Chicago's Premier Yacht Fleet.

With 20 iconic yachts to choose from, Knot My Boat Charters offers luxury and affordable options for unforgettable events on Lake Michigan. Whether you're cruising the river, enjoying fireworks, or spending a fun day at The Playpen, our fleet ensures the ultimate in comfort and entertainment.

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Chicago's Premier Yacht Fleet - 70ft Sea Ray cruising Lake Michigan

Lake Michigan, Chicago

20+ Yachts

Sport Cruisers to Luxury Yachts

37' to 72' Fleet Range

Lake Michigan

Chicago River & Harbors

Playpen Access

Premium Experience

Professional Captains

Full Service & Support

Browse Our 2026 Fleet - Private Yacht Rentals in Chicago

With our 13-passenger vessels departing from 31st Street Harbor and our 49-passenger vessels departing from Burnham Harbor, we offer unforgettable private outings designed for every occasion. Perfect for families, friends, small groups, or corporate outings, our charters are a great way to take in unmatched views of Chicago from the water. Whether you're gliding through the Chicago River or anchoring in The Playpen, every vessel offers a smooth and scenic escape. Looking for a worry-free day? All 49-passenger options include a licensed captain to elevate your experience, and for our 13-passenger vessels, captains are available to book at the end of checkout. Browse the full lineup below and find the perfect boat for your next adventure.

What to Know

Before You Explore Chicago's Top Yacht Options

14 to 49 passengers

Commercial Yacht Charters

Ideal for corporate events and large social gatherings, our commercial yacht charters accommodate between 14 and 49 passengers. Enjoy a spacious, luxurious setting perfect for networking, celebrations, or special occasions on the water.

1 to 13 passengers

Bareboat Yacht Charters

For a private and flexible experience, our bareboat yacht charters hold up to 13 passengers. Cruise at your own pace, whether for a relaxing day, a celebration, or a scenic escape.