Male strippers, party butlers & cabana boys in Chicago
For Chicago bachelorettes, birthdays and girls' trips. We come to your Airbnb, hotel suite or pool, and you set how cheeky it gets.
Your Chicago hostPlanning a Chicago bachelorette party?
Chicago, the "City of Big Shoulders," is an unbeatable destination for throwing a massive birthday bash or an unforgettable bachelorette party. From the high-rise glamour of the Magnificent Mile to the vibrant nightlife of River North and West Loop, Chicago offers endless opportunities for a high-profile private party.
No matter what you're celebrating, having premium party entertainment ready to go is the key to a stress-free event. The Cheeky Butlers offers the ultimate in-house experience with highly professional and charming shirtless waiters and cabana boys who are ready to host naughty games and serve body shots. We also provide expert adult entertainment, including vetted exotic dancers and lap dance providers, ensuring your Chicago celebration is both classy and wild.
We serve groups traveling from all over the Midwest and beyond, including major metropolitan areas like Milwaukee, Indianapolis, Detroit, and St. Louis. Whether you're celebrating birthdays, baches, or whatever bespoke adventure it may be, Chicago has everything you need right on a silver platter.
Who we send to Chicago
Every one of these comes to you, anywhere in Chicago — your Airbnb, your hotel suite, your pool deck.
What we host in Chicago
Chicago gives you the rooftops, the river and the deep-dish nights. We handle the hours in between — getting ready, pre-drinks, games, the last hour before the cars arrive. That is the part most groups remember.
Best things to do on a Chicago bachelorette
Our favourite spots, nights out and experiences. Book your butler for the part of the weekend that happens at your place.
Clubs & unique dining experiences
Cool things to do
Our Chicago partners
Partying elsewhere in the Midwest and beyond?
Chicago party FAQs
Do you come to our Airbnb or hotel in Chicago?
Yes. Your butler comes to you: your Airbnb, rental, hotel suite or pool in Chicago and the surrounding area. If he has to travel more than about an hour, any travel fee is quoted and agreed before you pay.
How far ahead should we book our Chicago party?
Three days out is the realistic minimum if you want us to guarantee someone. For weekends and peak season, book as early as you can.
How cheeky can it get?
You have complete say. Tell us the level you want, mild or wild, and how much he wears, and we match you with an entertainer who is comfortable with it. Mild is a completely normal booking.
How many butlers do we need?
Under ten guests, one butler is usually plenty. Bigger than that, two makes more sense so nobody is waiting for a drink. More than two? Text us and we will put something together.
Are your entertainers vetted?
Yes. Every Cheeky Butler is vetted and professional. Our entertainers do not provide sexual services, and nobody touches an entertainer without his permission.
Ready to book your Chicago party?
Tell us the date and the vibe. We'll send back your guy, your package and the price.
Vetted & professional · We come to you · 500+ parties hostedPremium entertainment for parties, milestones, corporate events, and private functions. We are in 30+ cities across the USA.
Text to Book: (561) 690-7591
2026 © The Cheeky Butlers — All Rights Reserved. Operated by BDM Promotions.
Our Chicago Partners
The partners we trust for a Chicago bachelorette. Tap any partner to visit them, and mention CHEEKYBUTLER for 10% off.
Hibachi Guru
A private hibachi chef and a 90-minute live show, right at your Airbnb — dinner and a show, served. In 60+ cities.
Visit Hibachi Guru →