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175 N State St, Chicago, IL 60601, USA
Chicago has wonderfully rich theater scene ranging from intimate storefront theaters to the famous improv comedians at Second City and any number of Broadway shows. The Cadillac Theatre in the Loop has a beautiful, richly decorated house for large...
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78 E Washington St, Chicago, IL 60602, USA
Chicago's art scene is often overshadowed by the ever-increasing foodie scene but the Windy City offers just as much contemporary and historical art as pizzas and gourmet doughnuts. The Chicago Cultural Center is one of my favorite art-focused...
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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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1 N Michigan Ave, Chicago, IL 60602, USA
If you're visiting Chicago in the winter, be sure to make your way to one of the city's many ice rinks. For outdoor skating with a view, head to the McCormick Tribune Ice Rink in Millenium Park. The ice skating rink is sandwiched between Cloud...
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50 W Washington St, Chicago, IL 60602, USA
When the Christmas tree lights up the Daley Plaza, it’s a magical moment every year. Chicago’s tree lighting ceremony includes live music and theatre performances by the actors in A Christmas Carol and officially begins the holiday season in late...
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100 W Randolph St #4-300, Chicago, IL 60601, USA
Jean Dubuffet said he wanted this 20,000lb fiberglass sculpture to look like a drawing that extended into space incoporating architecture, animals, trees and portals. I get the drawing part but the rest of it depends on where you stand and look....
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50 W Washington St, Chicago, IL 60602, USA
The second most famous public sculpture in Chicago is 50ft high, made of steel and no one knows what it means. It’s doesn’t even have a proper name so it’s just known as “The Picasso.” Pablo Picasso gifted this untitled sculpture to the city of...
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600 S Michigan Ave, Chicago, IL 60605, USA
Chicago's Museum of Contemporary Photography occupies a small compact space with gorgeously designed photography exhibits on three floors. The current exhibit, called Dandy Lion, explores black masculine identity in photographs of sharply...
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301 S Columbus Dr, Chicago, IL 60605, USA
Officially open to the public way back in 1927, even after all these years, Buckingham Fountain remains one of THE must-see sights in Chicago. Sitting on the edge of Lake Michigan, and intermittently erupting with spires of water, Buckingham...
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1400 S Lake Shore Dr, Chicago, IL 60605, USA
Dinosaurs, pyramids, cave paintings, sharks—if you don't like the Field Museum then you must never have been a kid. Home to an extensive assortment of magical displays highlighting all facets of natural history from around the world, the...
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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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26 W Randolph St, Chicago, IL 60601, USA
A combination of sugar and salt, sweet and savory, there's nothing like Garrett's "Chicago Mix"—a combination of caramel corn and cheese popcorn. It's the kind of thing I crave in such a way that it's a good thing I don't live in Chicago....
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1616 N Wells St, Chicago, IL 60614, USA
The Second City has come a long way since the small cabaret theater that launched in 1959. As a sketch comedy and improvisational performance theater, the venue has been keeping people laughing for over 50 years. Situated in the historic Old Town...
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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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111 S Michigan Ave, Chicago, IL 60603, USA
Just imagine having 264,000 square-feet of modern art at your disposal seven days a week. That is exactly what you have if you visit the Modern Wing of the Art Institute of Chicago. Above is but one example of the funky-cool exhibits that await...
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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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Illinois Medical District, Chicago, IL, USA
Chicago is the king of comedy, hot dogs, and extreme Midwest weather. But since the Great Chicago Fire of 1871, the city has been reinventing itself. Today, clever design projects (such as “Color Jam,” shown) top the list of reasons...
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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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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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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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809 W Randolph St, Chicago, IL 60607, USA
West Randolph Street in Chicago’s West Loop has become a new home to the city’s culinary talents. Stephanie Izard first drew crowds cooking dishes like roasted pig face at Girl & the Goat (the restaurant pictured above)....
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1400 W Randolph St, Chicago, IL 60607, USA
This drink was amazing, as always, with Peter V behind the stick. The man with the plan behind beverages collaborating with the marvelous Chef Bill Kim, BellyQ has been popular since before it opened! Artfully devised drinks, a sensational...
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1466 N Ashland Ave, Chicago, IL 60622, USA
Schwa is kind of a difficult place to describe; it's such an eclectic bundle of everything, you just have to experience it for yourself. The exterior of the building makes it look like it should be condemned, but it's actually structurally sound....
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619 W Randolph St, Chicago, IL 60661, USA
When it opened doors in 1998, this West Loop destination helped pave the way for Restaurant Row and all of the gastronomic glory that would follow. Ever since, Blackbird's been filling seats (intimate banquette seating, thank you) with diners...
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953 W Fulton Market, Chicago, IL 60607, USA
Next is famous for its ever-changing theme menus. The most recent is "The World's 50 Best Restaurants," featuring dishes created by the world's best chefs and curated by the Next team. When I was there we ate the centerpiece, and the floating...
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449 N Clark St, Chicago, IL 60654, USA
Rick Bayless opened his upscale Mexican restaurants Frontera Grill and Topolobampo in the late 1980s and then won a litany of James Beard Awards, including Outstanding Restaurant (in 2007 and 2017). He took the top spot in the first season of Top...
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1747 N Damen Ave, Chicago, IL 60647, USA
Hot chocolate isn’t the only thing Mindy’s has going for it, although the varieties are epic. Mexican chocolate with spicy cinnamon, French chocolate made with 72 percent cacao, and Belgian chocolate mixed with mint, chai, and...more...
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500 N Michigan Ave, Chicago, IL 60611, USA
The chefs of top Chicago restaurants Spiagga, Mia Francesca and Heaven on Seven came together to collaborate on one restaurant and I think The Purple Pig is better than all their other restaurants. Specializing in Mediterranean food served tapas...
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130 E Randolph St, Chicago, IL 60601, USA
Tavern at the Park is an amazing foodie destination in downtown Chicago. The menu is full of delicious creations, including some nice variations on classic dishes. I found their wings (which are rubbed and then grilled, not fried) to be amazing,...
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800 W Randolph St, Chicago, IL 60607, USA
Why the best burger in Chicago is served at a bar with a French name might be a question for the ages. But rather than question it, just go there! The single burger at Au Cheval is actually a double, and don't even ask about the double...
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1545 N Damen Ave, Chicago, IL 60622, USA
Brought to you by the guys who own Big Star Tacos down the street, Dove’s Luncheonette channels the spirit of a retro lunch counter and the soul of Southern-Mexican fusion food. The menu includes Mexican classics like chili rellenos and...
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116 N Green St, Chicago, IL 60607, USA
RM Champagne Salon is another bright light on Chicago’s Randolph Street restaurant row. It’s a gorgeous space with exposed brick walls, vintage furnishings and soft lighting, a delightful romantic date spot. The compact menu has a...