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Formed by Skyservice Business Aviation to operate Air Canada commuter flights from Toronto-City Airport. Began operations on May 1, 2011, under the Air Canada Express brand, initially flying Bombardier Q400s between Toronto City Airport and Montréal-Trudeau Airport.
Introduced Embraer E175 jets in 2013 to serve U.S. destinations such as New York, Boston, Chicago, and Dallas/Fort Worth. The fleet expanded to 25 aircraft by 2016, allowing the addition of routes to Denver and Atlanta. Transferred its Q400s to Jazz Aviation in 2017 and reconfigured E175 fleet to 76-seat configuration.
On March 1, 2021, Air Canada announced the consolidation of its regional operations under Jazz Aviation, ending its partnership with Sky Regional. Operated the final flight from Newark to Toronto on March 30, 2021.
