In the early 1970s, Willoughby Council developed the 'Chatswood Plan' which marked Chatswood as the centre of future community infrastructure and emphasised the council's ongoing commitment to retail development. It had hopes that it would ensure the town centre's continuing importance as a regional retail centre. David Jones submitted a proposal to build a shopping centre that would contain two department stores David Jones and Myer. on a site in Archer Street. In 1975 the site in Archer Street was given an 'Interim Development Order'. David Jones's rival Grace Bros had also proposed to build a shopping centre containing a supermarket and another department store adjacent to its existing store which opened in 1961 on Victoria Avenue. In 1978 the David Jones proposal was approved after disputes between Grace Bros and the State Government. Pre-development work on Chatswood Chase had begun in 1981 before Grace Bros dropped its final legal challenge. The works involved demolition of residential cottages and the church that stood on the site which was later reconstructed on an adjacent block of land. Sections of Neridah Street and Mills Lane were permanently closed and incorporated into the site and an open natural watercourse piped and diverted. The centre was completed in 14 months. Chatswood Chase officially opened on 23 March 1983 by and was the first large scale shopping centre after the opening of Wallace Way and Lemon Grove in the 1980s. The centre contained a Coles New World supermarket, Kmart, David Jones and it was the home to the only Myer store in NSW until the early 1990s then briefly became Grace Bros before closing altogether. This made Chatswood the only suburb in Sydney to have two Grace Bros. stores around this time. The space vacated by Grace Bros became a food court and speciality stores. In 2003, Chatswood Chase was purchased by Centro. In 2007, Vicinity Centres proceeded with a large and extensive redevelopment, growing the centre's gross lettable area by approximately 10,300 m2. Total cost was around $185 million. The Trust previously reported the acquisition of an adjoining office building at 19 Havilah Street in Chatswood and has since also secured an option to purchase the access lane to Chatswood Chase off Malvern Avenue to facilitate the proposed redevelopment. This involved relocating Coles supermarket into a larger retail area, undertaking a major extension to the lower ground retail space, the introduction of a new food court, the addition of approximately 130 new car parking spaces and an upgrade to the Victoria Avenue entrance. Work on the expansion concluded in 2010 and the centre was renamed to Chatswood Chase Sydney. Apple opened its second retail store in Australia on 9 August 2008. In August 2012, Harvey Norman closed its store due to poor sales and was replaced by JB Hi-Fi.
Future
In May 2019, an expansion to the shopping centre was announced. The $327 million expansion included two new levels of shops, a seven screen cinema and "sunken oasis" dining plaza, served by extended trading hours and with an on-site gym and wellness facility.