CHICAGO

The City of the Big Shoulders.  The Windy City.  And it’s not just the wind that’s blowing.  The home of IML.  Leather Central in the center of the States.

Hot-spot neighborhoods:  Boystown, Lake View, Rogers Park

Drink  Fuck  Shake  Buy  Crash  Eat  Pump  Trim  Ink  Hang  See  Plan

WHERE TO DRINK (AND CRUISE)

Big Chick’s (5024 N Sheridan Rd, Margate Park) A leather-friendly neighborhood bar particularly popular on Thursdays (Bear Den every 3rd Thursday) and Fridays.  link

Cell Block (3702 N Halsted St, Boyston) A bar in Boystown with porn in the back.  Dress code enforced in the back for CODE Night on first Saturdays.  link

The Granville Anvil (1137 W Granville Ave, Edgewater) Dive bar on the Far North Side that gets major points for the clever name.  link

The Hole (6406 N Clark St, Rogers Park) Downstairs at the Jackhammer is the total pig-fest appropriately named The Hole with strict dress-code policies on weekends.  link

The Jackhammer Complex (6406 N Clark St, Rogers Park) A dancey bar for Leathermen and bears.  link

Sidetrack (3349 N Halsted St, Boystown) Very leather-friendly Boystown bar with extremely popular Show Tunes on Sundays.  link

The SoFo Tap (4923 N Clark St, Uptown) A leather-friendly neighborhood bar SOuth of FOster with an outdoor patio that packs ’em in in the summer.  link

Touché (6412 N Clark St, Rogers Park) Chicago’s classic leather bar, since 1977.  link

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WHERE TO FUCK

Steamworks Baths (3246 N Halsted St, Boystown) Local outpost of the international chain of bathhouses.  link

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WHERE TO SHAKE YOUR ASS (AND CRUISE)

Brüt  Dance parties for guys in gear.  link

Man Upp  Dance parties for DILFs.  link

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WHERE TO BUY GEAR

The Alley Chicago (2620 W Fletcher St, Avondale) Get leather and more at this historic store serving the counterculture.  link

Army Navy Sales (3100 N Lincoln Ave, Lake View) A wonderland of military merchandise in Lake View.  link

Carhartt – Gurnee Town Center (7055 W Grand Ave, Gurnee) For classic work gear.  link

Carhartt – Wicker Park (1518 N Milwaukee Ave, Wicker Park) For classic work gear.  link

Cram Fashion (3331 N Broadway, Boystown) Fun, casual fashions in Lake View.  link

Cupid’s Leather Sport (3503 N Halsted St, Boystown) A sex shop in Boystown.  link

Full Kit Gear (5021 N Clark St, Uptown) A shop for serious Leathermen.  link

LEATHER64TEN (6410 N Clark St, Rogers Park) A gear and sex shop adjoining the Jackhammer.  link

The Men’s Room (3420 N Halsted St, Boystown) Butch fashions in Boystown.  link

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WHERE TO CRASH (AND MAYBE FUCK SOME MORE)

Best Western Plus Hawthorne Terrace (3434 N Broadway, Boystown) The international chain’s outpost in Boystown.  link

City Suites Hotel (933 W Belmont Ave, Boystown/Lake View) An Art Deco property proud of its Boystown location.  link

The Congress Plaza Hotel (520 S Michigan Ave, South Loop) Chicago’s dumpy grand dame and legendary home of IML.  Across the street from Grant Park and Lake Michigan.  link

Hampton Inn Majestic Chicago Theatre District (22 W Monroe St, The Loop) Popular alternative to the Congress for IML.  link

Heart O’ Chicago Motel (5990 N Ridge Ave, Edgewater) Cheap, sorta sleazy motel close to the leather bars.  link

Hilton Chicago (720 S Michigan Ave, South Loop) Popular alternative to the Congress for IML.  link

Hotel Versey (644 W Diversey Pkwy, Lake View) Hip boutique hotel just off Clark.  link

Hotel Zachary (3630 N Clark St, Wrigleyville) Newly opened hip property across from Wrigley Field, not far from Boystown bars.  link

