North Star Air began operations in 1997 with the purchase of two single-engine Beaver aircraft on floats based on Pickle Lake. In cooperation with its sister company Canoe Frontier, North Star Air flew paddlers and fishermen into Ontario's Last Frontier north of Pickle Lake. Shortly thereafter a DHC-3 Turbo-Otter and Cessna Caravan on floats joined the operation. In 2001, North Star Air moved from its water base on Pickle Lake to the Pickle Lake Airport. 

In 2005 North Star Air took over Canadadirect, a small airline flying American fisherman into Northern Ontario, in the process providing North Star Air its first PC-12 aircraft. A Cessna Grand Caravan was delivered a year later to address the growing demand for cargo movement out of Pickle Lake into the northern communities.

In 2012 Frank Kelner joined the North Star Air team, bringing with him over 40 years of aviation experience in the North including 20,000+ hours flying time and running numerous airlines including Kelner Airways (present-day Wasaya Airways). Identifying the need for another carrier in Northwest Ontario, the company then embarked on an ambitious expansion plan to improve reliability and competitiveness in the industry. This plan included the creation of a separate airline dedicated to cargo movement. Cargo North was born as the first operator in the world to use the Basler BT-67 for high-frequency, short-distance freight runs. 

In 2013 North Star Air/Cargo North partnered with Muskrat Dam and Sachigo Lake First Nations through a revenue-sharing agreement. In conjunction with these agreements, North Star Air launched its Flex Flight service from Sioux Lookout. That same year Cargo North added a second Basler BT-67 aircraft. 

In 2014 North Star Air relocated its Headquarters from Pickle Lake to Thunder Bay to facilitate their growth. Cat Lake, Deer Lake, Kashechewan, Neskantaga, and North Caribou Lake partnered with North Star Air through revenue sharing agreements. To address the growing requirements of its community partners, North Star Air further expanded its Flex Flight network to Thunder Bay. A base was also opened in Red Lake to better service new strategic partners, Deer Lake and Cat Lake communities. 

In 2015 Bearskin Lake, Poplar Hill and Webequie joined the North Star Air team. A third Basler BT-67 aircraft was added along with two additional Pilatus PC-12 aircraft. That same year North Star Air was awarded the delivery contract for six North West Company (Northern) stores. Since being awarded this contract, North Star Air has maintained a 95% or greater on-time performance. This was a 15% improvement over any previous Northern Store carrier. 

In 2016 North Star Air and Cargo North merged to create one airline capable of delivering both the passenger and cargo services required in the North.

In June 2017 North Star Air was acquired by The North West Company, a Canadian retailer with a rich history of serving Canada's remote North for over 100 years. With the financial backing of North West, North Star Air added the larger passenger aircraft Dash 8-100 to meet the growing demand of its partner communities. The acquisition also marked North Star Air's expansion into Manitoba, including the opening of a Thompson, MB base and introduces the ATR 72-500 cargo aircraft to the fleet.

In June 2019 Eabametoong First Nation partners with North Star Air through the airlines revenue sharing agreement. North Star Air also increases their fleet with another Pilatus PC-12 aircraft and adds a second Dash 8-100 later in the year. 

In June 2020 CEO Frank Kelner announces the appointment of Jeff Stout as President and Chief Operating Officer, while Mr. Kelner remains as Chairman/CEO. These changes reflect NSA’s recent rapid growth and the continued opportunities seen for further expansion. Collectively, Frank, Jeff and Vice-President Tom Meilleur will continue to comprise the core management team that, along with an experienced senior team, has built North Star Air into a leading Canadian airline serving remote communities across multiple provinces.

In June 2021 North Star Air purchases a fifth ATR 72-500, which undergoes six months of modifications, including Large Cargo Door, more than doubling the width of the current door.

Today North Star Air services over 54 remote Northern communities with its fleet of 18 aircraft and 300+ dedicated employees. Most importantly, North Star Air has, and continues to, make a difference in the North. It's revenue sharing program has generated over $8 million for its strategic partners while providing safe, affordable and reliable air transportation solutions. 

North Star Air is the recipient of the 2019 Thunder Bay Chamber of Commerce Large Business Excellence Award and the 2019 NOBA Company of the Year (51+) Award.