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Photo: Octavio Ruiz Cervera, CC BY-SA 2.0 via Wikimedia Commons
The Playground has a few things going for it: the perfect location for beginning or ending the night with a show, a BYOB liquor license, and a non-profit co-op structure that makes the performers here some of the most enthusiastic and committed you'll find. Quality will vary by ensemble.
The Playground Theater is a continuously operating non-profit theater in Chicago dedicated to Modern Theatrical Improvisation, a form of theater invented in the city. The Playground was founded in 1997 by a collective of Chicago improvisors. Originally located on Halsted Street, the theater now produces shows at different theatrical venues across Chicago. The Playground Theater was created to provide a Chicago venue where improvisors could have complete artistic control over the work they produced.
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The Chicago home of the nationally famed performance art Blue Man Group. Shows in the evenings, with matinees included on weekends. If you've seen them elsewhere, you're not likely to see anything new here.
Ernie Banks, Harry Caray, the 1908 champs, and the 2016 champs; yes, this is the home of the Chicago Cubs, the North Side's beloved baseball team. Among ballparks, only Fenway in Boston can match the old-time beauty of Wrigley and its famous ivy-covered walls. If you'd like to see Wrigley without attending a game, tours are occasionally offered ($25).
Chicago's foremost rock venue, although other genres like electronic and hip hop figure in the lineup as well. If a band is on the verge of stardom and they're on their way through Chicago, the Metro has a knack for booking them. Many shows are all ages, and are generally affordable. Tickets general admission (e.g. standing room only), so be prepared to stand, and press forward for your right to see a guitarist's nostrils. Smart Bar, next door, is owned by the Metro and features good DJs most nights of the week.
Overshadowed by the magnificent Graceland Cemetery across the street in Uptown, the smaller, slightly overgrown Wunders was established in 1859 and features some intriguing monuments, with more of a forgotten-by-time atmosphere than its more famous neighbor. A third cemetery, Jewish Graceland, is directly south.
Great big wonderful park with plenty of softball fields, football and soccer fields, basketball and tennis courts, trees, and a nice walking path. The leafy surroundings make it a great place for the annual pumpkin patch in the fall.