
Upcoming events
Events in The Hole include in-house and third-party local/international fetish events and our weekly events: STRAP’N, Fetish Friday and Cruise. With its late-night license, The Hole is the go-to bar for the LGBTQIA+ community until 4am (5am on Saturdays). Check back here for details on upcoming events in The Hole!
Dress Code Encouraged


THE KENNEL
The pack is gathering—are you ready to run wild? Get lost in the beats, the energy, and the thrill of the night with an electrifying lineup of DJs and hosts.

Belly Up
Join us on Sat, Apr 5th, starting at 9pm for a night of bringing together chubs, chasers, bears, gainers, encouragers, and admirers. Dance the night away with music from DJs Jesse Mercado, Robert Ratola and Club Chow in a fun, inclusive space that appreciates big bellies and chubby folks.
Big Bears, Beautiful Bellies, and their admirers—come together and enjoy! 🐻

Cruise
Flag it. Find it. Cruise The Hole—Sunday nights from 9pm–4am. Grab your hanky and Cruise.


STRAP'N
The Hole brings you the sexiest and most exhilarating jockstrap and jillstrap night in town with STRAP'N. Flaunt your hottest jock or jill straps, leaving little to the imagination! The Hole's infamous Pit opens up, inviting you to explore your deepest desires and indulge in the most exhilarating sensations. It's time to surrender to the thrill and let your inhibitions run wild!

SMOOCH
The music is mighty, consent is hawt, and kissing is key at 💋 SMOOCH 💋 . Spend the evening sharing some of your liplockable lust with someone in a snog or three in our kissing booth. Plus, candy treats for all!
We've got two levels of music, a house vibe upstairs and a techno vibe downstairs, to inspire your particular mood, get you moving and make your move.

MEGAWOOF CHICAGO
Come join us for a paw-some time at Jackhammer!
The 🐻🐻 BEARS OF MEGAWOOF are BACK🐻🐻
Saturday, April 12th, from 9pm to 5am
Another Great Team is waiting for you with Special



Fetish Friday: Gear
GEAR up and get into Jackhammer for Fetish Friday: GEAR, every 3rd Friday of the month. GEAR is dedicated to showcasing your hoods, harness, leather and rubber (and everything in between). Whether you've got a collection or are trying out your first piece, GEAR is here to encourage you to embrace, celebrate and explore the scene.

FREAQ
🔥 Step into the shadows and turn up the heat—FREAQ returns to Jackhammer and The Hole for a night of scandalous beats, tantalizing moves, and full-venue indulgence.
Slip into something scandalous or strip down to almost nothing—it’s your time to shine, seduce, and dominate the night. Let’s make this a FREAQ to remember. 🖤

Cruise
Flag it. Find it. Cruise The Hole—Sunday nights from 9pm–4am. Grab your hanky and Cruise.


STRAP'N
The Hole brings you the sexiest and most exhilarating jockstrap and jillstrap night in town with STRAP'N. Flaunt your hottest jock or jill straps, leaving little to the imagination! The Hole's infamous Pit opens up, inviting you to explore your deepest desires and indulge in the most exhilarating sensations. It's time to surrender to the thrill and let your inhibitions run wild!

Fetish Friday: Bark After Dark
Unleash your inner canine at BARK AFTER DARK! This unique event brings together pup play enthusiasts for an evening of lighthearted discovery every fourth Friday of the month at Jackhammer. Embrace your inner trainer or puppy and join us for an unforgettable experience that will set your tail wagging and your heart racing.

Cruise
Flag it. Find it. Cruise The Hole—Sunday nights from 9pm–4am. Grab your hanky and Cruise.


