In 2010, Air Canada leased the Bombardier Q400s and began sub-leasing them to SRA.^[6] The aircraft had been operated by Lynx Aviation of Denver.^[7] They were delivered to Sky Regional between November 2010 and the beginning of 2011. The aircraft are configured with 74 seats,^[8] similar to the Porter Airlines fleet.^[9] The planes are painted in Air Canada Express livery. Russell Payson was founder and chairman of the board of SRA.^[10]

In October 2012, SRA added flights between Montreal and Moncton, New Brunswick.^[11] Since the early stages of operation the airline has been active in introducing new technology to its operation. Sky Regional was the first airline in Canada to adopt the Electronic Flight Bag (EFB). Each pilot at the company is issued an Apple iPad which is the platform for the EFB allowing crews to not only have quick access to flight plans and manuals but eliminate paper charts and numerous large manuals which previously would have been present on the flight deck.

Air Canada started to transfer its 15 Embraer E175 planes to SRA in April 2013 and completed the transfer in September 2013.^[12] In the fall of 2015 SRA added an additional 5 E175 aircraft to its fleet. These aircraft were previously operated by Azul Brazilian Airlines.

SRA introduced a fleet of Embraer E175 jets in March 2013 to serve US destinations such as New York, Newark, Boston, Philadelphia, Chicago, and Dallas/Fort Worth.^[12]

Between October and December 2015 the fleet of 20 was expanded to 25 after obtaining 5 additional Embraer E175s previously operated by Azul Brazilian Airlines. These aircraft were put into service in April 2016 allowing the airline to add routes to more US destination such as Denver International Airport, and Hartsfield-Jackson Atlanta International Airport.

In early 2017, SRA's fleet of 5 Bombardier Q400s were transferred to fellow Air Canada Express carrier Jazz Aviation with the last flight arriving into Montreal from Moncton on February 23. SRA received 5 additional E175s in early 2017. The first of the aircraft came into service on May 16 with the last going into service on July 1. These new aircraft features an extra 3 seats in business class for a total of 12 seats. The rest of the fleet were reconfigured by the end of 2017 to a 76-seat configuration.

In 2018, Brent Card was promoted to Vice-president Flight Operations.

On March 1, 2021, Air Canada announced that the airline was going to consolidate all regional flying under the Jazz banner thereby ending the affiliation between Sky Regional and Air Canada. The aircraft flown by Sky Regional, the Embraer E175, will be transferred to Jazz.^[13] On March 30, 2021, Sky Regional operated its last flight from Newark, NJ to Toronto.