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AFAR's Guide to Lollapalooza: 24 Chicago Summer Destinations

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The 22nd annual music festival takes place August 2nd-4th in Chicago's Grant Park. Once the last song has been sung, and the exclusive after parties are over, make the most of your Chicago stay: eat, drink and explore your way through the Windy city. With iconic theaters, historic architecture, miles of stunning lakefront, a rowdy sports scene and more food than you'll know what to do with, Chicago has something for everybody, especially in the summer!
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100 W Ontario St, Chicago, IL 60654, USA
One of the best fast food chains in the States has to be Portillo's Hot Dogs. With 48 stores exclusive to the Chicagoland area, it's a must-stop while visiting the city. Eating in or driving through, you can enjoy the timeless local classic -the...
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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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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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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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111 S Michigan Ave, Chicago, IL 60603, USA
See our full list of Where to Go in 2015. The Art Institute of Chicago hosts the first exhibition devoted to Britain’s rising-star architect David Adjaye in September. Also in the fall, the world’s leading design talents will gather for the...
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Lincoln Park, Chicago, IL, USA
While some restaurants use being rude as their gimmick, the women at the Wiener Circle in Lincoln Park are the real deal. These “bitches” as they affectionately call themselves (I call them verbal assassins) will not hesitate to call you out and...
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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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1200 S Lake Shore Dr, Chicago, IL 60605, USA
My three year old was fascinated by the Jellies Exhibit—one of many engaging displays—at the Shedd in Chicago. What a joyful moment, capturing the wonder of a young mind.
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2900 W Belmont Ave, Chicago, IL 60618, USA
Back in 2010 Lady Gaga tweeted that she loved the burgers at Kuma’s Corner and today there are still waiting lines out the door just to have lunch. You think that’s the Gaga or the burger? I know that we waited for a good hour to get a table at...
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Illinois Medical District, Chicago, IL, USA
The Wrigley Building
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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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600 E Grand Ave, Chicago, IL 60611, USA
Most visitors to Chicago see it from only one perspective: from the city looking out over the water. But what would it look like if your vantage point was from out over the water looking down at the city? Just a little bit north of Chicago there...
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163 W North Ave, Chicago, IL 60610, USA
Chicago may be known for its deep dish, but it's just as easy to rustle up a jumbo slice — without having to pay extra for a soda. The slices at Bacci Pizzeria are as big as any you'll find in New York City. A slice and soda cost $5, except on...
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816 W Randolph St, Chicago, IL 60607, USA
Randolph Street in Chicago boasts a plethora of choices when it comes to excellent cuisine. De Cero is but one of places where you can go with a group of friends and feel like you are right at home. With an impressive selection of tequilas, and...
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2519 N Halsted St, Chicago, IL 60657, USA
B.L.U.E.S. is not a big bar, but they play plenty of great blues (and have been voted best blues club on Chicago's North Side). Primarily local artists play in this comfortable, intimate setting. If you want a seat, push way in past the stage and...
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Lincoln Park, Chicago, IL, USA
Chicago is one of my favorite cities in the USA. It's bursting at the seams with fantastic restaurants, hole-in-the-wall pubs and bars, world-class stadiums, art galleries, and everything else you'd expect in an Alpha World City, though it retains...
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1531 N Damen Ave, Chicago, IL 60622, USA
Everyone knows Big Star is famous for its cheap and tasty tacos but it's the queso fundido that really wowed my tastebuds. Melted queso Chihuahua cheese compliments the peppers and meaty chorizo in this dish. I didn't even use the tortillas. It's...
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2391 N Stockton Dr, Chicago, IL 60614, USA
Lincoln Park is a wonderful green area nearing Lake Michigan in Chicago. It has a Zoo free to the public as well as green lawns and flower beds. Near the North end is the multiple room conservator. Like the rest if the park it is open free to the...
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2021 N Stockton Dr, Chicago, IL 60614, USA
The Patio at Cafe Brauer is a great place to relax over a cold brew while taking in the scene of a nearby nature walk and pond with the city skyline in the distance. A respite to enjoy the energy of people out enjoying their diverse city,...