Illinois

A Comparison of Chicago Private Boat Tours

by Cedric Pentonville  |  Published April 24, 2023

Set beside the mighty Lake Michigan and bisected by rivers, Chicago is the perfect place to take a private boat tour.

(Photo: Viator.com)

Chicago is a great city for anybody who loves being out on the water. Five rivers plus their tributaries flow through the wider urban area, while all the city’s major sights sit flush with the shoreline of Lake Michigan. Speedboats, yachts, liners and all manner of waterborne vessels are common sights. Chartering one of your own for a few hours is the best way to see the Windy City in style, while maintaining privacy for you and your travel companions. Here’s a look at three great options.

Chicago Kayak Rental at Ohio Street Beach

By far the best value way to get out onto the water in Chicago is with a self-guided kayak rental, such as this option from Bobby’s Bike Hike. Choose between solo or tandem kayaks and pay by the hour. The rental store is right between Ohio Street Beach and the point where the Chicago River meets the lake, ideal for some of the best sightseeing in Chicago, especially if you paddle further out and look back towards the shore, where the skyline looms massive over the water. From $50 per person.

Book at Viator.com

(Photo: Viator.com)

Two-Hour Private Architecture Boat Tour

There are many Chicago cruises and ferry tours, but the large groups of people mean itineraries are fixed and generalized to appeal to everyone. To tour the Chicago sights that you’re keenest on seeing, this private tour is the ideal way to go. Tours depart from DuSable Harbor, at the north end of Grant Park, and generally head as far south as Hammond, Indiana, before heading back to Chicago. Departures are available daily for any time that suits you and your travel companions between 9am and 9pm. The price includes tax and your captain, and covers up to six people. From $700 per group.

Book at Knockoutcharters.com

Private Sightseeing Cruise in Chicago

An even classier type of charter option in Chicago is this 46-foot (14m), private Italian yacht. If you’re looking for a great value hire, then this fee, which covers your captain, yacht and three hours out on Lake Michigan, really starts to seem like a great deal for bigger groups. Up to 13 passengers are allowed on board, with sun decks up top and out front providing ample space to catch the sun or sightsee. Plus, you can bring your own food and drinks on board, making it a great choice for birthdays, bachelor and bachelorette parties, and many other celebrations. From $1,800 per group.

Book at Viator.com