Chicago, Illinois • May 2 - 4, 2025
A Weekend created to kick off Leather Pride Month in Chicago, raise awareness of our Community, and fundraiser for the Leather Archives & Museum.
Chicago Leather Pride welcomes all gender identities, and all expressions of kink & fetish! Read more about this exciting event as recently published in The Reader
A Celebration of Leather Culture, Benefiting the LA&M.
SEE OUR FULL FINALIZED SCHEDULE BELOW!
Friday, May 2nd
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Friday, May 2nd *
Shop for Gear @ Full Kit Gear
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Happy Hour @ SoFo Tap
3 - 5pm
Start your Chicago Leather Pride Weekend early with some happy hour snacks and drinks. Then make sure you are geared up for the weekend before heading to our Leather Pride March!
Leather Pride March,
Bar Crawl, & Poker Run
4 - 8pm
Meetup starting at 4pm @ Barrelman Tavern
March Kicks off at 6PM Sharp with optional stops at Whiskey Girl Tavern, Jackhammer, Leather 64Ten, Touche, and convene at LA&M at 8:15pm). All Gender Identities and Expressions of Leather, Fetish, and Kink are Welcome!
Poker Run - Buy in with 2 Cards to start, and collect more at each stop the way. Prize to the best of 5 (8 total possible) hand at the Opening Reception!
CLPW Opening Reception
@ Leather Archives & Museum
8:30 - 10pm
Fetish Night Out
@ Jackhammer, Touche, or Cell Block; Wherever Tickles your fancy!
10pm – 4am
Friday Bootblack Schedule:
Tito Joey
7 - 10pm @ LA&M
Saturday, May 3rd
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Saturday, May 3rd *
Breakfast with WTNB - Women, Trans, & Nonbinary, Leather/Kink Social
@ LA&M
9am - Noon
Fetish, Erotic, Kink Figure Drawing Open Studio
@ LA&M
10:30 - Noon
We'll provide the sexy fetish models, tables and chairs......you provide whatever materials you want to use for your art.
Fetish Photography
@ LA&M
11am - 1pm
Open to ALL!
Pork ‘N Puff; Cigars & BBQ Fundraiser
@ LA&M
12 - 2pm
Hosted by Vince Jay, Mr. Chicago Leather 2024. Come socialize while enjoying cigars, savory smoked meats, and delicious sides.
Bake Sale w/ the Second City Sisters, Abbey of the Irreverent Bean
@ LA&M
12 - 3pm
Come donate for delicious baked treats from our Second City Sisters, Abbey of the Irreverent Bean!
Vespertine: Takeover The Hole
@ Jackhammer
2 - 4pm
Vespertine Chicago is excited to invite you to our very 1st day time event!! In partnership with The Jackhammer and Chicago Leather Pride Weekend Vespertine Chicago will TAKE OVER THE HOLE on Saturday May 3rd from 2-4pm. This event will benefit The Leather Archives & Museum and is an official event of Chicago Leather Pride Weekend.
Vespertine Chicago is open to all Queer Women, Transfolx, and Non-Binary Folx 21 years of age and older. If you are TransMasc and still feel an affinity for the Queer Women's Community we would love to welcome you. NO CIS MEN ALLOWED.
Vespertine Chicago encourages education in the fine Fetish arts, with interactive hands on learning, safe and consensual scene play, all while encouraging a person to explore new and exciting ways to express themselves through BDSM and Fetish.
ABSOLUTELY NO LATEX PLEASE- HOST HAS EXTREME ALLERGY
Restrictions:
Valid State ID REQUIRED. The Hole is a 21+ Venue.
Drugs use will not be tolerated, and is grounds for immediate dismissal without refund for all Vespertine Chicago Events
NO PHOTOGRAPHY or phone use in the play space, please.
Launch & Lick: A Pie Throw Fundraiser for LA&M
@ LA&M
2 - 3:30pm
Hosted by: Dustin James & Gary Wasdin. Free to attend! Donate to throw pies and lick ‘em clean!
Leather Jeopardy w/ boy Paul
@ LA&M
4 - 6pm
Family Dinner
@ LA&M
5 - 7pm
Fetish Follies: a Cabaret Fundraiser for LA&M
@ LA&M
7 - 9pm
Belly Up!
@ Jackhammer
9pm - 5am
L.O.A.D.
@ Cellblock
9pm - 3am
Nite of 1000 Tailz
@ The Baton Show Lounge
11pm - 4am
Saturday Bootblack Schedule:
Finch
11am - 4pm @ LA&M
Tito Joey
4 - 9pm @ LA&M
Sunday, May 4th
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Sunday, May 4th *
Breakfast with WTNB - Women, Trans, & Nonbinary, Leather/Kink Social
@ LA&M
9am - Noon
Sausage and Cigar Social
@ Jackhammer
Noon - 3pm
Harm Reduction and Chemsex Class by Chicago Recovery Alliance
@ LA&M
1:30 - 2:45pm
This interactive discussion will provide a foundational understanding of harm reduction principles and their application in chemsex (the use of drugs to enhance sexual experiences). We will explore ways to reduce risks, promote safer use, and challenge the stigma surrounding drug use and sexuality. Participants will learn practical strategies for setting boundaries, managing consent, and practicing safer substance use, including the proper use of naloxone for opioid overdose reversal, fentanyl and drug-checking test strips, and Doxy PEP (doxycycline post-exposure prophylaxis) for STI prevention. This session offers a non-judgmental space for service providers, community advocates, and those with lived experience to engage in real-world approaches to making chemsex safer, healthier, and more affirming.
C.O.D.E. Sunday Funday
@ The Baton Show Lounge
2 - 6pm
Fire Flogging with Master Leather Redux
@ LA&M
3 - 4:30pm
Shop for Gear @ Men’s Room
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Gear Tunes @ Sidetrack
5 - 9pm
Sunday Bootblack Schedule:
Finch
12 - 3pm @ Jackhammer