NIGHT OF 1000 DJ GAYBASH
@putopiacollective & @spiral_productions93 presents NIGHT OF 1000 DJ GAYBASH!
In celebration of @djgaybash ‘s birthday, we invite you all to come dressed as DJ GayBash! @sandler.tdy , @bilatinbby , @jsbxse , and @juan.aka.grizzly join Bash on the decks for a night of b2b’s. Hosting the night will be @mister_hoochiemama , serving a HoochieBash! fantasy! See you there!
March 30th, 9p-3:30a @jackhammer_chicago (in @thehole_chicago)
🌗 SUNDAY SPECIALS
$7 Jackhammered Long Islands
HOUSE RULES
🔩 All bags/fanny packs/purses/etc. are subject to search
🔩 Gear encouraged, but not required
🔩 Clothes Check available
🔩 NO CAMERAS in The Hole
🔩 EVERYONE is welcome at Jackhammer regardless of color, size, body type, ability, gender expression(s) and/or sexual orientation. Bigotry of any kind is not tolerated and is grounds for removal from the space.
We are a 21+ Venue, you must present a valid government-issued ID for entry.
No outside beverages or liquids are permitted in 2Bears Tavern Group bars at any time.
EMBRACE | CELEBRATE | EXPLORE

Diaper Up: Neon
DIAPER UP: NEON
A Glow-in-the-Dark Playground!
🗓 Date: Saturday March 29th
⏰Time: 9pm - 5am
Get ready to light up the night at Diaper Up: Neon! This month, we’re turning the dance floor into a UV wonderland, where your neon onesies, glowing pacis, and cuddly plushies shine under black lights! Whether you’re here to dance, play, or just bask in the glow, this is your night to let loose and have fun.
🎶 MUSIC BY 🎶
Man In Uniform (U.K.) – Bringing high-energy, pulsing basslines straight from the UK, Man In Uniform will keep the dance floor moving all night with hard-hitting techno. Get ready for deep, driving rhythms and hypnotic beats that will pull you into the neon-lit night.
✨ DOOR COVER ✨
Before 10pm: FREE
10pm-2am: $10
2am-Last call: $5
🍹 SATURDAY SPECIALS 🍹
$3 House Shots
$5 Miller Lite Tallboys
🪩 WHAT TO EXPECT 🪩
🩵 DJ spinning high-energy beats to keep you waddling
💚 UV lights & glow decor to make everything pop
🩷 Photo booth to capture your brightest moments
🧡 Coloring station for a creative break
💜 Changing area sponsored by Northshore Care & Tykables
💛 Glow-in-the-dark sippy cup cocktails to sip in style
👠 WHAT TO WEAR 👠
The brighter, the better! Neon, UV-reactive outfits, onesies, pacis, plushies—whatever makes you feel cute, comfy, and ready to shine!
*Not required
🚦 CONSENT & RESPECT 🚦
Diaper Up is a judgment-free, inclusive space where respect and consent are non-negotiable. Play, dance, and interact only with enthusiastic consent—no exceptions. Harassment, inappropriate behavior, or violating boundaries will not be tolerated. Our staff and community are here to ensure everyone has a safe and fun experience. If you ever feel uncomfortable, please reach out to event staff immediately.
Diaper Up event staff will be wearing yellow branded lanyards with name badges. Please report issues to the bar staff if you cannot locate Diaper Up staff.
HOUSE RULES:
🔩 All bags/fanny packs/purses/etc. are subject to search
🔩 Gear encouraged, but not required
🔩 Clothes Check available
🔩 NO CAMERAS in The Hole
🔩 EVERYONE is welcome at Jackhammer regardless of color, size, body type, ability, gender expression(s) and/or sexual orientation. Bigotry of any kind is not tolerated and is grounds for removal from the space.
We are a 21+ Venue, you must present a valid government-issued ID for entry.
No outside beverages or liquids are permitted in 2Bears Tavern Group bars at any time.
EMBRACE | CELEBRATE | EXPLORE

