Chicago Skyline Cruise
A Chicago skyline boat tour with me is a relaxed, hospitality-focused way to experience the city from its most stunning vantage point—the water. Cruising along Lake Michigan, you and your guests enjoy unobstructed views of the downtown skyline, iconic landmarks, and the city’s world-famous architecture, all from the comfort of a private boat or yacht.
I offer multiple boats and yachts to choose from, making it easy to match the right vessel to your group size, style, and occasion. Whether you’re planning a casual sightseeing cruise, a romantic sunset tour, or an upscale private outing for your corporate event or wedding, I help tailor the experience to feel effortless and personal.
To elevate your skyline tour, I can handle the details for you—from picking up your provisions to arranging catering, drinks, and onboard entertainment through my trusted preferred vendor network. As a seasoned private event professional in Chicago, I work with some of the city’s top caterers, entertainers, and service partners to ensure everything flows seamlessly.
From the moment you step aboard, your only job is to relax and enjoy the view. A Chicago skyline tour with me is private, fully customized, and designed to showcase the city in its most unforgettable light.
Choose Your Boat
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Luxury Yacht
$825-1,200/hr range which includes captain & crew fees. Hosts up to 12 guests plus yourself.
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Mid Sized
$425/hr range which includes captain costs. Hosts up to 12 guests plus yourself.
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Large Group Charters
This catamaran is can hold up to 44 people and price depends on guest count.
Let’s Plan Your Trip!
Reserve Your Yacht
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Choose your preferred yacht, date, and timeframe. Once reserved, your vessel is secured and officially yours for the day. Think of this as placing the foundation for an unforgettable experience on Lake Michigan.
Connect With Your Captain
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Next, you’ll speak directly with Captain Scott to personalize the experience—route, anchor spots, timing, and onboard preferences. This is where your day takes shape, tailored to your style, your guests, and the vibe you’re after.
Arrive with your Cruise Crew
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On the day of your charter, simply arrive at the dock and step aboard. Your yacht is prepared, your captain is ready, and all that’s left to do is relax, enjoy, and let the lake do the rest.