The Newport Peek-Easy
Apr
4
7:00 PM19:00

The Newport Peek-Easy

Catch some of Chicago's finest burlesque, belly dance, drag, and variety entertainers plus screenings of incredible digital content, played live in this hour-long show.

Specialty cocktails, intimate tables and a true speakeasy feel make this a memorable experience for date night, bachelorette parties, or a place to kick off your bar crawl - we're a block from both to Northalsted (formerly Boystown) and Wrigleyville! Within walking distance of the Addison Red Line, Belmont Brown Line, and off a Clark Street bus stop.

Bring your tipping dollars for an interactive night you'll never forget.

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Untitled Supper Club
Apr
23
8:00 PM20:00

Untitled Supper Club

We’re throwing it back to the roaring ’20s with our vintage, Prohibition Era-inspired design. Our sumptuous 18,000 square-foot restaurant, bar and live entertainment space hosts the largest selection of American whiskies in the world as well as carefully crafted cocktails. Our dining menu includes shareable bites, perfect pastas and beautifully creative desserts. While you dine and drink the night away, you can enjoy world-class entertainment with weekly music and titillating cabaret-style performances from Chicago’s finest. 

So what are you waiting for? Come join us for an undeniably unique and sensuous night out in the windy city.

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Sounds Like A Plan!
Mar
6
7:00 PM19:00

Sounds Like A Plan!

Calling all game show lovers, music nerds, and comedy fans! Sounds Like a Plan! is a live game show where a panel of local comedians, musicians, and Chicago theater royalty face off in hilarious music-themed games. PLUS! chances for audience members to play along with trivia and win local prizes! A hilarious game show featuring all things music, where comedians face off in devious challenges and YOU can compete for cute prizes!

Hosted by Plucky Rosenthal with Alex Tsarpalas

The March 6th panel features Casey Brown, Amy Sumpter, and The Sierra White!

For tickets and more information click here.

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Untitled Supper Club
Feb
12
8:00 PM20:00

Untitled Supper Club

We’re throwing it back to the roaring ’20s with our vintage, Prohibition Era-inspired design. Our sumptuous 18,000 square-foot restaurant, bar and live entertainment space hosts the largest selection of American whiskies in the world as well as carefully crafted cocktails. Our dining menu includes shareable bites, perfect pastas and beautifully creative desserts. While you dine and drink the night away, you can enjoy world-class entertainment with weekly music and titillating cabaret-style performances from Chicago’s finest. 

So what are you waiting for? Come join us for an undeniably unique and sensuous night out in the windy city.

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Fatlesque Fest 2026!
Jan
17
7:30 PM19:30

Fatlesque Fest 2026!

From the rhinestone studded mind behind “What the Funk?! An All BIPOC Burlesque Fest” and “Queer Prom Seattle”…Fatlesque Fest Northwest is on a mission to thicken up burlesque stages all over the country, starting with The Triple Door in Seattle, Washington. A three night festival—Sierra is proudly performing on night 3!

Click here for tickets and more information.

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