Fetish Friday: Bark After Dark
Unleash your inner canine at BARK AFTER DARK! This unique event brings together pup play enthusiasts for an evening of lighthearted discovery every fourth Friday of the month at Jackhammer. Embrace your inner trainer or puppy and join us for an unforgettable experience that will set your tail wagging and your heart racing.
🎟️ COVER:
Before 10pm: FREE
10pm-2am: $10
2am-Last call: $5
🌗 FRIDAY SPECIALS
$5 Miller Lite Tallboys
$8 New Amsterdam & Red Bulls
HOUSE RULES:
🔩 All bags/fanny packs/purses/etc. are subject to search
🔩 Gear encouraged, but not required
🔩 Clothes Check available
🔩 NO CAMERAS in The Hole
🔩 EVERYONE is welcome at Jackhammer regardless of color, size, body type, ability, gender expression(s) and/or sexual orientation. Bigotry of any kind is not tolerated and is grounds for removal from the space.
Fetish Friday is a weekly event from 9pm–4am that features rotating themes and parties. Participation in themes is totally optional and accessible to all—from newbies to the more experienced—and intended to encourage guests that are interested in the theme to explore and learn in a safe, LGBTQIA+ environment.
We are a 21+ Venue, you must present a valid government-issued ID for entry.
No outside beverages or liquids are permitted in 2Bears Tavern Group bars at any time.
EMBRACE | CELEBRATE | EXPLORE

STRAP'N
The Hole brings you the sexiest and most exhilarating jockstrap and jillstrap night in town with STRAP'N. Flaunt your hottest jock or jill straps, leaving little to the imagination! The Hole's infamous Pit opens up, inviting you to explore your deepest desires and indulge in the most exhilarating sensations. It's time to surrender to the thrill and let your inhibitions run wild!
We've got you uncovered with our FREE clothes check, so you can let go of inhibitions and fully immerse yourself in the electrifying atmosphere without any distractions.
Get STRAP’N and grab your sexiest jockstrap or jillstrap and join us for a night of unforgettable fun! **Dress code is not required but encouraged.**
🌗 THURSDAY SPECIALS
$3 House Shots
$5 New Amsterdam Cocktails
$5 Miller Lite Tallboys
HOUSE RULES
🔩 All bags/fanny packs/purses/etc. are subject to search
🔩 Gear encouraged, but not required
🔩 Clothes Check available
🔩 NO CAMERAS in The Hole
🔩 EVERYONE is welcome at Jackhammer regardless of color, size, body type, ability, gender expression(s) and/or sexual orientation. Bigotry of any kind is not tolerated and is grounds for removal from the space.
We are a 21+ Venue, you must present a valid government-issued ID for entry.
No outside beverages or liquids are permitted in 2Bears Tavern Group bars at any time.
EMBRACE | CELEBRATE | EXPLORE


Cruise
Dive into The Hole every Sunday from 9pm–4am for CRUISE, where you can flag a hanky or discover a new kink in a safe and discreet atmosphere. Keep those eyes peeled and those desires hard all night long.
🌗 SUNDAY SPECIALS
$7 Jackhammered Long Islands
HOUSE RULES
🔩 All bags/fanny packs/purses/etc. are subject to search
🔩 Gear encouraged, but not required
🔩 Clothes Check available
🔩 NO CAMERAS in The Hole
🔩 EVERYONE is welcome at Jackhammer regardless of color, size, body type, ability, gender expression(s) and/or sexual orientation. Bigotry of any kind is not tolerated and is grounds for removal from the space.
We are a 21+ Venue, you must present a valid government-issued ID for entry.
No outside beverages or liquids are permitted in 2Bears Tavern Group bars at any time.
EMBRACE | CELEBRATE | EXPLORE