Majestic Hotel (528 W Brompton Ave, Lake View) Boutique hotel meets English-style estate.  link

The Villa Toscana (3447 N Halsted St, Boystown) A Victorian B&B in the heart of Boystown.  link

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WHERE TO EAT (AND CRUISE)

Ann Sather (3415 N Broadway, Boystown/Lake View) Yummy Swedish breakfasts in Boystown.  link

D.S. Tequila Company (3352 N Halsted St, Boystown) Get a head-start on your night out with tequila drinks at this popular Tex-Mex place.  link

Kanela Breakfast Club (5413 N Clark St, Andersonville) Breakfast spot popular with local Leathermen.  link

Lady Gregory’s (5260 N Clark St, Andersonville) Irish pub in Andersonville.  link

Lark (3441 N Halsted St, Boystown) Wood-fired pizza and more in Boystown.  link

Tweet (5020 N Sheridan Rd, Margate Park) Comfort food located adjacent to Big Chick’s.  link

Wood (3335 N Halsted St, Boystown) A stylish dining spot with craft cocktails.  link

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WHERE TO PUMP IRON (AND CRUISE)

Lakeview Athletic Club (3212 N Broadway, Boystown) A full-service gym in Boystown with a rooftop pool.  link

Quads Gym (3727 N Broadway, Boystown/Lake View) A no-frills gym for the most serious musclemen.  link

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WHERE TO GET A BUZZ CUT AND BEARD TRIM

Father & Son Barber Shop (5806 N Broadway, Magnolia Glen) Haircuts for Daddies and boys.  link

The Men’s Room (3420 N Halsted St, Boystown) Get in some grooming while you’re getting in some shopping.  link

Philip B Studio 24 (2945 N Broadway, Boystown/Lake View) Philip is the favorite barber for many Leathermen.  He cuts hair at his shop and also every 3rd Saturday at Touché.  link

Slade’s Barbershop (3314 N Halsted St, Boystown) Barbers in Boystown.  link

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WHERE TO GET INKED

Head 2 Toe Studios (3008 W Lawrence Ave, Albany Park) A tattoo and piercing studio popular with the Leather community.  link

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WHO TO HANG WITH

BLUF Chicago  For men into full dress leather uniform.  link

Chicago Gay Bikers  The name says it all.  link

Chicago Hellfire Club  World-renowned BDSM club.  link

Galleria Domain Two  A pansexual BDSM club with a dungeon.  link

LRA  A pansexual organization for alternative expressions of sexuality.  link

Masters And slaves Together:  Gurnee  Local branch of the organization for those who live the lifestyle.  link

Motor Bearz  Gay bikerz in the Chicago area.  link

ONYX Midwest  A club for Leathermen of color.  link

The Next Generation Chicago  A BDSM education group for members 18-35.  link

Trident International Windy City A pansexual Leather social organization.  link

Windy City boys Troop  A club for Leather boys.  link

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WHAT TO SEE WHILE YOU’RE IN TOWN

Leather Archives & Museum (6418 N Greenview Ave, Rogers Park) The must-see galleries of the history and culture of the Leather community.  link

The Legacy Walk (N Halsted St, Boystown) A walk up Halsted featuring “Rainbow Pylons” embedded with plaques honoring noteworthy LGBT individuals.  link

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WHAT TO PLAN FOR

January

Mr. Chicago Leather  An annual leather contest held at the Leather Archives & Museum and hosted by Touché.  (Check Touché’s website for details.)  link

March

Mr. LEATHER64TEN Contest  Find out which hot Leatherman will win this coveted title and go on to vie for IML.  link

May

International Mr. Leather  Perhaps you’ve heard of it?  Find out who in the world is the ultimate Leatherman.  link

June

Chicago Pride  Join the Chicago Leather/Fetish Pride group in the parade.  link

July

American Brotherhood Weekend  Celebrating the American Leather Family.  link

August

Bootblack Round Up  An event for bootblacks to call their own!  link

Northalsted Market Days  Enormous street festival that attracts Leathermen, big-name talent, and just about everyone else.  link

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[Suggestions?  Corrections?  Contact me!]