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Skirt Social | Cocktails
Chicago
Thursday, May 21st, 2026
Chicago
Thursday, May 21st, 2026
A little flirtation over beautifully crafted cocktails? Absolutely.
Join us this spring for a sexy, laid-back Skirt Social night out at one of Chicago’s most beloved queer cocktail bars. This is your invitation to connect, flirt, and mingle with fellow curious members between our more intimate soirées.
Whether you’re a longtime Skirt member or brand new to the community, this evening offers the perfect vibe for meeting like-minded souls in a warm, stylish space that celebrates inclusivity, chemistry, and the art of conversation.
Come as you are. Stay as long as you like. Let the night unfold.
Entertainment
Join Skirt Club for cocktails and connection at Dorothy Downstairs — Chicago’s iconic LGBTQ cocktail bar tucked beneath the city, where intimacy lingers, conversation flows easily, and every drink feels like a quiet invitation.
As the evening unfolds, the lights glow low and the room fills with possibility. This is your moment to flirt, connect, and lean into that unmistakable Skirt Club spark.
Entry
Tickets from $25
Your ticket unlocks our reserved space at one of Chicago’s most beloved lounges — where conversations flow easily, glances linger, and each crafted cocktail becomes a reason to stay a little longer.
"Bring a Bestie" Tickets from $50
Enjoy...
"Bring a Bestie" Tickets from $50
Enjoy...
- All of the above mentioned plus the opportunity to share this experience with a friend.
Please note: this event is exclusive to women. No male guests are permitted. We request that non-members remain respectful to the privacy of our members’ identities, and will be asked to ‘sign in’ with their name and email address upon arrival.
20% Discount for Enchantress members
Upgrade your membership to gain premium access
Upgrade your membership to gain premium access
Location
Timings
Reservation from 7pm... until 10pm
Add to calendar
Dress Code
Night Temptress
Check out our Pinterest page for more inspiration HERE
Dress to impress... wear something that seduces your own reflection, Darling. Think a sexy LBD or something smokin' you'd wear on a hot date!
Check out our Pinterest page for more inspiration HERE
Dress to impress... wear something that seduces your own reflection, Darling. Think a sexy LBD or something smokin' you'd wear on a hot date!
The Skirt Club Experience
WHAT IS A SKIRT SOCIAL?
Our smaller group gatherings are designed to keep the community engaged and curious. Think smart, professional women looking to meet with like-minded local ladies. Perfect for staying connected between our larger Events and Signature Play Parties. Our about and FAQ pages will give you further context.
Our smaller group gatherings are designed to keep the community engaged and curious. Think smart, professional women looking to meet with like-minded local ladies. Perfect for staying connected between our larger Events and Signature Play Parties. Our about and FAQ pages will give you further context.
Notes
Skirt Club parties are for members only.
Tickets are non-refundable and non-transferable.
No longer able to join us? Cancel your ticket via your profile.
Seductress members can cancel to credit up to 7 days before the event.
Enchantress members can cancel to credit up to 48 hours.
Temptress members have no cancellation option.
Upgrade your membership to gain premium access.
Seductress members can cancel to credit up to 7 days before the event.
Enchantress members can cancel to credit up to 48 hours.
Temptress members have no cancellation option.
Upgrade your membership to gain premium access.
Strictly no photography allowed.
Tickets are strictly non-refundable and non-transferable. Please see our Etiquette Guide and Event Policy prior to purchasing a ticket.