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The 7 Best Boat Tours in Chicago

Merchant List Map
Near North Side: Tours, Tastings, and Taxis

Wendella’s boats have sailed Chicago’s waters since 1935, when founder Albert Borgström built the company’s first ship by hand. Still run by Albert’s great grandson, Michael, the company complements its time-tested architecture and history tours with specialty tours that feature beer and barbecue, wine and cheese, or fireworks. Wendella also operates Chicago’s distinctive yellow-and-black water taxis.

The Loop: Chicago Architecture Foundation’s Official Tour

Aboard Chicago’s First Lady and its sister vessels, Chicago Architecture Foundation–certified guides expound on the history of more than 50 buildings along the river. Each boat is equipped with bars and climate-controlled lower cabins.

Near North Side: Leave Chicago in Your Wake

Seadog Cruises’ speedboat tours zip along Lake Michigan at up to 45 mph, infusing a dose of adrenaline into 30-minute jaunts. They also offer slower 75-minute trips that show off architectural landmarks along both the lake and the river.

Near North Side: Nighttime Tours

Shoreline Sightseeing’s ships set off from Navy Pier, sailing southward to showcase buildings such as the Tribune Tower, the Wrigley Building, Marina City, and more than 40 other downtown staples. Its architectural tours depart day and night, offering the option to see the city skyline shimmering beneath the sun or aglow in the evening.

Near North Side: Complimentary Starbucks and Snacks

Chicago Line Cruises’ docents are well versed in the city’s history and architecture, but the company’s cruises range from fully narrated architectural tours to partly narrated cocktail affairs to unnarrated fireworks cruises on Saturdays. Onboard the vessels, guests can enjoy complimentary Starbucks coffee, Twinings tea, and fresh muffins and cookies.

South Loop: Blast from the 1800s

Not far from Soldier Field, the tall ship _Red Witch_ embarks on freewheeling cruises, guided less by a strict itinerary than by the whim of the wind. Constructed in 1986, its oak and mahogany hull is a historically accurate reproduction of the John Alden schooners that once prevailed in the Great Lakes.

The Loop: Dog-Friendly Cruises

Dogs aren’t known for their appreciation of architecture, but they definitely enjoy a crisp breeze. In addition to its standard human-friendly tours, Mercury, the Skyline Cruiseline offers canine cruises with historical and architectural trivia for people and water bowls for pups.