Bearskin Airlines is a Canadian regional airline that has been in operation since 1963. Founded in Sioux Lookout, Ontario, the airline has served communities across Canada's north for more than 50 years. With its fleet of over 40 aircraft, Bearskin Airlines provides scheduled and charter services to more than 25 destinations throughout Ontario, Manitoba, and Nunavut. The airline is the largest and oldest airline in the region, and its history is intertwined with the region's own history of growth and development.

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Bearskin Airlines was founded in 1963 by local businessmen Jim and Bill Deacon, who wanted to provide air service to the Sioux Lookout area. They purchased an 11-seat de Havilland Beaver floatplane and began offering scheduled services to a handful of destinations. Over the next decade, Bearskin Airlines slowly expanded its operations, adding larger aircraft to its fleet and increasing its route network.

In 1972, Bearskin Airlines purchased its first turbine-powered aircraft, a 19-seat de Havilland Twin Otter. This aircraft was instrumental in the airline's expansion, and it allowed Bearskin to serve larger communities and open up new destinations. In the same year, Bearskin also began offering charter services for the first time, expanding its reach even further.

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In the 1980s, Bearskin Airlines began to focus on expanding its regional services in Ontario and Manitoba. This included the launch of service to Thunder Bay in 1983, the opening of a new terminal at Sioux Lookout in 1989, and the introduction of the Dash-8 aircraft to the fleet in 1994. The Dash-8 allowed Bearskin to increase its passenger capacity and provide more comfortable air travel.

In 1997, Bearskin Airlines began to offer flights to Nunavut, becoming the first regional airline to provide service to the region. This was a major milestone for the airline and allowed them to expand their service area even further. Since then, Bearskin has been a major player in the development of the region, providing vital air services to remote communities.

Bearskin Airlines has grown and evolved over the years, but it has also seen its share of challenges. In 1999, the airline was the subject of a federal investigation into its safety practices. The investigation resulted in the airline being fined and its safety practices being improved. In 2004, the airline experienced a major setback when one of its aircraft crashed near Red Lake, Ontario, killing all eight passengers on board.

Despite these challenges, Bearskin Airlines has continued to develop and expand its operations. In recent years, the airline has added new destinations, increased its fleet size, and added more modern aircraft, such as the ATR 42 and ATR 72. Bearskin Airlines has become an integral part of northern Canada, providing essential air travel services to the region's most remote communities.