The Playpen Chicago™

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…

The Playpen Chicago featured on Chicago’s Own WGN TV

The Playpen Chicago featured on Chicago’s Own WGN TV

The Playpen Chicago featured on Chicago’s Own WGN TV Home Blog December 10, 2024…

Spectacular Drone Show and Winter Festivities at Navy Pier

Spectacular Drone Show and Winter Festivities at Navy Pier

Spectacular Drone Show and Winter Festivities at Navy Pier Home Blog December 9, 2024…

Maximizing Fun, Minimizing Risk: Understanding Passenger vs. Crew Limits on Bareboat Charters in Chicago’s Playpen

Maximizing Fun, Minimizing Risk: Understanding Passenger vs. Crew Limits on Bareboat Charters in Chicago’s Playpen

Maximizing Fun, Minimizing Risk: Understanding Passenger vs. Crew Limits on Bareboat Charters in Chicago’s…

Is It Safe to Jump Off a Boat, Swim, or Use a Lily Pad at the Playpen in Chicago? A Comprehensive Guide

Is It Safe to Jump Off a Boat, Swim, or Use a Lily Pad at the Playpen in Chicago? A Comprehensive Guide

What are the factors that influence safety at the Playpen, including water conditions, weather,…

How to Find and Hire a Captain for Your Boat Charter at the Playpen in Chicago on Lake Michigan

How to Find and Hire a Captain for Your Boat Charter at the Playpen in Chicago on Lake Michigan

We’ll break down what a bareboat charter is, why captains are hired separately, how…

How to Charter a Boat at the Playpen in Chicago on Lake Michigan: A Complete Guide

How to Charter a Boat at the Playpen in Chicago on Lake Michigan: A Complete Guide

From choosing the right charter company and budgeting tips to what to bring 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
Persistence is key—follow us and download the Playpen Chicago app to find your friend with a boat in the Playpen!#chicago #playpen #lakemichigan #playpenchicago #summer2025 #theplaypenchicago #chicagonightlife

Persistence is key—follow us and download the Playpen Chicago app to find your friend with a boat in the Playpen!

#chicago #playpen #lakemichigan #playpenchicago #summer2025 #theplaypenchicago #chicagonightlife
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Your favorite app for all things Chicago boating, entertainment, and lake-life is right here ✨ follow and download the app to make your Chicago summer worth the winter wait 📲#Chicago #theplaypenchicago #summer2025 #playpenchicago #lakemichigan #playpen #chicagonightlife

Your favorite app for all things Chicago boating, entertainment, and lake-life is right here ✨ follow and download the app to make your Chicago summer worth the winter wait 📲

#Chicago #theplaypenchicago #summer2025 #playpenchicago #lakemichigan #playpen #chicagonightlife
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Is Chicago ready for this kind of spotlight?The Bear can move over—The White Lotus is about to put Chicago on the map! ✨

Is Chicago ready for this kind of spotlight?

The Bear can move over—The White Lotus is about to put Chicago on the map! ✨
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Huge news for Chicago ⚠️ Are you caught up on all of the seasons so far?Move over The Bear—The White Lotus is putting Chicago on the map! 🎥

Huge news for Chicago ⚠️ Are you caught up on all of the seasons so far?

Move over The Bear—The White Lotus is putting Chicago on the map! 🎥
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Catch a Chicago sunset on a yacht 🏙️ follow us for more lake content! Lake Michigan never looks better than from this vantage point. Get ready to book your private yacht charter through Playpen Chicago!

Catch a Chicago sunset on a yacht 🏙️ follow us for more lake content! Lake Michigan never looks better than from this vantage point. Get ready to book your private yacht charter through Playpen Chicago! ...

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The math isn’t mathing 🤔 follow for yacht event updates and to find your friend with a boat!Playpen Chicago’s got your yacht needs covered—find your captain and charter through our app.

The math isn’t mathing 🤔 follow for yacht event updates and to find your friend with a boat!

Playpen Chicago’s got your yacht needs covered—find your captain and charter through our app.
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Chicago has too much to offer to be sad 🙌 follow for updates on our events and to be a part of them!Are you a Chicago-based business and want to work together on Playpen Chicago’s next curated event?Create a free profile on our app (Playpen Chicago), list your service on our marketplace, and DM us your collaboration ideas to start a chat!🎥: @wallylaflair

Chicago has too much to offer to be sad 🙌 follow for updates on our events and to be a part of them!

Are you a Chicago-based business and want to work together on Playpen Chicago’s next curated event?

Create a free profile on our app (Playpen Chicago), list your service on our marketplace, and DM us your collaboration ideas to start a chat!

🎥: @wallylaflair
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Club Lake Michigan is about to be in full effect 🙌 follow for updates from the lake!

Club Lake Michigan is about to be in full effect 🙌 follow for updates from the lake! ...

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