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Hotel Sax Chicago
Chicago, IL

From $339 per night
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The James Chicago
Chicago, IL

From $239 per night
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Chicago
Chicago

Picture New York City, with its diverse neighborhoods, fine dining, shopping, and handsome stone architecture. Now slow it down a bit and plop it down in the middle of the approachable, friendly mid-west. You’d have a city very much like Chicago, where you can find big fun without a big attitude. Consider timing your visit to coincide with the annual Taste of Chicago, the world’s largest food festival.

Activities and Attractions:
One of Chicago’s greatest pleasures is eating, and another is exploring the city’s various neighborhoods. Luckily, these pursuits are easy to combine. Chicago’s signature nosh is deep-dish pizza, which may sound a little lowbrow, but in this city, pizza is nearly an art form. You can find it just about anywhere, but the Near West Side, a formerly exclusively Italian enclave, would be a good place to look. (It’s more Greek now, so go ahead and indulge a gyro or souvlaki craving if you suddenly feel like that instead.)

Artsy Wicker Park, where many of the city’s German immigrants once found homes, might be a good place to try a Chicago-style sausage. The Pilsner neighborhood, full of brightly colored murals, is home to a large Mexican-American population and would be a good place for pozole. Not sure what you’re in the mood for? Try Rogers Park, near Loyola University, where you could have a bagel for breakfast, authentic Chinese food for lunch, and Indian chaat for a snack. For dinner, you’ll probably want something a little more upscale, so try one of Chicago’s three fine dining neighborhoods: fashionable Lincoln Park, newly-arrived River North, or the Miracle Mile, home of all things luxurious.

One other major Chicago attraction is its shopping scene. Shopping in Chicago can almost be summed up in two words: Miracle Mile. This chi-chi stretch of North Michigan Avenue contains an unbelievable concentration of high-end stores. Scanning the street is like reading a fashion week roster. Chanel, Armani, Tiffany, Burberry, Salvatore Ferragamo, and Kenneth Cole New York all have outposts here.

The Miracle Mile, in fact, packs in so much shopping that some of it has to be stacked on top of itself. At 900 Michigan Ave, you’ll find a vertical shopping mall overflowing with more big names, like Gucci, Lalique, and Max Mara. To cap it all off, at the very end of North Michigan Avenue, you’ll turn the corner onto Oak Street’s singular concentration of shops, including Robert Clergerie, Kate Spade, and Frette linens.

If you feel like you need to stop yourself from acquiring more, go to a place where the wares are only for looking, like the Art Institute of Chicago, Field Museum of Natural History, Museum of Science and Industry, or the excellent Shedd Aquarium. Finally, don’t leave Chicago without seeing some of the sights, like the Lake Michigan view from the end of the Navy Pier, or the cityscape and four-state view from the Sears Tower, currently the tallest building in America. New York City can’t beat that.

Insider Tip:
Want to loudly and clearly label yourself an outsider? Order a plain hot dog, or worse, one with ketchup. One legacy of the city’s German heritage is that the locals take brats, wursts, wieners, and all forms of “sassage” very seriously, and so should you. In Chicago, mustard barely qualifies as a condiment and ketchup is virtually taboo. Instead, pile on some vegetables, the more pungent and briny, the better. Common toppings include tomato, sweet relish, pickles, onions, and hot peppers. Insert your own “Chicago Fire” joke here.




-Exclusively for Perfect Escapes by Nicole Clausing
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