That year, a former Skyservice employee named Mark Williams approached the CEO of Sunwing Travel Group, Colin Hunter, and asked if he wanted to start an airline.

[8] In November 2005, a Boeing 737-800 departing from Toronto to Santiago de Cuba was the airline's inaugural flight.

[12] In June, 2012, an unnamed individual and Transat A.T. submitted information to the Canadian Transportation Agency that was believed to challenge Sunwing's ability to operate an airline on the grounds of foreign ownership.

[17] As of 2023, Sunwings offers buy on board service,[18] after previously providing free meals on longer flights.

[25] As of Summer 2015, the airline operated service to Caribbean destinations from Atlanta, Baltimore, Charlotte, Cincinnati, Columbus, Houston, Lansing, Milwaukee, Nashville, New Orleans, Newark, Philadelphia, Pittsburgh, and Rockford.

This is reciprocated during the winter months with TUI and Smartwings lease out several aircraft to Canada to operate Sunwing routes.