BUTCH PLEASE: Get Lucky
Get ready to sweat, strut, and serve at BUTCH PLEASE, where the music is pounding, the leather is gleaming, and the energy is undeniable. This is not your average night out—it’s a full-throttle, high-voltage queer takeover of the dance floor!
🎧 Beats by:💥Mister Hoochiemama – Bringing the filth, funk, and fire 🔥 Vitigrrl – Spinning beats to make your boots stomp 💣GayBash! – Smashing the status quo, one banger at a time
🎤 Hosted by: 💋Darling Squire – Your guide to a night of pure queer revelry
Dress code? Leather, latex, harnesses, lace, jockstraps, pasties—whatever makes you feel powerful, sexy, and unapologetically YOU.
Expect high-energy beats, low inhibitions, and a dance floor packed with the hottest queers in town. Whether you're a seasoned kinkster, a baby butch, or just here for the vibes, this is your night to be free, wild, and wicked.
✨ Come for the music, stay for the mischief.✨
COVER:
💄💋FREE ENTRY BEFORE 10 PM💋💄
⚡️$10 AFTER 10PM⚡️
🌗 SATURDAY SPECIALS:
$3 House Shots
$5 Miller Lite Tallboys
HOUSE RULES:
🔩 All bags/fanny packs/purses/etc. are subject to search
🔩 Gear encouraged, but not required
🔩 Clothes Check available
🔩 NO CAMERAS in The Hole
🔩 EVERYONE is welcome at Jackhammer regardless of color, size, body type, ability, gender expression(s) and/or sexual orientation. Bigotry of any kind is not tolerated and is grounds for removal from the space.
We are a 21+ Venue, you must present a valid government-issued ID for entry.
No outside beverages or liquids are permitted in 2Bears Tavern Group bars at any time.
EMBRACE | CELEBRATE | EXPLORE

Fetish Friday: Gear
GEAR up and get into Jackhammer for Fetish Friday: GEAR, every 3rd Friday of the month. GEAR is dedicated to showcasing your hoods, harness, leather and rubber (and everything in between). Whether you've got a collection or are trying out your first piece, GEAR is here to encourage you to embrace, celebrate and explore the scene.
🎟️ COVER:
Before 10pm: FREE
10pm-2am: $10
2am-Last call: $5
🌗 FRIDAY SPECIALS
$5 Miller Lite Tallboys
$8 New Amsterdam & Red Bulls
HOUSE RULES:
🔩 All bags/fanny packs/purses/etc. are subject to search
🔩 Gear encouraged, but not required
🔩 Clothes Check available
🔩 NO CAMERAS in The Hole
🔩 EVERYONE is welcome at Jackhammer regardless of color, size, body type, ability, gender expression(s) and/or sexual orientation. Bigotry of any kind is not tolerated and is grounds for removal from the space.
Fetish Friday is a weekly event from 9pm–4am that features rotating themes and parties. Participation in themes is totally optional and accessible to all—from newbies to the more experienced—and intended to encourage guests that are interested in the theme to explore and learn in a safe, LGBTQIA+ environment.
We are a 21+ Venue, you must present a valid government-issued ID for entry.
No outside beverages or liquids are permitted in 2Bears Tavern Group bars at any time.
EMBRACE | CELEBRATE | EXPLORE


Cruise
Flag it. Find it. Cruise The Hole—Sunday nights from 9pm–4am. Grab your hanky and Cruise.
🌗 SUNDAY SPECIALS
$7 Jackhammered Long Islands
HOUSE RULES
🔩 All bags/fanny packs/purses/etc. are subject to search
🔩 Gear encouraged, but not required
🔩 Clothes Check available
🔩 NO CAMERAS in The Hole
🔩 EVERYONE is welcome at Jackhammer regardless of color, size, body type, ability, gender expression(s) and/or sexual orientation. Bigotry of any kind is not tolerated and is grounds for removal from the space.
We are a 21+ Venue, you must present a valid government-issued ID for entry.
No outside beverages or liquids are permitted in 2Bears Tavern Group bars at any time.
EMBRACE | CELEBRATE | EXPLORE

FREAQ
🔥 Step into the shadows and turn up the heat—FREAQ returns to Jackhammer and The Hole for a night of scandalous beats, tantalizing moves, and full-venue indulgence.
Slip into something scandalous or strip down to almost nothing—it’s your time to shine, seduce, and dominate the night. Let’s make this a FREAQ to remember. 🖤
DJs
🔊 Mister Hoochiemama
🔊 Josh Steers
🔊 La Spacer
Hosts
✨ Lilith Towers
✨ Scruffy
✨ Nico
Produced by Spiral Records
Cover:
Before 10pm: Free
10pm - 2am: $10
2am - Close: $5
🌗 SATURDAY SPECIALS:
$3 House Shots
$5 Miller Lite Tallboys
HOUSE RULES:
🔩 All bags/fanny packs/purses/etc. are subject to search
🔩 Gear encouraged, but not required
🔩 Clothes Check available
🔩 NO CAMERAS in The Hole
🔩 EVERYONE is welcome at Jackhammer regardless of color, size, body type, ability, gender expression(s) and/or sexual orientation. Bigotry of any kind is not tolerated and is grounds for removal from the space.
We are a 21+ Venue, you must present a valid government-issued ID for entry.
No outside beverages or liquids are permitted in 2Bears Tavern Group bars at any time.
EMBRACE | CELEBRATE | EXPLORE

