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The Perfect Weekend in Chicago

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Visitors with only three days in Chicago should maximize their time with ample art and food exposure. Orient yourself by taking an architectural cruise along the Chicago River or get high with a panoramic view of the city from the top of one of its fantastic buildings. Then hit up some of the world-class museums along the lakefront: A visit to the Art Institute, the Field Museum, and the Chicago Architecture Foundation can explain (in a spectacular fashion) the cultural breadth of the Windy City. See the Cubs play ball at Wrigley Field and drink a craft cocktail at one of our favorite bars. In just one long weekend, you'll get a vivid taste of Chicago, a city second to none.
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909 W Belmont Ave, Chicago, IL 60657, USA
In Chicago there are four Ann Sather locations that open at 7am and close between 3-4pm serving breakfast and lunch. There are a lot of options on the menu and they make a mean salmon dill omelette with smoked salmon from Norway; but really, you...
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900 Michigan Avenue, Chicago, IL 60611, USA
I thought New York was a good shopping city but Chicago has pretty much the same big name shops and they're spaced out. The 900 Shops was probably my favorite space in terms of cleanliness, space and quality of shops. The best J. Crew is here 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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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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800 N Michigan Ave, Chicago, IL 60611, USA
Outfitted in turquoise and chocolate patterned decor with a stellar view from the Park Hyatt Hotel’s 7th floor, NoMI is a cool tranquil oasis in the midst of the shopping extravaganza that is Michigan Avenue. And yes, it’s just as chic and swanky...
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140 E Walton Pl, Chicago, IL 60611, USA
You know you're somewhere special when your car pulls up in front of the The Drake Hotel, located right off of Michigan Ave. in downtown Chicago. A white gloved bellman opens the door and greets you in the most charming, old school way. As you...
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7705 N Eastlake Terrace, Chicago, IL 60626, USA
Pick up your morning coffee at one of the many local coffee shops, and walk to Rogers Beach (known by locals as Lighthouse Beach). The sunrise over Lake Michigan is stunning! Locals fish off the lighthouse pier in the early morning semi-darkness....
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220 E Chicago Ave, Chicago, IL 60611, USA
The interior architecture of Chicago’s MCA building is worth the price of admission. Four floors of exhibit halls branch off the central staircase pictured above, and the East and West facing glass walls have unparalleled views over Lake Michigan...
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1655 W Cortland St, Chicago, IL 60622, USA
To find the Trap Door Theatre, you walk down a narrow walkway between two white brick walls. A steel door opens onto the kitchen of Jane's Restaurant. A second door leads to a small black box theater. There, for the last 15 plus years, the Trap...
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51 W Jackson Blvd, Chicago, IL 60604, USA
Chicago’s beloved South Side hat shop, Optimo, recently opened a downtown location in the historic Monadnock building. A favorite of Johnny Depp and former Mayor Richard Daley, the new shop sells handmade felt fedoras and porkpies that appear to...
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1138 W Bryn Mawr Ave, Chicago, IL 60660, USA
Lovely, Too is a delightful little bakery up in Andersonville. They serve Intelligensia coffee, a Chicago brand, and their pastry case is drool worthy with incredible scones, cookies and cupcakes. It's rarely crowded and there are plenty of tables...
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20 N Upper Wacker Dr, Chicago, IL 60606, USA
Pass through the beautiful lobby and enter a world where your senses are immersed in soaring vocal art. The Lyric Opera of Chicago is a world-renowned music establishment that features the most famous voices on the globe. There are two on-site...
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15 E Ohio St, Chicago, IL 60611, USA
The Acme is my favorite hotel in Chicago. First off, most of the rooms are suites with tiny kitchenettes, refrigerators, microwaves and separate bedrooms. The “knock and drop” coffee feature means someone will bring you a thermos of hot coffee at...