For Ottawa:
The Capital Theatre - A 2500 seat Art Deco movie theatre built downtown and demolished in the seventies. Replaced by same office building, though I'm not sure which.
Daly Building - Ottawa's first department store and only building in Ottawa built in the Chicago style. It was demolished in 1991 after the NCC's attempt to find a developer to restore it to safe conditions failed due to the expense of the venture. It was the first designated heritage building in Ottawa to be demolished and the site wasn't used until 700 Sussex, was built there.
An almost demolished, but luckily saved and rehabilitated is the Aberdeen Pavilion.