Playpen Chicago Events

Our events

Playpen Chicago Events

Daytime Boat Parties

@PLAYPENCHICAGO

Exclusive Outings

@PLAYPENCHICAGO

Yacht Soirees

@PLAYPENCHICAGO

Penthouse Parties

@PLAYPENCHICAGO

Why Choose us

We Are The Playpen - Join Today

Playpen Chicago hosts spectacular events with its partners in the boating, culinary and entertainment fields.

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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9/20 Saturday night fireworks at 9:30pm. DM for your boat or yacht. 
#boatsafechicago #boatersafety #viral #fyp #explore #labubu

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POV: That feeling when the city just clicks with your soul — the skyline, the food, the lake breeze — you just get it.

Things to do:
• Drop a ♥️ if Chicago is your vibe too
• Save this reel for your next city trip
• Share with a friend who needs to experience Chicago
• Go catch a sunset at the lakefront this week
• Romanticize your next city stroll

❤️ Like if Chicago is YOUR vibe
📌 Save this for inspo
📤 Share with your Chicago crew
📩 DM for collabs

About:
Chicago isn’t just a place — it’s a feeling. The perfect mix of big-city energy and Midwest warmth makes it unlike anywhere else. Whether it’s the lakefront at golden hour, deep-dish cravings, or late-night downtown adventures, Chicago vibes just hit different.

[chicago vibes aesthetic, windy city moments, chicago lifestyle reel, midwest magic, chicago downtown]
#ChicagoVibes #IfYouKnowYouKnow #WindyCityLove #MidwestCharm #CityAesthetic #POVReel #ExploreChicago #GoldenHourGlow #SkylineMagic #BigCityEnergy #WeekendInChicago #ViralReel #UrbanVibes
#Chicago #illinois #usa #america #visualsodyssey

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🌞 September isn’t slowing down! With gorgeous weather in the 80s and the lowest rates of the season, it’s the perfect time to get out on the water. Don’t miss your chance to book a yacht day while summer’s still shining—message us to reserve your spot! 🛥️✨

#yachtschicago #yachtlife #playpenchicago #chicago #lakemichigan #chicagoyachts #SummertimeChi #ChicagoEvents #luxuryyachtcharter

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9/14/25 - Happy Sunday and Bears Vs. Lions Game!

I am always happy to accept some foods

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Why is Chicago always a good time? 🌶️
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#foryoupage #explorepage #fyp #music #musicfestival #explore #vlog #blog #chicago #chicagoviews

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Soaking in the last days of summer. #chicago #playpen #labsofinstagram #rhoback

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The beauty of Chicago is best admired with a glass in hand.

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9/13/25 - Happy Saturday! Chicago cant make up its mind temperature-wise

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🌞 Don't Let Summer Slip Away!⚓️ September in Chicago brings sunny days, warm breezes, and unbeatable charter deals🛥️. It’s the perfect time to take in those stunning skyline views and enjoy the waters before the season ends! ⏳

Book now and create unforgettable memories. Use the link in our bio to reserve now or call/text us at 312-971-0334.
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#ChicagoBoatRental #LakeMichiganViews #BoatDayVibes #boatday #BoatLife #FriendsOnTheWater #SummerVibes #BoatRentalFun #endofsummer 
#BoatGoals #ChicagoSummer #OutOnTheWater #BookYourBoat
#WomenOwnedBusiness #ChicagoByWater #BoatDayChicago #ExploreChicago #LakeMichiganViews #ChiSummerVibes #noboatnofun #summertimechi #thingstodoinchicago
#chicagobucketlist #lakemichigan #blackownedbusiness

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Why Choose us

Playpen Chicago hosts spectacular events with its partners in the boating, culinary and entertainment fields.

Let's Go Out

The Best Days Are Spent On The Water

Join Playpen Chicago and find your friend with a boat.

Had the best time, excellent people, can’t wait to get back next summer!!

John Hess Google Review

Love playpen! Its allowed me to meet so many people and friends with boats and made Chicago more fun than I can imagine!

Maleah Allan Influencer