Top Choice Observatory in Gold Coast

360° Chicago

This is the new name for the John Hancock Center Observatory. In many ways the view here surpasses the one at Willis Tower. The 94th-floor lookout has informative displays and the TILT feature (floor-to-ceiling wind…
Top Choice Museum in Gold Coast

Museum of Contemporary Art

Consider it the Art Institute’s brash, rebellious sibling, with especially strong minimalist, surrealist and conceptual photography collections, and permanent works by René Magritte, Cindy Sherman and Andy Warhol. C…
Library in Gold Coast

Newberry Library

The Newberry's public galleries are for bibliophiles: those who swoon over original Thomas Paine pamphlets about the French Revolution, or get weak-kneed seeing Thomas Jefferson's copy of the History of the Expediti…
Gallery in Gold Coast

City Gallery

Set inside the historic Water Tower, the gallery showcases Chicago-themed works by local photographers and artists.
Park in Gold Coast

Washington Square

This plain-looking park across from the Newberry Library has quite a history. In the 1920s it was known as ‘Bughouse Square,’ where communists, socialists, anarchists and other -ists congregated and gave soapbox ora…
Landmark in Gold Coast

Water Tower

The 154ft-tall, turreted tower is a defining city icon: it was the sole downtown survivor of the 1871 Great Chicago Fire, thanks to its yellow limestone bricks, which withstood the flames. Today the tower houses the…
Notable Building in Gold Coast

Original Playboy Mansion

The sexual revolution started in the basement ‘grotto’ of this 1899 manor. Hugh Hefner bought the mansion in 1959 and hung a brass plate over the door warning ‘If You Don’t Swing, Don’t Ring.’ Heavy partying ensued.…
Museum in Gold Coast

Chicago Sports Museum

To understand Chicago's tortured sports psyche, check out the memorabilia-filled cases at this gallery beside Harry Caray's 7th Inning Stretch tavern. Shake your head in sadness at the last-out ball from the 1945 Wo…
Architecture in Gold Coast

Charnley-Persky House

While he was still working for Louis Sullivan, Frank Lloyd Wright (who was 19 at the time) designed the 11-room Charnley-Persky House, which sparked a new era in architectural design. Why? Because it did away with V…
Museum in Gold Coast

International Museum of Surgical Science

Amputation saws, iron lungs and other early tools of the trade are strewn throughout this creaky mansion. The ancient Roman vaginal speculum leaves a lasting impression, while the pointy-ended hemorrhoid surgery ins…