Chicago by the Water

Chicago by the Water

Drink in Chicago’s city views from a watery vantage – be it sailing on Lake Michigan or cruising along Chicago River, here’s how to enjoy Chicago by the water.

Chicago’s major draw-card is its jaw-dropping architecture, and there’s no better way to take it all in than from the breezy open-top comfort of Chicago's First Lady, a river cruise helmed by docent guides from the nonprofit Chicago Architecture Center. This insightful 90-minute jaunt tells the story behind more than 50 historic buildings, revealing the city’s 100-year transformation from rustic settlement to gutsy Art Deco dame. A twilight option is available for that extra sparkle.

For a more exclusive experience, speak to The Peninsula concierge about the hotel’s private package, River Tour of Chicago’s Skyscrapers. All aboard the gorgeous, 48-ft polished mahogany yacht, Lady Grebe, where 2-4 guests can enjoy 90 minutes of the city’s most iconic buildings and historic architectural landmarks, customizable based on special interests, plus a 5-star lunch with bubbles, served by a Peninsula butler.

For watery adventures from the vantage of solid ground, take a walk along the Lakefront Trail, an 18-mile stretch that traverses through four parks, including Lincoln Park and Zoo, Millennium Park and 13 neighbourhoods among other attractions, while affording grandstand views of the Great Lake and city. Alternatively, shed some of those deep-dish calories with an easy-breezy cycle ride along the waterfront; there are four bike/Segway stations between Foster Beach and Millennium Park.

Chicago's First Lady / Chicago Riverwalk (look for the blue awning) / N Michigan Ave & E Upper Wacker Dr / +1 847 358 1330 / approx every hr / architecture.org

River Tour of Chicago’s Skyscrapers / The Peninsula Academy / +1 312 337 2888 / book at least two weeks in advance / academypch@peninsula.com /peninsula.com 

Lakefront Trail / W Armitage Ave & N Clark St