Discover the stunning Chicago skyline from Lake Michigan on a private boat tour with Main Deck Enchantment. Enjoy personalized service, breathtaking views, and an exclusive water adventure designed for your groups.
More ways to explore the area's outdoor wonders
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Difficulty
easy
Duration
2–3 hours
Fitness Level
Suitable for most guests, minimal physical activity required
Wildlife
History
Chicago’s waterfront has been central to the city’s development from a busy shipping port to a vibrant recreational area since the 1800s.
Conservation
Efforts are ongoing to preserve Lake Michigan’s water quality and promote eco-friendly boating practices within the area.
Island Party Boat
Discover the stunning Chicago skyline from Lake Michigan on a private boat tour with Main Deck Enchantment. Enjoy personalized service, breathtaking views, and an exclusive water adventure designed for your groups.
Island Party Boat is a Chicago-based boat operator offering tiki-themed cruises, skyline charters, and private yacht rentals on Lake Michigan and the Chicago River. The company operates a range of vessels from 24‑foot center consoles to an 80‑foot tiki‑chic yacht, accommodating intimate six-passenger charters and large groups up to 120 guests.
Trips include themed public cruises such as the Chicago River Tiki Bar Cruise and Sunday Mimosa n' Bloody Mary Cruises, plus private charter options like Upper Deck Enchantment, Main Deck Enchantment, and Island Time. Many experiences depart from the Chicago Riverwalk and provide skyline views, island-style decor, and tropical cocktails from full or open bars.
Onboard amenities vary by vessel and specific trip but commonly feature Bluetooth sound systems, multiple decks, restroom access, and covered areas for comfort. Select yachts include an Admiral’s Lounge and upscale spirits; smaller boats offer compact, private cruises with complimentary beverages or included drink credit. One vessel includes a water slide for added entertainment.
Island Party Boat markets a variety of durations, from shorter 75–90 minute skyline and river cruises to extended three-hour private charters. The operator serves tourists and local groups seeking a festive, island-inspired experience on the water. All trip descriptions specify capacities, deck configurations, and some beverage inclusions, allowing groups to choose the appropriate vessel and service level for events, celebrations, or sightseeing along Chicago’s river and lakefront. Booking details, exact departure points, and onboard policies are provided per trip listing so groups can plan with clear expectations and flexible options.
Vessel Sizes
24–80 ft
Multiple boats for different groups
Max Capacity
120
Largest private charter capacity
Departure
Chicago Riverwalk
Dock location for many cruises
Tours Offered
10
Diverse river and lake experiences
Reserve a terrace-style deck, private yacht, or intimate center-console charter for skyline views, tropical cocktails, and memorable group events.
Arrive early for the best viewing spots
Getting to the dock ahead of your scheduled departure allows for a stress-free boarding process and some time to enjoy the city views.
Bring layers for changing weather
Weather on Lake Michigan can vary, so packing layers ensures you'll stay comfortable whether it's sunny or breezy.
Capture photos from multiple angles
Use the boat's different vantage points to capture diverse shots of Chicago’s skyline and waterfront scenery.
Secure belongings during the cruise
Hold onto essentials or store valuables safely to prevent losing them overboard while enjoying the tour.
Sunscreen
Protects your skin from sun exposure during daytime cruises on Lake Michigan.
summer
Hat or cap
Provides shade and shields your face from direct sunlight.
summer
Light jacket or windbreaker
Keeps you warm against cool breezes on open decks during cooler months.
spring|fall|winter
Camera or smartphone with extra battery
Ideal for capturing scenic views and memorable moments onboard.