Exclusive | Three Gay Days: Chicago

Our travel guides are frequently updated. This guide was last updated 07/08. Still, there are places that are bound to have closed or changed since our last update. Use the listed phone numbers to call ahead, and please let us know of any corrections or new places of interest you discover.

Stretched along 19 miles of shimmering coastline at the southwest edge of the Great Lakes region and sprawling westward into the Midwestern prairie heartland, Chicago continues to surprise locals and visitors alike with a metropolitan safari of eye-popping architecture, internationally renowned museums, and a jumbled pastiche of fiercely territorial ethnic neighborhoods loosely stitched together by a common geography. What began as a humble outpost settled by French-Canadian fur traders in the mid-19th century became an overnight "instant" city where East Coast entrepreneurs saw before them the unlimited promises of the West.

Today, those promises have been fulfilled and Chicago has reaped the benefits of its founders. The city that birthed the skyscraper is often referred to as a "living museum." It boasts a collection of famed buildings by pioneers like Louis Sullivan, Daniel Burnham, and Frank Lloyd Wright, whose Prairie School homes and other buildings reflected the natural landscape. The skyline is dotted with icons like the Sears Tower and the John Hancock Building, not to mention recent additions by Rem Koolhaas and Frank Gehry.

The city's cultural life is well reflected in its diversity in the arts. The museum scene is dominated by heavyweights like the Shedd Aquarium and the Museum of Science and Industry and anchored by the magnificent Art Institute of Chicago. Jazz and blues have deep and lasting roots in Chicago and many live music venues have been around for decades. The Chicago Symphony Orchestra is nationally renowned, while house music, which originated here, is an integral part of the club landscape. The Chicago League of Theaters lists nearly 170 companies in its registry, including the Goodman and Steppenwolf Theaters as well as The Second City and i.O. (formerly Improv Olympic), launching pads for many past and present cast members of both SNL and MadTV.

Chicago's gay and lesbian population is large and highly visible. Lakeview, a.k.a. Boystown, one of two thriving gay neighborhoods in the city of Chicago, is located several miles north of the Loop in a triangle bounded by Belmont Avenue (3200 North), Halsted Street, and Broadway, which intersects both streets on its northwest path through the city. On Halsted Street, you'll find the highest concentration of queer activity.

Lesbians began settling in the Swedish immigrant neighborhood of Andersonville in the late '80s, and the last decade has seen a dramatic renovation of the entire area, which is now Chicago's second gay neighborhood. Restaurants, hip boutiques, and several bars are located along Clark Street between Foster Avenue and Bryn Mawr, but the attitude quotient here is sufficiently lower than in Boystown.

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