SMOOCH
The music is mighty, consent is hawt, and kissing is key at 💋 SMOOCH 💋 . Spend the evening sharing some of your liplockable lust with someone in a snog or three in our kissing booth. Plus, candy treats for all!
We've got two levels of music, a house vibe upstairs and a techno vibe downstairs, to inspire your particular mood, get you moving and make your move.
DJs
🔊 Compton Q
🔊 Club Chow
🔊 Madeline
🔊 Sorrbet
Hosts
💋 Princess
💋 Fantasy
💋 Secret Queen
Artist:
🖌️ Waldo Baez
Produced by Spiral Records
COVER:
Before 10pm: FREE
10pm-2am: $10
2am-Last call: $5
🌗 FRIDAY SPECIALS:
$5 Miller Lite Tallboys
$8 New Amsterdam & Red Bull
HOUSE RULES:
🔩 All bags/fanny packs/purses/etc. are subject to search
🔩 Gear encouraged, but not required
🔩 Clothes Check available
🔩 NO CAMERAS in The Hole
🔩 EVERYONE is welcome at Jackhammer regardless of color, size, body type, ability, gender expression(s) and/or sexual orientation. Bigotry of any kind is not tolerated and is grounds for removal from the space.
We are a 21+ Venue, you must present a valid government-issued ID for entry.
No outside beverages or liquids are permitted in 2Bears Tavern Group bars at any time.
EMBRACE | CELEBRATE | EXPLORE

STRAP'N
The Hole brings you the sexiest and most exhilarating jockstrap and jillstrap night in town with STRAP'N. Flaunt your hottest jock or jill straps, leaving little to the imagination! The Hole's infamous Pit opens up, inviting you to explore your deepest desires and indulge in the most exhilarating sensations. It's time to surrender to the thrill and let your inhibitions run wild!
We've got you uncovered with our FREE clothes check, so you can let go of inhibitions and fully immerse yourself in the electrifying atmosphere without any distractions.
Get STRAP’N and grab your sexiest jockstrap or jillstrap and join us for a night of unforgettable fun! **Dress code is not required but encouraged.**
🌗 THURSDAY SPECIALS
$3 House Shots
$5 New Amsterdam Cocktails
$5 Miller Lite Tallboys
HOUSE RULES
🔩 All bags/fanny packs/purses/etc. are subject to search
🔩 Gear encouraged, but not required
🔩 Clothes Check available
🔩 NO CAMERAS in The Hole
🔩 EVERYONE is welcome at Jackhammer regardless of color, size, body type, ability, gender expression(s) and/or sexual orientation. Bigotry of any kind is not tolerated and is grounds for removal from the space.
We are a 21+ Venue, you must present a valid government-issued ID for entry.
No outside beverages or liquids are permitted in 2Bears Tavern Group bars at any time.
EMBRACE | CELEBRATE | EXPLORE


Cruise
Dive into The Hole every Sunday from 9pm–4am for CRUISE, where you can flag a hanky or discover a new kink in a safe and discreet atmosphere. Keep those eyes peeled and those desires hard all night long.
🌗 SUNDAY SPECIALS
$5 Whiskeys, Ryes & Bourbons
HOUSE RULES
🔩 All bags/fanny packs/purses/etc. are subject to search
🔩 Gear encouraged, but not required
🔩 Clothes Check available
🔩 NO CAMERAS in The Hole
🔩 EVERYONE is welcome at Jackhammer regardless of color, size, body type, ability, gender expression(s) and/or sexual orientation. Bigotry of any kind is not tolerated and is grounds for removal from the space.
We are a 21+ Venue, you must present a valid government-issued ID for entry.
No outside beverages or liquids are permitted in 2Bears Tavern Group bars at any time.
EMBRACE | CELEBRATE | EXPLORE

