What you'll do:

Private 27 ft Sea Ray Charters for Day Parties & Playpen Cruises

Cruise Chicago’s lakefront aboard a private 27 ft Sea Ray designed for smaller groups looking to celebrate on the water. Whether you are planning a bachelor or bachelorette party, birthday outing, or casual summer hang, this charter offers the perfect mix of relaxation, music, and skyline views. Spend the day anchored at the Playpen, floating in the water, enjoying drinks with friends, and soaking up the sun while your captain handles the navigation.

Flexible Charter Options

Choose between 3-hour and 4-hour experiences depending on how long your group wants to stay on the water. The shorter option is perfect for quick celebrations and afternoon cruises, while the extended charter gives your group more time to swim, lounge, and enjoy Chicago’s iconic waterfront atmnmosphere.

Small Group Luxury Experience

The Sea Ray offers a more intimate boating experience for groups of up to 8 passengers. With comfortable seating, Bluetooth audio, and plenty of room to relax, it is ideal for groups looking for a private and laid-back day on Lake Michigan without the crowds of larger party boats.

Why we love it for your party:

• • Cooler Filled with Ice & Water: Keep your drinks cold and your group refreshed throughout the cruise.

  • Floating Water Mat & Noodles: Lounge and swim at the Playpen with included water accessories.

  • Bluetooth Sound System: Connect your playlist and enjoy your favorite music while cruising Chicago’s shoreline.

  • BYOB Friendly: Bring your favorite snacks and beverages onboard for a fully personalized experience.

About this experience partner:

Lakeshore Charter is a Chicago-based private boat charter company offering customized experiences on Lake Michigan for groups looking to celebrate, relax, and enjoy the city from the water. From Playpen day parties to skyline cruises and fireworks outings, their experienced captains and fully equipped boats make planning effortless for every group.

Additional information:

What to bring

• Swimwear & Towels: dip in the water off the swim platform and float pad.

• Sun Protection: Sunglasses, hats, and lotion sunscreen (please no spray-on sunblock, as it stains the deck).

• Footwear: Soft-sole shoes or flip-flops (we usually go barefoot on board).

• Food/Drinks: Feel free to bring snacks and your favorite drinks (please avoid red wine).

• The Vibe: Have your favorite playlist ready to pair with the speakers!