Nothing beats a Chicago summer on a yacht — champagne on the deck, the skyline rolling by, and Lake Michigan stretching to the horizon. From intimate sunset sails to full-deck corporate events, yacht charters are the ultimate Chicago boating experience. Use the guides and bookable listings on this page to compare vessels, crew options, and price points.
Birthdays, anniversaries, and milestone moments
Impress clients with a private yacht experience
Golden-hour skyline views from the water
Yachts accommodating 20–100+ guests
Private yacht and sailboat charter options you can book online. These are instant-booking alternatives — not the only way to charter. For more private yacht charter options, browse related rental and charter category pages. Dining cruises are ticketed shared experiences, not private yachts.
Private charter
Bookable experience · Viator
Instant-booking private yacht charter on Viator. Browse related yacht and charter category pages for more private charter options you can book online.
Check availability & price
View Private Yacht Charter →
Private charter
Bookable experience · Viator
Private sailboat charter with captain near Navy Pier. Instant-booking alternative — browse related sailing and charter category pages for more options.
Check availability & price
View Private Sailboat Charter →
Shared ticketed cruise · Lake Michigan
Bookable experience · GetYourGuide
Golden-hour Lake Michigan skyline cruise — a classic Chicago evening on the water.
Check availability & price
See Cruise Times →
Shared ticketed cruise · Chicago River
Bookable experience · GetYourGuide
Brunch, lunch, or dinner on a Chicago River cruise with downtown architecture as the backdrop.
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See Tickets & Times →Boating Chicago may earn a commission when you book or shop through links on this page, at no additional cost to you. Learn more.
We're onboarding Chicago boating partners. Browse ticketed experiences above, or explore related category pages for rentals and charters.
List your boating business →Conditions, destinations, and guides that pair with this page.
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