BEARRACUDA CHICAGO: SWEATY JOCK PARTY
Bearracuda RETURNS to Jackhammer for our SWEATY JOCK PARTY! Flash your jock at the door for discounted admission! Two floors, basement cruising, Hot Go-Go's and hundreds of guys await you on Saturday, March 8th. Clothes check available! 9PM-LATE
Get into trouble in THE HOLE (Dress SEXY in The Hole) with REDUX (DJ CT & Wyser)
SATURDAY SPECIALS:
$3 House Shots
$5 Miller Lite Tallboys
HOUSE RULES:
🔩 All bags/fanny packs/purses/etc. are subject to search and MUST be checked into Coat Check
🔩 Gear encouraged, but not required
🔩 Clothes Check available
🔩 NO CAMERAS in The Hole
🔩 EVERYONE is welcome at Jackhammer regardless of color, size, body type, ability, gender expression(s) and/or sexual orientation. Bigotry of any kind is not tolerated and is grounds for removal from the space.

THE KENNEL
The pack is gathering—are you ready to run wild? Get lost in the beats, the energy, and the thrill of the night with an electrifying lineup of DJs and hosts.
🎶 Music by DJ Wolfy, PK FiRE, Ryan Cezanne and MDAcid
🐾 Hosted by Ronno, TRAMP, Pup Skyler, Pup Ion and Pup Puck
Let loose, dance hard, and embrace the night—The Kennel is waiting.
🔩 $5 Cover - Tickets can be purchased at the door
🔩 21+ Only
🌗 FRIDAY SPECIALS
$5 Miller Lite Tallboys
$8 New Amsterdam & Red Bull
HOUSE RULES:
🔩 All bags/fanny packs/purses/etc. are subject to search
🔩 Gear encouraged, but not required
🔩 Clothes Check available
🔩 NO CAMERAS in The Hole
🔩 EVERYONE is welcome at Jackhammer regardless of color, size, body type, ability, gender expression(s) and/or sexual orientation. Bigotry of any kind is not tolerated and is grounds for removal from the space.
We are a 21+ Venue, you must present a valid government-issued ID for entry.
No outside beverages or liquids are permitted in 2Bears Tavern Group bars at any time.
EMBRACE | CELEBRATE | EXPLORE


Cruise
Flag it. Find it. Cruise The Hole—Sunday nights from 9pm–4am. Grab your hanky and Cruise.
🌗 SUNDAY SPECIALS
$5 Whiskeys, Ryes & Bourbons
HOUSE RULES
🔩 All bags/fanny packs/purses/etc. are subject to search
🔩 Gear encouraged, but not required
🔩 Clothes Check available
🔩 NO CAMERAS in The Hole
🔩 EVERYONE is welcome at Jackhammer regardless of color, size, body type, ability, gender expression(s) and/or sexual orientation. Bigotry of any kind is not tolerated and is grounds for removal from the space.
We are a 21+ Venue, you must present a valid government-issued ID for entry.
No outside beverages or liquids are permitted in 2Bears Tavern Group bars at any time.
EMBRACE | CELEBRATE | EXPLORE

Belly Up
Join us on Sat, Mar 1st, starting at 9pm for a night of bringing together chubs, chasers, bears, gainers, encouragers, and admirers. Dance the night away with music from DJs Jesse Mercado, Robert Ratola and Mister Wallace in a fun, inclusive space that appreciates big bellies and chubby folks.
Big Bears, Beautiful Bellies, and their admirers—come together and enjoy! 🐻
COVER
Before 10pm: FREE
10pm-2am: $10
2am-Last call: $5
🌗 SATURDAY SPECIALS
$3 House Shots
$5 Miller Lite Tallboys
HOUSE RULES:
🔩 All bags/fanny packs/purses/etc. are subject to search and MUST be checked into Coat Check
🔩 Gear encouraged, but not required
🔩 Clothes Check available
🔩 NO CAMERAS in The Hole
🔩 EVERYONE is welcome at Jackhammer regardless of color, size, body type, ability, gender expression(s) and/or sexual orientation. Bigotry of any kind is not tolerated and is grounds for removal from the space.
🔩 No outside beverages or liquids are permitted in 2Bears Tavern Group bars at any time.

