
July 12, 2025
Boat Safety, Boating
Experience the magic of night boating in the Chicago Playpen, where the city skyline glimmers against the dark waters and the excitement of Navy Pier fireworks lights up the sky. Whether you're planning a romantic evening or a family adventure, preparation is key to ensuring a safe and unforgettable outing. From mastering navigation tools to understanding the unique challenges of nighttime waters, this comprehensive guide will equip you with essential safety tips and insights. Dive into the thrill of the Playpen at night and discover how to make the most of this iconic summer experience!
“Whether it’s a romantic evening or a family adventure, the Playpen at night rewards the cautious. “
The Chicago Playpen, that iconic stretch of Lake Michigan just off the city’s stunning skyline, is a boater’s paradise. By day, it’s a vibrant hub for swimming, socializing, and soaking up the sun amid anchored yachts and speedboats. But as dusk falls, the Playpen transforms into a magical realm where the city’s lights dance on the water, and the air buzzes with anticipation for one of Chicago’s most beloved traditions: the Navy Pier fireworks.

Explore the waters by day first, know your tools inside out, and respect the lake's power.




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🚤 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
🚤 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! ✨
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
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! ☁️
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! 🎥
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! 🎥 ...
Pasta and great company? Immediately yes. We’re bringing together Chicago’s most talented to chat, dine, drink, and get creative together ✨
Pasta and great company? Immediately yes. We’re bringing together Chicago’s most talented to chat, dine, drink, and get creative together ✨ ...
We`re riding out summer until September 22nd and beyond 🛥️
We`re riding out summer until September 22nd and beyond 🛥️ ...
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 🎟️
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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