A Grand Way to Cruise Chicago
If you’re looking to take your time on the water to the next level, our yacht rentals are the perfect way to do it. Whether you’re celebrating a wedding, hosting a corporate outing, or just planning a memorable day with friends, our yachts offer an unforgettable mix of luxury and fun. Available during our main season (April through November), these boats are designed for those moments when you want something a little more special.

Meet the Fleet

 

  B.O.R. — Sleek & Social

At 52 feet, B.O.R. is a renovated Cruisers Yachts 500 Express that’s built for entertaining. With an open cockpit made for mingling and a spacious foredeck perfect for sunbathing, this boat is a favorite for bachelor and bachelorette parties, client outings, and celebrations of all kinds.

• Capacity: Charterer + up to 12 guests
• Minimum Rental: 3 hours
• Best For: Parties, celebrations, and days at the Play Pen

 

 

 

Pathfinder — Classic & Sophisticated

If you’re looking for timeless elegance, Pathfinder delivers. This fully restored 63-foot Chris Craft yacht is a Chicago icon, offering a chic backdrop for intimate weddings, rehearsal dinners, milestone birthdays, or upscale business outings. Cruise the Chicago River, head out to Lake Michigan, or enjoy a chef-prepared meal on deck — no matter the occasion, Pathfinder makes it unforgettable.

• Capacity: Charterer + up to 12 guests
• Rental Window: 2–8 hours
• Best For: Weddings, milestone events, and elevated experiences

 

 

 

 

 

The Experience
Both yachts are captained vessels, so you can sit back and relax while a licensed professional handles the cruising. Want to make the day even more memorable? Guests are welcome to bring their own food, but we also offer the option of adding a private chef for a fully curated dining experience (just be sure to book three days ahead).

Before You Cruise
Arrive 30 minutes early for check-in.
Be sure the cardholder has signed the waiver and brings the booking card and ID.
Pick-up and drop-off are at Monroe Harbor, though other locations are available for an additional fee.

Ready to Book?
From social parties to once-in-a-lifetime events, our yacht rentals are a one-of-a-kind way to experience Chicago from the water. Whether you’re drawn to the sleek energy of B.O.R. or the timeless charm of Pathfinder, you’ll find the perfect setting for your celebration.

Get ready to relax, take in the views, and cruise Chicago in style.