In 1908, Cliff Dwellers entered into a lease for the eighth floor and the ninth-story penthouse above Orchestra Hall (now Symphony Center) at 220 South Michigan Avenue.

[4] The club's interior, and the meeting space called the "kiva", was designed by Chicago architect Howard Van Doren Shaw, and featured the mural Navaho by John Warner Norton.

In 1996, the Cliff Dwellers moved their meeting place from the penthouse above Orchestra Hall (now Symphony Center) to the 22nd floor of the Borg-Warner building.

Authors Stuart Dybek and Scott Turow, Chicago sculptors Terrence Karpowicz and Richard Hunt, Chicago historian Tim Samuelson, investor and philanthropist Richard Driehaus, photographer and journalist Lee Bey, and architect Carter Manny are recent honorary members of the Club.

In addition, the Club hosts numerous events every month, showcasing musicians, dancers, and actors in unique and exciting performances.

Throughout the year, the Foundation provides grants to arts-oriented organizations and individuals, presents performances at the Club, and sponsors an annual music competition.