The Playpen® Chicago

Tripling the “Yacht Tax”: What Mayor Johnson Is Proposing and Why It Matters

Tripling the “Yacht Tax”: What Mayor Johnson Is Proposing and Why It Matters

In October 2025, Mayor Brandon Johnson proposed a bold plan to triple Chicago's "yacht…

Is the Playpen really a floating circus of pole dancers and steamy rendezvous?

Is the Playpen really a floating circus of pole dancers and steamy rendezvous?

Is the Playpen really a floating circus of pole dancers and steamy rendezvous? While…

Discover the Thrills of Chicago’s Playpen: Boating Community, Apps, and Glow Events

Discover the Thrills of Chicago’s Playpen: Boating Community, Apps, and Glow Events

Chicago’s Playpen is the ultimate summer playground on Lake Michigan, where influencers, families, and…

Sailing into Legend: The Thrilling Chicago Yacht Club Race to Mackinac

Sailing into Legend: The Thrilling Chicago Yacht Club Race to Mackinac

Sailing into Legend: The Thrilling Chicago Yacht Club Race to Mackinac is more than…

Chicago’s Proposed Mandatory Life Vest Law: Balancing Safety and Freedom on the Waves

Chicago’s Proposed Mandatory Life Vest Law: Balancing Safety and Freedom on the Waves

Chicago Alderman Stephanie Coleman has introduced a groundbreaking ordinance that mandates all boaters wear…

Discover the New Navy Pier Marina: Your Hub for Boating Adventures in Chicago

Discover the New Navy Pier Marina: Your Hub for Boating Adventures in Chicago

Discover the New Navy Pier Marina: Your Hub for Boating Adventures in Chicago Home…

Ultimate Guide to a Luxury Yacht Outing at Playpen Chicago: What to Bring, Wear, and How to Stay Safe While Having Fun

Ultimate Guide to a Luxury Yacht Outing at Playpen Chicago: What to Bring, Wear, and How to Stay Safe While Having Fun

Ultimate Guide to a Luxury Yacht Outing at Playpen Chicago: What to Bring, Wear,…

Night Boating in the Chicago Playpen: Essential Safety Tips and Fireworks Spectacle

Night Boating in the Chicago Playpen: Essential Safety Tips and Fireworks Spectacle

Experience the magic of night boating in the Chicago Playpen, where the city skyline…

How to Dock Your Boat at a Chicago Harbor and Anchor Safely at The Playpen

How to Dock Your Boat at a Chicago Harbor and Anchor Safely at The Playpen

Mastering how to dock your boat at a Chicago harbor and anchor safely at…

Before You Head Out to the Playpen in Chicago — 10 Yacht-Day Musts

Before You Head Out to the Playpen in Chicago — 10 Yacht-Day Musts

Fuel, pump-out, provisioning, weather gear, safety checks & permits—everything a Chicago Playpen boat rental…

Set Sail the Right Way: A Complete Playpen Chicago Guide for Renters & New Yacht Owners

Set Sail the Right Way: A Complete Playpen Chicago Guide for Renters & New Yacht Owners

Whether you’re a first-time renter or the proud owner of a shiny new cruiser,…

Spotting Illegal Charters in Chicago’s Playpen: A 2025 Boater’s Guide

Spotting Illegal Charters in Chicago’s Playpen: A 2025 Boater’s Guide

Spotting Illegal Charters in Chicago’s Playpen: A 2025 Boater’s Guide Home Blog June 15,…

The Playpen Chicago Captain Network: Your Path to Earning Income on Lake Michigan as a USCG-Licensed Captain

The Playpen Chicago Captain Network: Your Path to Earning Income on Lake Michigan as a USCG-Licensed Captain

If you’re a United States Coast Guard (USCG)-licensed captain looking to turn your maritime…

Navigating the Waves: A Comprehensive Look at the Chicago Boat Show January 8-12, 2025

Navigating the Waves: A Comprehensive Look at the Chicago Boat Show January 8-12, 2025

Navigating the Waves: A Comprehensive Look at the Chicago Boat Show January 8-12, 2025…

Exploring the Chicago Harbor Lock: History, Functionality, and Its Impact on Waterway Travel

Exploring the Chicago Harbor Lock: History, Functionality, and Its Impact on Waterway Travel

Exploring the Chicago Harbor Lock: History, Functionality, and Its Impact on Waterway Travel Home…

Chicago Celebrities Waterskiing at the Playpen—Yes, Even on Christmas Day!

