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: Andersonville, Boystown, Lake View, Rogers Park, Uptown
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, Boystown) A bar in Boystown with porn in the back. Check out the website to see what’s going on in the back room. 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
Meeting House Tavern (5025 N Clark St, Uptown) Leather-friendly bearish bar. 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
WHERE TO FUCK
Cell Block (3702 N Halsted St, Boyston) Check out the website to see what’s going on in the back room. link
CODE Night (4703 N Broadway, Uptown) Chicago Original Dresscode Enforced. Monthly dance & fuck parties in a future home of the Chicago Eagle. link
Steamworks Baths (3246 N Halsted St, Boystown) Local outpost of the international chain of bathhouses. link
WHERE TO SHAKE YOUR ASS (AND CRUISE)
Brüt Dance parties for guys in gear. link
Cell Block (3702 N Halsted St, Boyston) Check out the website to see when the DJ will be on the decks. link
CODE Night (4703 N Broadway, Uptown) Chicago Original Dresscode Enforced. Monthly dance & fuck parties in a future home of the Chicago Eagle. link
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
Brown Elephant (5404 N Clark St, Andersonville) Browse the racks at this thrift shop for bargains on used leather. Proceeds go to services including LGBTQ+ healthcare. 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
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
Red Vault (6534 N Clark St, Rogers Park) Chicago’s newest shop for fetishwear, toys, and more. link
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
The Den Off Eastlake (7601 N Eastlake Ter, Rogers Park) A clothing-optional B&B for men with private access to 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
WHERE TO EAT (AND CRUISE)
Ann Sather (3415 N Broadway, Boystown/Lake View) Yummy Swedish breakfasts in Boystown. link
Big Gay Sal’s Pizza (3445 N Halsted, Boyston) Grab a slice in the heart of Boystown. Hang out on the outdoor patio in good weather. 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
My Buddy’s (4416 N Clark St, Uptown) Fetish-friendly saloon for casual dining. 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
WHERE TO PUMP IRON (AND CRUISE)
Cheetah Gym (5248 N Clark, Andersonville) Possibly Chicago’s most gay-friendly gym. link
FFC East Lakeview (3657 N Pine Grove Ave, Lake View) Huge gym with group fitness classes, an indoor gym, and more. link
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
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
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
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
Chicago Spanking Party Men spanking men in Chicagoland. link
Galleria Domain Two A pansexual BDSM club with a dungeon. link
Hand Ball Chicago Chicago fisters. 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
WHAT TO SEE WHILE YOU’RE IN TOWN
AIDS Garden Chicago (South of Belmont Harbor) A monument created to memorialize the early days of Chicago’s HIV epidemic and to honor those who continue to fight against the disease today. The monument is at the site of the old Belmont Rocks cruising area and features a 30-foot Keith Haring sculpture. link
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
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
Chicago Leather Pride Weekend IML isn’t the only Leather event going on in Chicago in May. link
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
Chicago Fetish Weekend Celebrating Chicago’s diverse fetish community. 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
[Suggestions? Corrections? Contact me!]