Gay Games 2006 is over, but the gay spirit that infected Chicago in the summer of 2006 remains in the air. Chicago is still playing games with my heart.

Chicago, a north-south city sitting on the west coast of lake Michigan, offers gay diversions and passions like no other. Boystown remains the gay epicenter of Chicago, but rising real estate prices have stretched the strip northwards to Andersonville and Wicker Park.

Playing host to so many gay events, it’s difficult to pick a few. Chicago Gay Pride Parade in June is an annual event drawing an amazing 400,000 people to Boystown.

A unique street fair called Market Days is the largest two-day festival in Illinois. But early in its life the fair was nothing more than a few merchants on North Halsted. At that point the city refused to close off the street. In the mid 80’s a water pistol was shot at a passing bus, the driver, who had been shot, called the police who promptly closed the fair and unfairly arrested the shooters and on-lookers. Crowds gathered around the police station armed with water pistols demanding the release of their brothers and sisters. Next year the street was closed and the Market Days of today was created. Crafts, food, bands, beer, gay folks and water pistols line the streets in the hot August sun.

Andersonville holds it’s own version of Market Days, Andersonville Midsummerfest where 50,000 people gather on Clark Street to enjoy food, entertainment and crafts. Midsummerfest offers more family oriented fun.

While attending Midsummerfest only requires walking onto Clark Street, getting a plum spot at International Mr. Leather is not so easy. Early planning is essential for 2007 as the event is anticipated to draw record crowds to the city on Memorial Day weekend. That’s when leather men and women from around the world gather to crown a new International Mr. Leather. This leather / fetish party lasts nearly a week!


Locating Boystown is easy; simply find the 10ft tall gay rainbow pylons that mark off North Halstead between West Belmont and N. Broadway streets. The twenty rainbow pylons, a gift from the city in 1999, proudly bear witness to the influence the gay community has achieved in Chicago.

Boystown does its name justice when the sun sets. You will find large and small bars all along North Halstead. For dancing, stop in at Berlin (954 N. Halsted) or Cell Block (3702 N. Halsted). Berlin offers an amazing dance floor and a rotating schedule of DJ’s. Cell Block is not as intense and is more in tune with the leather crowd.

Sidetrack (3349 N. Halstead) continues to dominate over Boystown after 25 years and remains Chicago’s most popular gay bar - this huge complex of five bars is always packed. The video DJ is busy on the weekends spinning dance tunes, but turns his attention to show tunes on Sunday. The Sunday show tunes crowd is the party as everyone participates in the sing along, you can too.

More dancing can be found at Circuit/Rehab (3641 N. Halsted) and Hydrate (3458 N. Halsted). Circuit offers high-energy dancing to a Latin pop beat. Hydrate’s interior is lush and stylish, offering you a club atmosphere. Open later than most bars, a crowd draws as the night wanes.

If it’s a quieter good time you desire, head over to Gentry on Halsted (3320 N. Halsted) or Gentry on State (440 N. State) to enjoy the soothing sounds of jazz, piano or live-cabaret in a more laid back atmosphere.

A drag queen once told me in a drunken stupor, “You get a lot for your dollar at the Lucky Horseshoe Salon” (3169 N. Halsted) and the bitch was right! Every night male dancers dance, strip and tease the audience into an overheated state. Bring your dollar and they’ll make you holler!

North End (3733 N. Halsted) is famous as an original gay-sports bar. Which makes sense, as Boystown is located only blocks away from Wrigley Field. A simple layout offers televised sporting events, darts and pool.

More Boystown bars include: Cocktail (3359 N. Halsted), Manhandler (1948 N. Halsted), Minibar (3341 N. Halsted), Bucks (3439 N. Halsted), Bobby’s Love (3729 N. Halsted), Charlie’s (3726 Broadway), Kit Kat Lounge (3700 N. Halsted), and Little Jim’s (3501 N. Halsted).

Elsewhere in the city parties are getting started too. Crew Bar & Grill (4808 N. Broadway) is another sports bar with an upscale clientele. Watch your favorite team in HDTV as you munch on Crew food. An amazing 65 beer options are at your desire.

In Andersonville, N. Clark north of Lawrence Ave, you will find a lively leather / bear scene at Jackhammer (6406 N. Clark), Touche (6412 N. Clark) and Chicago Eagle (5015 N. Clark). As you can imagine, these three bars receive much of the attention during International Mr. Leather.

