Discover Chicago from a new angle aboard a private pontoon boat. This 2-hour cruise offers stunning views of the city skyline and Lake Michigan, perfect for relaxation and sightseeing.
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Difficulty
easy
Duration
2 hours
Fitness Level
Suitable for most fitness levels; minimal physical activity required
Wildlife
History
Chicago's waterfront has been a vital port since the 19th century, shaping the city's development and skyline.
Conservation
Chicago Boat Rentals promotes environmentally conscious practices to minimize impact on Lake Michigan's ecosystem.
Chicago Boat Rentals
Discover Chicago from a new angle aboard a private pontoon boat. This 2-hour cruise offers stunning views of the city skyline and Lake Michigan, perfect for relaxation and sightseeing.
Chicago Boat Rentals offers private boat and yacht experiences operating from Chicago, Illinois, with a range of self-drive and crew-assisted options. The company provides multiple vessel types including 22 ft and 18 ft pontoons that customers can drive after receiving on-board training, a private luxury yacht with a 12-person maximum, and a 41 ft Regal yacht for larger private charters. Guests may bring their own snacks and drinks (BYOB) on most trips, and catering is available as an add-on for select charters.
Evening fireworks cruises run seasonally on Wednesdays and Saturdays from Memorial Day to Labor Day, providing direct views of the Navy Pier fireworks during those scheduled nights. Boat training is included for self-drive pontoons so guests can take the helm with crew guidance. The luxury yacht options include features such as multi-deck viewing areas, a mid-deck with kitchen and entertainment space, and a swim platform on suitable vessels.
In addition to Chicago-based boat rentals and yacht charters, the business offers a Stand Up Paddleboard Lesson & Eco Tour listed for the Jersey Shore location, designed for beginner-friendly instruction and wildlife viewing for participants ages 12 and up. All trip descriptions specify passenger limits and basic amenities to help customers choose the right experience for their group. Reservations and scheduling details are provided per trip, including duration and guest capacity information.
Based In
Chicago, IL
Central riverfront location
Tours Offered
6 distinct trips
Pontoons, yachts, SUP, and cruises
Fireworks Nights
Wed & Sat (Memorial–Labor Day)
Seasonal evening cruises
Max Capacity
Up to 12 guests
Private luxury yacht seats 12
Select a self-drive pontoon, private luxury yacht, or evening fireworks cruise — check availability and book the ideal water experience today.
Arrive early to secure your spot
Arranging your reservation in advance ensures you get the time and boat size you prefer, especially during peak season.
Bring sun protection
Apply sunscreen and wear hats or sunglasses to shield yourself from direct sunlight during the cruise.
Pack a light jacket for cooler moments
Even summer days can have breezy evenings on the water, so bring a jacket or wrap to stay comfortable.
Capture the skyline at sunset
Timing your cruise to coincide with sunset can provide breathtaking photo opportunities of Chicago’s illuminated skyline.
Sunscreen
Protect your skin from UV rays during daytime cruises on open water.
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Hat or cap
Provides shade and additional sun protection.
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Light jacket or sweater
Keep warm during cooler parts of the day or season.
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Camera or smartphone
Capture stunning views of the Chicago skyline and Lake Michigan.