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Chicago Gay Travel Guide

Gay Chicago Bars, Restaurants and Clubs

Gay Friendly and Gay Chicago Hotels

Chicago Gay Pride and other Gay Events

Life in the Windy City is all about hard work, deep-dish pizza, and lake-effect snow. Chicago is a working-class city, and this can be felt from street-side diners to the dance floors of gay clubs. That means friendliness to the nth degree. Ask any gay man in the city if he knows where Oprah lives, and he will offer to show you! (Of course, after several guys have taken you to several different houses, each swearing that it’s Oprah’s pad, you’ll learn to phase out the city’s obsession with their Diva Darling of TV Talk.) But on the backs of these dedicated workers have been built no fewer than two of the world’s tallest buildings, the Sears Tower (tallest in America for all you size queens!) and the slightly shorter John Hancock Center. If you’re an architecture bug, check out the Frank Lloyd Wright home and studio, where he lived for 20 years. The Windy City’s many museums beckon, The Art Institute of Chicago and the Museum Campus, which includes the Field Museum of natural and cultural history, the Shedd Aquarium, and the Alder Planetarium and Astronomy Museum, all nestled around a lovely park. If your wallet feels too fat, head to the Navy Pier for shopping, dining, and people watching. (Just don’t get your hopes up for seeing too many Navy boys in their white sailor suits!) For you hardcore shopping junkies, The Magnificent Mile will max your credit cards in a heartbeat. Getting to and from everything is simple and cheap on “The El,” Chicago’s subway and “El”evated trams. When you’re ready for a gayer crowd, Boystown is your spot, just north of downtown at the Belmont El-stop along Halsted Street. Chicago’s famous leather scene is centralized further north in the Andersonville area, along with a handful of lesbi-gay venues. In the summer, everyone flocks to Hollywood Beach, north of town, for volleyball and sunning.

Gay Chicago Bars, Restaurants and Clubs

A stroll up and down Halsted Street between Fletcher and Waveland will reveal 90% of Chicago’s gay scene. Bobby’s Love, a popular local’s bar, is a great place to experience the amazing friendliness of Chicago folk. The Lucky Horseshoe Lounge, at the opposite end of Boystown, is extremely popular for its go-go boys, though Madrigal’s up in Andersonville attracts a wider range of ages to gawk at its dancers. Gentry is a piano bar with two locations, Gentry on State in downtown and Gentry on Halsted. Cocktail attracts a big crowd of friendly boys and girls. For something more chic and snobby, hit Felt. Roscoe’s Tavern offers everything from pool to drag. The Closet in Andersonville is where the girls flock. Also in that part of town can be found Big Chicks, not a lesbian venue despite the name. It attracts a friendly local crowd. @tmosphere is a chic alternative . If a sports bar is more your speed, try the famous North End or the newer Crew. Chicago’s leather scene is more developed than in most big cities. Up in Andersonville, check out Touché, Chicago’s oldest, Jackhammer, or the Eagle, all with infamous darkrooms. But if you’re in Boystown and can’t get all the way up there, you can duck into the Cellblock, but you’ll need to be in full leather gear to get beyond the first room!

When you’re ready for some serious clubbing, Chicago’s got a lot to offer. In Boystown, try Berlin, which is so intense it has a loyal hetero following as well. Circuit draws a younger crowd. Hydrate is the newest club on the scene, and is always packed. Spin draws a friendlier crowd than most gay discos. Up in Andersonville, the girls dance at Star Gaze, and the late-night Charlie’s appeals to the two-stepping crowd. In downtown, Sound-Bar promises to revolutionize the clubbing experience, and draws a mixed crowd. Crobar is where everyone flocks on Sunday night for GLEE club, the longest-running gay dance party in America.

All that dancing will work up a hunger. Roscoe’s is probably the most popular gay place to chow down while watching the pretty people walk up and down the sidewalk. Nookies Tree serves a popular breakfast. Jack’s, though, is the place for pricey Sunday brunch, complete with live jazz. There are dozens of restaurants in the Boystown strip, pick your cuisine (or your crowd) and get to munchin’. Big Chicks in Andersonville also has a fairly extensive menu.

Gay Friendly and Gay Chicago Hotels

The Villa Toscana is Chicago’s most famous gay hostelry, right in the center of Boystown. Each room has a different ethnic flair (try Moroccan or French). The gay-owned Ardmore House Bed and Breakfast is removed from the gay scene, but a few blocks from the gay beach. Beyond that, you’re limited to mainstream hotels. The Best Western Hawthorne Terrace is convenient to Andersonville and usually has a high percentage of gay guests.

Call an edirp.com gay travel specialist at 1-888-EDIRP-EZ (1-888-334-7739) or (214) 520-0345 (U.S.) to book any of the hotels mentioned above. Any hotels with links may be booked via our secure online booking system.

Chicago Gay Pride and other Gay Events

Chicago Pride is a huge event, with activities spanning the entire month of June. It usually culminates with a parade on the final Sunday in June. The International Mr. Leather competition always chooses Chicago as the locale for its ultimate competition, held at the Chicago Eagle each year on Memorial Day weekend.

Travel guide by Benjamin Starr, a travel writer who claims the entire world as his home.  When he's not at home, he can sometimes be found at a residence in Dallas, Texas. To contact Ben, email him at benjaminstarr@sbcglobal.net.

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