Two of Chicago's most bustling neighborhoods can be found next to each other on the Near North Side. Between Old Town and Goose Island you'll find several of the city's most influential comedy clubs, one of Chicago's best breweries, a well-appointed new multiplex and more esoteric attractions.
RECOMMENDED: Our complete guide to Old Town and Goose Island
Things to do in Old Town and Goose Island
Even if you know nothing about improv, chances are you've heard of Second City. This is the place that put both sketch and improvised comedy on the map while launching the careers of many distinguished comics including Bill Murray, Tina Fey, Chris Farley, John Belushi, Joan Rivers, Stephen Colbert and Steve Carell. The company has been at the corner of North and Wells since 1967, but recent expansions have Second City occupying almost the entire Pipers Alley complex, with performances in the Mainstage and e.t.c. theaters, UP Comedy Club and four smaller theaters for student shows, as well as a massive new facility for the Second City Training Center and Harold Ramis Film School; grab a drink before or after the show at the 1959 Kitchen & Bar.
A few blocks to the west of Second City, another improv instution luxuriates in the four-theater complex it moved into in 2014 after decades in the cramped confines of Wrigleyville. Founded by late improv leged Del Close and Charna Halpern, who still runs it today, iO consistently puts the art of improv first, most noticeably via the Harold, its signature long-form. The shows are generally cheap and the classes a must for budding improvisers. The venue's expansive lobby bar is an inviting place to hang out even if you're not seeing a show.
This Catholic parish dates back to 1852, when it was founded to serve the German immigrant community settling in what is now Old Town; the church’s current building was one of the first houses of worship to rebuild and reopen following the Great Chicago Fire of 1871. Church docents offer tours of the building and its beautiful religious artwork following Sunday mass.
This oddly-shaped shoebox located down a gangway behind a taco place serves as home to the bold, scrappy Old Town troupe known for intense, often dark, diamond-hard works by resident playwrights Brett Neveu and Craig Wright and others of similar sensibility. A Red Orchid’s most famous ensemble member, Michael Shannon, returns regularly to perform with his old pals.
The L.A.-based movie theater chain brings Chicago its revamped, hassle-free take on the moviegoing experience by doing away with lines, general seating (you choose your seats when you purchase), lengthy trailers and sticky floors. The theater offers classic concessions, a cafe and a bar with craft beer, wine and cocktails you can bring to your movie. ArcLight features a year-round mix of major blockbusters, independent films and documentaries as well as special screenings and events.
Remember the olden days when comedy clubs with a two-drink minimum policy ruled? That era is long gone, but this venerable laugh factory has managed to hang on. The comedy here is a bit of a mixed bag. On the one hand, Zanies offers stage time to up-and-comers while paying tribute to some of the greats, but both the venue and the comics can, at other times, feel a bit dusty.