About this Experience
What you'll do:
Step aboard Wet Again Charters and get ready for an unforgettable time on the water!
Set Sail – Cruise Chicago’s waters in comfort and style.
Relax and Unwind – Lounge on deck, soak up the sun, and enjoy the views.
Celebrate – Perfect for birthdays, special occasions, or just because!
Enjoy Chicago’s #1 Boat Spot – “The Play Pen” – The "party" spot on the water
Have Fun in the Water – Option to jump in swim, play, relax and make every moment a memory.
With Wet Again Charters, it’s all about good vibes, great people, and amazing experiences on the lake.
Your adventure is our priority—every detail, every trip, every wave is designed for you to enjoy the ultimate charter experience.
Why we love it for your party:
Spacious, Luxury Vessel – Plenty of room for friends, dancing, and fun on the water.
High-Quality Sound System – Pump your favorite tunes and keep the party going.
The Play Pen Experience – Chicago’s top boat spot for swimming, splashing, and enjoying the water.
Unforgettable Views – Take in the stunning Chicago skyline while celebrating.
Fun and Relaxation Combined – Set sail, unwind, and make memories with friends.
About this experience partner:
Set sail on Wet Again Charters and enjoy the ultimate day on Chicago’s waters. Cruise past the skyline, soak up the sun, and unwind with friends on a spacious, luxury boat.
Dive into The Play Pen, Chicago’s top spot to swim, splash, and have a blast right from the boat. Lounge on deck, toast to celebrations, and make the most of every moment on the water.
With a powerful sound system, plenty of room to move, and epic lakefront views, it’s the perfect mix of fun, relaxation, and unforgettable memories. Whether it’s a birthday, bachelor party, or just a day to celebrate, this is the way to experience Chicago from the water.
Additional information:
Guests are welcome to bring snacks, drinks, and your favorite tunes.
Don’t forget your swimsuit and towel—jumping into The Play Pen is part of the fun!
Life jackets are provided for safety, but swimming and floating around is encouraged.
The boat is fully equipped with a sound system, plenty of seating, and space to dance or relax.
Book This Experience
Visit the experience booking site to check availability and book your experience.
LocationChicago, IL
3100 S DuSable Lake Shore Dr, Chicago, IL 60616, USAChicago, IL
Frequently Asked Questions
Does a captain come with the boat?
For our Bareboat Charters, a captain is hired separately by the Charterer. Captains typically charge $125–$175 per hour before gratuity, which is paid directly to your captain. Upon completion of booking you will receive a list of captains you may select from familiar with our vessel.
Can we play our own music through the speakers?
All of our vessels are equipped with premium, upgraded Bluetooth sound systems linked to an onboard Ipad equipped with Apple Music to enjoy while underway.
What time do I need to arrive for check-in?
We highly recommend using ride-sharing or car services due to limited and/or costly parking. Traffic around the harbors can be significant, especially on holidays or summer weekends. Plan to arrive at least 30 minutes prior to departure to allow ample time to walk from drop-off or parking to our dock, check in, get settled, and depart on time.
Can I bring my own food and drinks?
Guests are welcome to bring their own food and beverages, including alcohol. Boat will have cooler onboard for your use. Please avoid glass containers and staining liquids (such as red wine or cranberry juice) to prevent damage fees. For safety, stovetops are disconnected, and microwaves work only while docked and on shore power.
What are your operating hours and months?
We are open 7 days a week. Chicago’s boating season runs from late spring through early fall when conditions are ideal for being on the water, typically April to late October. Availability and peak times may vary depending on weather, special events, and seasonal demand.
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What should I wear?
Comfortable, weather-appropriate clothing is best for your boating experience. Light layers and sun protection like hats or sunglasses are recommended. Swimwear is perfect if you plan to take a dip, and for evening cruises, bring a light jacket as it can get cooler on the water. Please refrain from denim as it may dye the seats which can incur damage fees.
