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Nightlife goes sky-high at this intimate club on the 33rd floor of the W. Chicago Lakeshore hotel. Locals and guests mingle among ’70s retro furnishings while soul and light house music provide the beat (though there’s no dancing) to a backdrop of stunning views.

This influential team (Holabird 1854–1923; Roche 1855–1927) developed early Chicago-style skyscrapers including the Marquette (see Marquette Building).

The “father of the skyscraper” (1832–1907) who designed the first all-metal-framed structure in 1885 (see 1885: First Skyscraper).

A casual dress code, good food, and cheap beer attract all types to this bar especially for burgers and hearty soup.

The centrally positioned bar, promotes an open, Cheers-type feel, with conversation flowing among patrons. TVs typically air college sports, while dart boards provide participatory entertainment.

In Road to Perdition (2002) Tom Hanks is Michael Sullivan, an Irish gangster living in 1930s Chicago. After his wife and young son are murdered, he flees town with his older son. In seeking a safe refuge, they enter a hotel, the exterior of which is the beautiful Wrigley Building. However, the interior scenes were actually filmed at The Hilton Chicago.

A baseball lover’s park, Wrigley is a small and intimate stadium that’s far less intimidating for children than many larger stadia. A ticket to anywhere in the grandstand allows you to walk around and get to the rooftop terrace with its great views: the outfield stands can get rowdy, but a neighboring family section bans the beer that fuels the “bleacher bums.”

Built in 1914, this is the USA’s oldest National League baseball park. Home team, the Chicago Cubs, haven’t won a World Series championship since 1908 (before the field even existed), but that doesn’t stop Northsiders from being behind them every step of the way. In season (March– September), spending an afternoon cheering on the “Cubbies” in this marvelous stadium, with its ivy-clad walls, is a quintessential Chicago experience.