VIDEO: How to Spend One Perfect Day in Chicago
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VIDEO: How to Spend One Perfect Day in Chicago

Even if you only have a few hours to kill, it’s impossible to run out of fun things to do in Chicago. Pro-traveler Jamie McDonald visited the Windy City to experience firsthand just how much you can cram into one (ambitious) day.

Begin your tour of the city at the Chicago Athletic Association Hotel—one Travel + Leisure’s favorite new hotels. The historic Venetian-Gothic building (built for the 1893 World’s Fair) has been transformed into a luxury property with a clubby vibe and hip receptionists. Drop your bags in the Roman & Williams-designed masculine, wood-and-leather rooms and head to The Games Room for bocce, shuffleboard, or pool.

If you’ve worked up an appetite, take a bite out of the city’s greatest export: deep dish pizza. The epic pie was born here, and there’s no better place to sample the local specialty than Pizano’s or Giordano’s. Go all-out at the latter with the stuffed Chicago Classic, which is loaded with pepperoni, mushrooms, onions, and green peppers. It’s hardly a wonder than Chicago is one of America’s Best Food Cities.

What do in Chicago on a beautiful day? Head straight to Millennium Park. After you’ve taken an obligatory selfie of yourself reflected in Anish Kapoor’s gleaming, stainless steel Cloud Gate sculpture, get a culture fix at The Art Institute of Chicago. There are more than 300,000 works of art scattered throughout the eight buildings.

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For the best views in the entire state of Illinois, you can visit either the Willis Tower Skydeck (which provides panoramic views of the city from the 103rd-floor) or the John Hancock Tower: now known as 360° Chicago. Here, you can peer out over The Magnificent Mile from 1,000-feet up, and enjoy a sunset cocktail from your lofty perch.

The most difficult decision you’ll have to make is where to eat and drink in Chicago, as the options are seemingly endless. Momotaro, a three-story sushi and robato spot, is one of the best restaurants in town. Order the Japanese tomato and Maui onion “tartare” to start. End the night with a tropical cocktail at Three Dots and a Dash—one of the city’s best undercover bars. They’re taking tiki to a whole new level of chic.

For a fix of fresh air before your departing flight, take a stroll along the Chicago River. It’s the only river in the world that flows backward.

Is it any surprise this trailblazing city is the third most-visited city in the country?

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