Ports of Call: Chicago, Illinois

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For this series on iconic ports of call, we’re highlighting nine cities that have leveraged their more industrial past to flourish into world-renowned, waterfront destinations. Several travel professionals share suggestions on where to go, what to see and what to do in order to fully appreciate these maritime metropolises.


A city crafted by man, fire and water, Chicago is known for its sky-scraping architecture, eclectic neighborhoods, midwestern hospitality and formidable winters. Chicago is known as the birthplace of modern architecture. After the fire of 1871, architects flocked to the city to take part in the rebuilding efforts. New building techniques and safety restrictions made way for the invention of the skyscraper. But what may surprise some travelers is how much Lake Michigan influences the city and its inhabitants. A protected lakefront gives Chicago 15 miles of bathing beaches and 19 miles of lakefront bicycle paths, and the lake’s oceanic waters provide ample opportunities for boating and other water sports. “Travelers are always amazed by our expansive Lake Michigan, our beaches, marinas and lakefront,” says Marc Anderson, director of marketing at The Peninsula Hotel.

Chicago Bucket List

  • River Cruise: “Chicago is a city given a second chance in many ways, but the most apparent is its architecture,” says Judson Corrie, concierge ambassador of the Waldorf Astoria. “A river cruise right through the middle of the city is simply the best way to appreciate it.”

  • Millennium Park: Highlights include Pritzker Pavilion, Anish Kapoor’s Cloud Gate (affectionately known as “The Bean”), Crown Fountains and Lurie Gardens, says Anderson.

  • Deep Dish Pizza: Locals are sure to have their favorites, but Corrie suggests trying this Chicago staple at Giordano’s, Pizano’s or Pequod’s.

  • The Art Institute of Chicago: Home to one of the largest and most extensive collections of Impressionist and Post-Impressionist paintings in the world.

  • Live Music: Jazz and blues are the stars of the city’s music scene. Check out Green Mill Cocktail Lounge, a historic jazz club dating back to the 30s.

This article is an excerpt from the July, August, September edition of the Traveler magazine. Click here to access the full issue.

By Hideaway Report Staff
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