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Top Chicago Boat Rentals

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Chicago Private Rental Yacht Charter

S. Silvera Charters offers a unique luxury yacht rental for those looking to create unforgettable memories on the water. Perfect for special events or leisurely cruising, this charter allows you to set your own schedule and enjoy a personalized experience. With a minimum rental of three hours, you can relax on board while exploring beautiful coastal views. Captain's fees are separate, ensuring a tailored experience for your group. - Exclusive yacht rental for luxury experiences - Flexible scheduling with afternoon and evening options - Minimum three-hour rental for ample exploration - Personalized service with optional captain at an additional fee

Chicago Private Rental Yacht Charter

3 to 8 hoursFree Cancellation

from $1,300

Likely to Sell Out

Join us in the daytime or evening for City lights and breathtaking views

Get a front row perspective on the exquisite buildings that line the Chicago River during a 45-minute architecture cruise. Hear live commentary about the history and architectural heritage of Chicago on this family-friendly tour, which highlights landmarks such as the Chicago Riverwalk, Michigan Avenue Bridge, Wrigley Building, and Willis Tower. Sit on the open-air top deck or the sheltered bottom deck for the ultimate view of Chicago.

Chicago River 45-Minute Architecture Tour from Magnificent Mile

45 minutesFree Cancellation

Chicago Architecture River Cruise

Admire some of the Windy City's most iconic views—and enjoy a time-saving, relaxing way to sightsee—aboard this pet-friendly Chicago River architecture boat tour. With commentary from your onboard guide, watch the spectacular skyline glide by, including dozens of notable buildings, like the Wrigley Building and the John Hancock Building. In just one tour, you cover multiple branches of the Chicago River and learn insider facts and stories you'd otherwise miss.

Chicago Architecture River Cruise

1 hour to 1 hour 30 minutesFree Cancellation

Chicago's Lake Michigan Downtown Kayak Rental at Ohio Street Beach

Escape the bustle of the city during this one or two-hour kayak rental along Lake Michigan in downtown Chicago. Experience the serene waters of the iconic lake as you paddle at your own pace in a single or tandem kayak, enjoying views of Chicago’s famous skyline. Take breaks along nearby urban beachfronts, with the option to extend your rental time. Stand-up paddleboards are also available for rental.

Chicago's Lake Michigan Downtown Kayak Rental at Ohio Street Beach

1 to 2 hoursFree Cancellation

Lake Michigan 30-Minute Speedboat Ride

Zoom along the shoreline of Lake Michigan, zipping past famous landmarks as you go, during this exhilarating speedboat ride in Chicago. Climb aboard your 2,000-horsepower speed boat at Navy Pier, then hang on for the ride of a lifetime, as you zip past famous attractions like the Willis Tower, Grant Park, and Buckingham Fountain, pausing to learn a little about the history and architecture of the Windy City along the way.

Lake Michigan 30-Minute Speedboat Ride

30 minutesFree Cancellation

Likely to Sell Out

Explore Chicago's legendary architecture and history.

Discover the architectural gems of the Windy City from an ideal vantage point—and learn insider facts and stories about the city's top attractions—on this Chicago River cruise. Travel in comfort aboard a boat equipped with both indoor and outdoor seating areas. Covering more than 130 years of architectural history, this tour is the perfect opportunity to see a huge area of the city without the hassle of taxis and public transit.

Chicago River 90-Minute Architecture Tour

1 hour 30 minutesFree Cancellation

Likely to Sell Out

This tour cruises the Chicago River and Lake Michigan.

Chicago Lake and River Architecture Tour

1 hour 30 minutesFree Cancellation

Chicago Full Day Bike Rental

Discover Chicago's many delights from the comfort of two wheels. Simply pick up your full-day bike rental with lock, map and helmet and start exploring, either solo or with friends. Make your way through Millennium Park and to historic Wrigley Field, stop for a visit at Navy Pier or spend a couple hours watching sea turtles, penguins and even a piranha at Shedd Aquarium. You get to tour Chicago independently at your own pace and leisure without having to deal with parking or public transit.

Chicago Full Day Bike Rental

1 dayFree Cancellation

Top Attractions in Chicago

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The statue of a lion at the entrance to Art Institute of Chicago, USA

Attractions

Art Institute of Chicago

Tour boats running on Chicago River on a sunny day

Attractions

Chicago River

The red velvet seats and bohemian interior of the Chicago Theater.

Attractions

Chicago Theatre

A woman exploring the view from the Skydeck Chicago at Willis Tower.

Attractions

Skydeck Chicago at Willis Tower (Sears Tower)

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