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CHICAGO

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Chicago, IL 60601, USA
Visitors take their best Chicago photographs in front of the iconic Millennium Park sculpture called Cloud Gate (known colloquially as the Bean, for its shape). Conceived by British artist Anish Kapoor and constructed from 168 stainless steel...
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233 S Wacker Dr, Chicago, IL 60606, USA
Willis Tower—originally known as the Sears Tower—was the world's tallest building for 23 years until it was unseated in 1996 by the Petronas Twin Towers in Kuala Lumpur. The 110-story skyscraper is still mighty impressive. Its "bundled...
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6836 N Sheridan Rd, Chicago, IL 60626, USA
Ask any local where to try your first real deep-dish pizza and they'll say "Giordanos." It's obviously the best in town. Chicago-style pizza is unique and totally different than what you'll find in Italy. More like a pie, the crust is tall and...
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337 E Randolph St, Chicago, IL 60601, USA
I know, I know, Lollapalooza may be a little overpriced and overrated. But the truth is, it is still one of the best music festivals in the country. Amazing live performances by well-known artists and new talents, worldwide travellers, a quirky...
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Streeterville, Chicago, IL 60611, USA
The architectural boat tour of downtown Chicago is the single best way to see this city in a whole new way. From first-timers to lifers, it doesn't matter how long you've been in town, this perspective is going to be new to all. There are many...
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The transit systems for most big cities run underground, but Chicago’s elevated train runs largely above ground, and its railway around the downtown area gave it the nickname “The Loop.” I wish I could have seen the first version of the L, a steam...
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1060 W Addison St, Chicago, IL 60613, USA
Steeped in history, loved my many, loathed by some, and sorely in need of a championship, Wrigley Field is a true cornerstone of the always controversial sporting world. No trip to Chicago is complete without a visit to this monument to to...
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201 E Randolph St, Chicago, IL 60602, USA
The real voyage of discovery consists not in seeking new landscapes, but in having new eyes. ~ Marcel Proust. For my inaugural highlight on AFAR, I am starting with my wife's favorite quote, and a local sight in Chicago. Sometimes people feel they...
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565 W Jackson Blvd, Chicago, IL 60661, USA
Lou Mitchell’s diner has been open in the same location since 1923; so long, in fact, that diner patrons witnessed the heyday of Route 66, which started right here next to Union Station. The Chicago city council renamed Jackson Street “Lou...
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Old Town, Chicago, IL, USA
Located a short train ride from the Loop, this wrought-iron doorway marks the entrance to Chicago’s Old Town. You'll find plentiful shopping and restaurant options in the neighborhood, as well as St. Michael’s Church, one of the city's oldest...
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1230 W Greenleaf Ave, Chicago, IL 60626, USA
For the most relaxing beach experience, travel a short distance north on Lakeshore Drive and you will find idyllic beaches that you can have almost all to yourself. Here you'll feel free to play, exercise or take a romantic stroll away from the...