Discover Chicago’s stunning skyline and Lake Michigan views on a private boat tour with Keywester. Perfect for special occasions or a relaxing day on the water, this experience offers personalized adventure and spectacular photo opportunities.
More ways to explore the area's outdoor wonders
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Difficulty
easy
Duration
1–3 hours
Fitness Level
Minimal physical effort required, suitable for all ages and fitness levels
Wildlife
History
Chicago’s lakefront played a vital role in the city’s development, historically serving as a busy port and recreational hub.
Conservation
The area promotes sustainability through protected habitats and eco-friendly boat practices to preserve Lake Michigan’s natural beauty.
Island Party Boat
Discover Chicago’s stunning skyline and Lake Michigan views on a private boat tour with Keywester. Perfect for special occasions or a relaxing day on the water, this experience offers personalized adventure and spectacular photo opportunities.
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.
Wear Weather-Appropriate Clothing
Make sure to dress in layers and bring rain gear if necessary, as weather on the lake can change quickly.
Bring Your Camera
Capture breathtaking views of Chicago’s skyline and Lake Michigan with ample opportunities for photography.
Arrive Early
Arriving at least 15 minutes before your scheduled departure ensures a smooth check-in and boarding process.
Stay Hydrated
Bring water and drinks to stay refreshed during your private cruise, especially on hot days.
Personal Camera or Smartphone
Capture stunning photos of Chicago’s skyline, lake views, and memorable moments.
Sunscreen
Protect your skin from sun exposure during daytime cruises.
summer
Hat and Sunglasses
Shield yourself from sun glare and stay comfortable during outdoor viewing.
summer
Light Jacket or Sweater
Keep warm during cooler days or evenings on the water.
spring|fall|winter