Discover Chicago from a new angle with the Upper Deck Enchantment boat tour. This private experience offers stunning skyline views, personalized service, and a luxurious way to enjoy Lake Michigan. Perfect for special occasions or a unique outdoor adventure in the Windy City!
More ways to explore the area's outdoor wonders
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Difficulty
easy
Duration
2–3 hours
Fitness Level
Suitable for most fitness levels; minimal physical effort required
Wildlife
History
Chicago’s waterfront has been central to the city’s development, originally serving as a hub for shipping and trade in the Great Lakes region.
Conservation
The area actively promotes eco-friendly boating practices to protect Lake Michigan’s water quality and local wildlife habitats.
Island Party Boat
Discover Chicago from a new angle with the Upper Deck Enchantment boat tour. This private experience offers stunning skyline views, personalized service, and a luxurious way to enjoy Lake Michigan. Perfect for special occasions or a unique outdoor adventure in the Windy City!
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 seating
Getting on board a few minutes early ensures you can choose the ideal spot on the boat for optimal views and comfort.
Dress for the weather
Bring layers and protective clothing, especially if you plan to stay on the deck; weather conditions can change quickly on the water.
Bring your camera
Capture breathtaking shots of the Chicago skyline, navy pier, and Lake Michigan during the tour.
Book in advance
Private tours are popular, so reserving ahead guarantees your preferred date and time are secured.
Sunscreen
Protect your skin from UV rays during sunny outdoor hours on the water.
summer
Hat and Sunglasses
Shield your eyes and face from the sun for added comfort.
summer
Light Jacket or Layered Clothing
Stay warm and comfortable during cooler months or windy conditions.
spring|fall|winter
Camera or Smartphone
Capture stunning views of the Chicago skyline and Lake Michigan throughout the tour.