Chicago gives lip service to preservation, but the instinct isn’t strong. Nowadays, it’s about pragmatism. The city usually won’t demolish a building if it’s still structurally sound, but if a bigger development comes along, oh well. Rehabs often make the most financial sense (Old Post Office, Thompson Center) so preservationists do get their victories.
The full list of demolitions would make an adamant preservationist jump off a cliff from despair, because most would have been iconic buildings in any other city — though several of the later replacements are notable works themselves.
Federal Building
Replaced by Mies Van Der Rohe Federal Center
Chicago Stock Exchange,
Replaced by 30 N LaSalle
Masonic Temple
Replaced by Block 37
Home Insurance Building
Replaced by Art Deco Field Building