5 ways to enjoy the Chicago River in Chicago

One of the most popular tours with visitors is just as revered by locals, and for good reason. There’s no better way to experience the Chicago River than afloat Chicago’s First Lady, where personable docents from the Chicago Architecture Foundation point out the city’s most notable buildings with spectacular detail while gently floating by.

The most affordable way to experience the Chicago River from aboard a boat. Painted taxi-cab yellow and making six stops along the Chicago River from Michigan Avenue to Chinatown, the vessels range in size and can save time between destinations. Alternatively, bring a picnic and ride all the way to Chinatown’s Ping Tom Memorial Park.

A handful of kayak companies operate along the Chicago River, but Wateriders is the oldest and most reputable. Rent a one- or two-person kayak for a minimum of two hours – the perfect amount of time to go with the river’s flow and check out the sites. Be mindful of boat traffic, which is busier on beautiful days.

The official flagship of the City of Chicago, Tall Ship Windy is a 148-foot four-masted schooner leading tours on the Chicago River and Lake Michigan. Unlike the city’s handful of speedboat and tourboat offerings, this elegant sailboat is powered by the wind in the Windy City (though was built with a backup engine just in case).

Grab a handful of friends and hire a captain. From May through October, it’s fairly affordable to charter a yacht for the afternoon (or evening) with companies like Knot My Boat, SunSea Yacht Charters, Come Sailing, and more. Many companies offer a range of boat sizes to suit a dozen guests to 100, with drinks and catering services optional.