New this year is Hamburger Mary’s (5400 N. Clark St.) where you can “Eat, drink and be Mary!” Mary’s offers hamburgers and deserts along with a couple of surprises. Upstairs you will find Mary’s Attic where she has tucked away drag cabaret, karaoke and live music. This Mary has got it going on!

More Andersonville bars include: @tmosphere (5355 N. Clark), 3160 (3160 N. Clark), Star Gaze (5419 N. Clark), Clarks on Clark (5001 N. Clark), T’s Bar and Restaurant (5025 N. Clark).

A huge high-energy dance floor can be found at Crobar (1543 N. Kingsbury) on Sundays. A second story balcony gives you a nice perch over the dance floor to enjoy a spectacular show of hot, sweaty bodies moving to the music.

Big Chicks (5024 N. Sheridan) is a local favorite. This small, casual bar is often packed even during the week. Owner Michelle Fire hosts an always-crowded FREE bar-b-q on the outdoor patio every Sunday starting at 4PM.

Eats and of interest

Getting around Chicago is easy; just use the elevated subway called the El (for elevated). It’s best to buy a weeklong pass. Taxicabs are plentiful in Chicago too.

Stretching between Oak Street and the Chicago River on Michigan Ave, The Magnificent Mile offers a premium shopping experience. Visit many unique stores not found elsewhere, such as Nike’s Niketown, Apple’s flagship store, Nokia’s “Experience” where you can buy unlocked phones rarely seen in the US, and the Sony store. Also major clothing labels offer stores, such as Polo, Tommy Hilfiger and Prada. You can also find exaggerated versions of American favorites Banana Republic, Borders and Gap. Experience a one of its kind vertical mall at One Watertower Place (835 N. Michigan Ave). In the basement you will find Food Life a unique restaurant concept offering hundreds of American and ethnic food options in a park setting.

A not to be missed Café Iberico (739 N. LaSalle Dr.) will dazzle with its colorful style and superb Spanish tapas. Portillos (100 W. Ontario Street) is a must stop for a real taste of Chicago. Of special interest is the Italian beef sandwich, the chopped salad, and, of course, world-class Chicago hot dogs!!

What’s Chicago without pizza? While deep-dish pizza is a local favorite, Chicago Pizza and Oven Grinder (2121 N. Clark) has been offering something different since 1972. Inside you will find a traditional pub setting and a unique inverted pizza that is both delicious and memorable.

For coffee stop in at Intelligentsia Coffee (2123 N. Broadway), Uncommon Ground (3800 N. Clark), or Chicago Room Gallery Café (3318 N. Halsted) which includes a gallery space and outdoor patio. Popcorn, nuts and inspired gift ideas can be found at Nuts on Clark (3830 N. Clark Street). Sweet options include: Corner Bakery (9 Chicago locations), A Taste of Heaven (5401 N. Clark Street) and M. Henry Bakery (5797 N. Clark Street).

Ann Sathers (929 W. Belmont, 3411 N. Broadway or 5207 N. Clark) offers Swedish entrees in playful settings at reasonable prices. Known for Sunday breakfast, get there early to avoid the crowd.

Unabridged Books (3251 N. Broadway) is a serious bookstore. You will find a special emphasis to cater to the gay community with books and magazines. A gay friendly feminist bookstore Women and Children First (5233 N. Clark Street) also includes children’s books.

You will need to stop by Gay Mart (3457 N. Halsted) to find reading materials, cards and gifts of the gay persuasion. You can also find fun gay attire, toys and lubes here.

Getting Physical

Chicago offers three options for getting physical.

Steamworks (3246 N. Halsted) is located right in Boystown and offers a workout room, dry sauna, steam room, whirlpool, and video lounge. Steamworks is a large, clean and modern facility sure to impress.

Man’s Country (5017 N. Clark) offers a large steam room and whirlpool. Make sure to catch your favorite porn star live on stage after midnight on the weekends.

A bear crowd gathers at Man’s World (4862 N. Clark) where a safe environment leads to frisky encounters.

Additional diversions can be found at RAM Bookstore (3511 N. Halsted) offering gay porn and private booths, Banana Video (4923 N. Clark) with a porn video lounge and the Bijou Theater (1349 N. Wells). The Bijou Theater offers an intimate play space with a video lounge and private booths.