Fetish Friday: Bark After Dark
Unleash your inner canine at BARK AFTER DARK! This unique event brings together pup play enthusiasts for an evening of lighthearted discovery every fourth Friday of the month at Jackhammer. Embrace your inner trainer or puppy and join us for an unforgettable experience that will set your tail wagging and your heart racing.
🌗 ALL DAY & NIGHT SPECIALS
$5 Miller Lite Tallboys
$8 New Amsterdam & Red Bull
🔩 $5 Cover at Jackhammer at 10pm
🔩 Fetish Dress Code encouraged but NOT required
🔩 All bags/fanny packs/purses/etc. are subject to search and MUST be stored in a locker or checked
Fetish Friday is a weekly event from 9pm–4am that features rotating themes and parties. Participation in themes is totally optional and accessible to all—from newbies to the more experienced—and intended to encourage guests that are interested in the theme to explore and learn in a safe, LGBTQIA+ environment.
EMBRACE | CELEBRATE | EXPLORE

STRAP'N
The Hole brings you the sexiest and most exhilarating jockstrap and jillstrap night in town with STRAP'N. Flaunt your hottest jock or jill straps, leaving little to the imagination! The Hole's infamous Pit opens up, inviting you to explore your deepest desires and indulge in the most exhilarating sensations. It's time to surrender to the thrill and let your inhibitions run wild!
We've got you uncovered with our FREE clothes check, so you can let go of inhibitions and fully immerse yourself in the electrifying atmosphere without any distractions.
Get STRAP’N and grab your sexiest jockstrap or jillstrap and join us for a night of unforgettable fun! **Dress code is not required but encouraged.**


Cruise
Dive into The Hole every Sunday from 9pm–4am for CRUISE, where you can flag a hanky or discover a new kink in a safe and discreet atmosphere. Keep those eyes peeled and those desires hard all night long.
🔩 NO COVER | NO CODE
🔩 All bags/fanny packs/purses/etc. are subject to search and MUST be stored in a locker or checked
🌗 ALL DAY & NIGHT SPECIALS
$5 Whiskeys, Ryes & Bourbons

BUTCH PLEASE
Chicago’s premier queer, kink, and fetish house party is BACK and hotter than ever for a full bar takeover🔥! Join us for a night of pure queer magic, where beats are dirty, vibes are wild, and everyone is free to express their most fabulous, fierce, and kinky selves. 🖤✨
Get ready to break free and let your true self shine at Butch Please—the ultimate queer, kink, fetish, leather house music extravaganza! This is your invitation to a night where bold meets beat, and every twist of leather and flash of color celebrates YOU.
Dress Code: Unapologetically you—rock that leather, flaunt your favorite fetish gear, or come as you are in your most vibrant, fearless self! Expect pulsating house rhythms, a dance floor charged with electrifying energy, and a safe space for self-expression and exploration. Whether you're a seasoned veteran of the scene or just curious about diving into new realms, this night is all about celebrating diversity, passion, and pure, unfiltered fun.
COVER:
💄💋FREE ENTRY BEFORE 10 PM💋💄
⚡️$10 AFTER 10 PM⚡️
SATURDAY SPECIALS:
$3 House Shots
$5 Miller Lite Tallboys
HOUSE RULES:
🔩 All bags/fanny packs/purses/etc. are subject to search and MUST be checked
🔩 Gear not required but HIGHLY suggested!
🔩 Clothes Check available
🔩 NO CAMERAS in The Hole

