Expensive Chicago Penthouses for Sale Friday, March 18th, 2022 at 9:10am. Linda Shaughnessy 1500 N Lake Shore Dr penthouse $12,000,000 ~ Rosario Candela's exclusive Gold Coast co-op apartment. A grand 8,000 SF with a 5,000 SF terrace LEARN MORE 1209 N Astor St penthouse $2,995,000 - Full floor 4,100 square feet totally rebuilt and renovated one-of-a-kind PH co-op in Chicago's Gold Coast LEARN MORE One Bennett penthouse $15,170,000. Full floor 7,500 square feet with 12'6" ceilings and a 65-foot long terrace LEARN MORE David Adler penthouse at 1325 N Astor St. $6,999,000. Full floor 8,000 SF with 3 terraces LEARN MORE Read Full Post »