815 taxes and fees incl.
Prefer another date?
Cayo Coco, Cuba
Save up to 37%!
Toronto to Cayo Coco
Tue, February 4, 2020 7 days All inclusive
Reg. $1,295
From $815 taxes and fees incl.
Prefer another date?
Save up to 39%!
Toronto to Varadero
Mon, February 3, 2020 7 days All inclusive
Reg. $1,375
From $845 taxes and fees incl.
Prefer another date?
Varadero, Cuba
Save up to 39%!
Toronto to Varadero
Mon, February 3, 2020 7 days All inclusive
Reg. $1,385
From $845 taxes and fees incl.
Prefer another date?
Santiago de Cuba, Cuba
Save up to 33%!
Toronto to Santiago de Cuba
Wed, January 22, 2020 7 days All inclusive
Reg. $1,255
From $845 taxes and fees incl.
Prefer another date?
Save up to 42%!
Toronto to Varadero
Mon, February 3, 2020 7 days All inclusive
Reg. $1,465
From $855 taxes and fees incl.
Prefer another date?
Varadero, Cuba
Save up to 36%!
Toronto to Varadero
Mon, February 3, 2020 7 days All inclusive
Reg. $1,335
From $855 taxes and fees incl.
Prefer another date?
Varadero, Cuba
Save up to 39%!
Toronto to Varadero
Mon, February 3, 2020 7 days All inclusive
Reg. $1,395
From $855 taxes and fees incl.
Prefer another date?
Save up to 41%!
Toronto to Varadero
Mon, February 3, 2020 7 days All inclusive
Reg. $1,495
From $875 taxes and fees incl.
Prefer another date?
Cayo Santa Maria, Cuba
Save up to 44%!
Toronto to Cayo Santa Maria
Mon, February 3, 2020 7 days All inclusive
Reg. $1,555
From $875 taxes and fees incl.
Prefer another date?
Cayo Santa Maria, Cuba
Save up to 41%!
Toronto to Cayo Santa Maria
Thu, January 30, 2020 7 days All inclusive
Reg. $1,475
From $875 taxes and fees incl.
Prefer another date?
Cayo Largo, Cuba
Save up to 44%!
Toronto to Cayo Largo
Fri, January 31, 2020 7 days All inclusive
Reg. $1,565
From $875 taxes and fees incl.
Prefer another date?

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