Chicago Celebrities Waterskiing at the Playpen—Yes, Even on Christmas Day!

Chicago Celebrities Waterskiing at the Playpen—Yes, Even on Christmas Day! Home Blog December 26,…

Exploring the Boating Scene in Chicago: Harbors, Yachts, Charters, and More

Exploring the Boating Scene in Chicago: Harbors, Yachts, Charters, and More

Exploring the Boating Scene in Chicago: Harbors, Yachts, Charters, and More Home Blog December…

Where Is the Playpen Chicago and What Is It? A Complete Guide to the Windy City’s Unique Boating Hotspot

Where Is the Playpen Chicago and What Is It? A Complete Guide to the Windy City’s Unique Boating Hotspot

Where Is the Playpen Chicago and What Is It? A Complete Guide to the…

Discovering Chicago’s Harbors for the Ultimate Yacht Charter Experience

Discovering Chicago’s Harbors for the Ultimate Yacht Charter Experience

Discovering Chicago’s Harbors for the Ultimate Yacht Charter Experience Home Blog December 14, 2024…

The Playpen in Chicago: Its History, Features, Boating Scene, and Controversy

The Playpen in Chicago: Its History, Features, Boating Scene, and Controversy

The Playpen in Chicago: A Comprehensive Look at Its History, Features, Boating Scene, and…

About Us

Playpen Chicago is the official social network for entertainment in Chicago on and off the lake. Download the app and create your free profile to get invited to private yacht parties, meet yacht owners, and attend exclusive events

Join Playpen Chicago

Join Playpen Chicago

Create Your Free Profile Today and Find Your Friend With A Boat
🚤 Chicago’s Yacht Tax TRIPLE THREAT ⚓
Mayor Brandon Johnson’s 2026 budget aims to triple the city’s 7 % boat-mooring tax—raising it to 23.25 %.

The proposal targets high-end leisure craft to help fill a billion-dollar budget gap, but critics warn it could sink the city’s boating economy.

Would this make Chicago’s harbors less attractive—or is it a fair share for luxury boaters?
👇
Read the full breakdown in our featured article (link in bio)

#PlaypenChicago #ChicagoBoating #LakeMichiganLife #ChicagoPolitics #YachtTax #ChicagoHarbor #BoatLifeChicago #PlaypenScene #LuxuryLifestyle #WindyCityWaterfront

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We’re celebrating the end of the season on the water today with oysters by @loganoystersocials and bubbly thanks to @themetropolitanchicago!

While boating season may be coming to a close, we’re keeping things rolling all winter long. Keep an eye out for our events on land through next May! ✨

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When the city is your Playpen, the seasons become irrelevant—from the lake to downtown, we’re doing it all! ✨

Pasta and Chill: Pasta Making Class with @chefandysuarez 
Photography by @caseyalexandramedia 
Vibes by @playpenchicago

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Boating season is about to end but the fun doesn’t have to! Being a member of The Metropolitan, which has 50+ years of heritage as Chicago’s premier private club, means you get to enjoy all of these perks over the winter and more:

 ▪️Access Playpen Chicago x The Metropolitan events all year round and rotating 5–8 member-only events per week, from networking socials to themed dinners
▪️Located up above the city in the Willis Tower with panoramic skyline views
▪️Exclusive access to over 250 reciprocal clubs worldwide
▪️Coworking spaces perfect for remote professionals or creative entrepreneurs
▪️Family-friendly programming for when you want to mix business with personal life

Join us in the sky! ☁️

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Summer 2025 stole our hearts! Huge shoutout to @citywineryriverwalk for the vino, @chicagowinesnob for the wine wisdom, @caviardreamofficial and @nautichicago, @lifestyleboatrental for an epic Wine and Caviar bash at @navypierchicago ✨ Special thanks to @rockroseproductions for bringing the visual magic! 🎥

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Pasta and great company? Immediately yes. We’re bringing together Chicago’s most talented to chat, dine, drink, and get creative together ✨

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We're riding out summer until September 22nd and beyond 🛥️

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Summer’s not done until we say it is. Chicago, join us as we close the summer at Vice Yacht Club, Sept 19 with @thankyoufordancing 🪩

Tickets are limited! DM us with your Playpen Chicago username (it’s free to create an account on our app!) for a 25% off ticket promo code 🎟️

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