Fetish Friday: Gear
GEAR up and get into Jackhammer for Fetish Friday: GEAR, every 3rd Friday of the month. GEAR is dedicated to showcasing your hoods, harness, leather and rubber (and everything in between). Whether you've got a collection or are trying out your first piece, GEAR is here to encourage you to embrace, celebrate and explore the scene.
🌗 ALL DAY & NIGHT SPECIALS
$5 Miller Lite Tallboys
$8 New Amsterdam & Red Bull
🔩 $5 Cover at Jackhammer at 10pm
🔩 Fetish Dress Code encouraged but NOT required
🔩 All bags/fanny packs/purses/etc. are subject to search and MUST be stored in a locker or checked
Fetish Friday is a weekly event from 9pm–4am that features rotating themes and parties. Participation in themes is totally optional and accessible to all—from newbies to the more experienced—and intended to encourage guests that are interested in the theme to explore and learn in a safe, LGBTQIA+ environment.
EMBRACE | CELEBRATE | EXPLORE


Cruise
Flag it. Find it. Cruise The Hole—Every Sunday night from 9pm–4am. Grab your hanky and Cruise.
🔩 NO COVER | NO CODE
🔩 All bags/fanny packs/purses/etc. are subject to search and MUST be stored in a locker or checked
🌗 ALL DAY & NIGHT SPECIALS
$5 Whiskeys, Ryes & Bourbons

FREAQ
🔥 Step into the shadows and turn up the heat—FREAQ returns to Jackhammer and The Hole on Saturday, Feb 15th, for a night of scandalous beats, tantalizing moves, and full-venue indulgence.
Slip into something scandalous or strip down to almost nothing—it’s your time to shine, seduce, and dominate the night. Let’s make this a FREAQ to remember. 🖤
DJs
🔊 Mister Hoochiemama
🔊 Ariel Zetina
🔊 Glamour Cadaver
Hosts
✨ Lilith Towers
✨ Charlie Calvin
✨ Hex Next
We'll also be launching our first OPEN DECKS for DJs from 7–10pm. Get some experience at the event and learn how to work our house! Open decks sets will be recorded and included as part of a FREAQ OPEN DECKS Soundcloud playlist. Signup is first come, first serve.
DJ Equipment Links:
🎛️ Pioneer CDJ-3000
🎚️ Pioneer DJM-900NXS
Produced by Spiral Records
No Cover before 10pm / $10 after
🌗 SATURDAY SPECIALS
$3 House Shots
$5 Miller Lite Tallboys
HOUSE RULES:
🔩 All bags/fanny packs/purses/etc. are subject to search and MUST be checked into Coat Check
🔩 Gear encouraged, but not required
🔩 Clothes Check available
🔩 NO CAMERAS in The Hole

SMOOCH
The music is mighty, consent is hawt, and kissing is key at 💋 SMOOCH 💋, Jackhammer's new dance party premiering on Valentine's Day Friday starting at 9pm! Don't let your V-Day be a bust when you could be sharing some of that lust with someone in a snog or three at SMOOCH! We've got two levels of music, a house vibe upstairs and a techno vibe downstairs, both to inspire your particular mood to make a move.
DJs
🔊 Club Chow @clubchow
🔊 Madeline @soft.content
🔊 Kiki Kuamo'o @kuamo.o
🔊 Robert Ratola @robertratola
Hosts
👅 Princess @thamidwestprincess
👅 Daniella Deluna @danielladeluna
📷 Daniella's Photo by Glen Gyssler @gyssler
Photo Art Direction by Daniella Deluna
👅 Ben Trotter @_trotterben
Artist:
🖌️ Waldo Baez @waldogarabato
U don't have 2 be cool 2 rule my world, ain't no particular sign I'm more compatible with, I just want ur extra time and ur💋.
Produced by Spiral Records
No Cover before 10pm / $10 after
🌗FRIDAY SPECIALS
$5 Miller Lite Tallboys
$8 New Amsterdam & Red Bull
HOUSE RULES:
🔩 All bags/fanny packs/purses/etc. are subject to search and MUST be checked into Coat Check
🔩 Gear encouraged, but not required
🔩 Clothes Check available
🔩 NO CAMERAS in The Hole
🔩 EVERYONE is welcome at Jackhammer and The Hole regardless of color, size, body type, ability, age (21+), gender expression(s) and/or sexual orientation. Bigotry of any kind is not tolerated and is grounds for removal from the space.