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Chicago, Illinois
Chicago is the home of the blues and the truth of jazz, the heart of comedy and the idea of the skyscraper. Here, the age of railroads found its center, and airplanes followed suit. Butcher of hogs and believer in progress, it is one of the world’s great cities, and yet the metropolitan luxuries of theater, dining, and shopping have barely put a dent in real Midwestern friendliness. It’s a city with a swagger, but without the surliness or even the fake smiles found in other cities of its size.

As the hub of the Midwest, Chicago is easy to find — its picturesque skyline calls across the waters of Lake Michigan, a first impression that soon reveals world-class museums of art and science, miles of sandy beaches, huge parks and public art, and perhaps the finest downtown collection of modern architecture in the world.

With a wealth of iconic sights and neighborhoods to explore, there’s enough to fill a visit of days, weeks, or even months without ever seeing the end. Dress warm in the winter, and prepare to cover a lot of ground: the meaning of Chicago is only found in movement, through subways and archaic elevated tracks, in the pride of tired feet and eyes raised once more to the sky.

Chicago Neighborhoods
Many visitors never make it past the attractions downtown, but you haven’t truly seen Chicago until you have ventured out into the neighborhoods. Chicagoans understand their city by splitting it into large “sides” to the north, west, and south of the central business district (the Loop). Chicagoans also tend to identify strongly with their neighborhood, reflecting real differences in culture and place throughout the city. Rivalries between the North and South Sides run particularly deep, while people from the West Side are free agents in critical issues like baseball loyalty.

Downtown (The Loop, Near North, Near South)
The center of Chicago for work and play, with shopping, skyscrapers, and the city’s most famous travel sights

North Side (Lakeview, Boystown, Lincoln Park, Old Town)
The city’s best theaters, a ton of bars and clubs, one of the largest LGBT communities in the nation, and the Friendly Confines of Wrigley Field

South Side (Hyde Park, Bronzeville, Bridgeport-Chinatown, Chatham-South Shore)
The historic Black Metropolis, brainy Hyde Park and the University of Chicago, Chinatown, the White Sox, soul food, and the real Chicago blues

West Side (Wicker Park, Logan Square, Greektown, Pilsen)
Ethnic enclaves, dive bars, and hipsters abound on the fashionably rough side of town

Far North Side (Uptown, Lincoln Square, Rogers Park)
Ultra-hip and laid-back, with miles of beaches and some of the most vibrant immigrant communities in the country

Far West Side (Little Village, Garfield Park, Humboldt Park, Austin)
So far off the beaten tourist track you might not find your way back, but that’s OK given all the great food, a couple of top blues clubs, and enormous parks.

Southwest Side (Back of the Yards, Marquette Park, Midway)
Former home to the massive meatpacking district of the Union Stockyards, huge Polish and Mexican neighborhoods, and Midway Airport

Far Northwest Side (Avondale, Irving Park, Portage Park)
Polish Village, historic homes and theaters, and some undiscovered gems in the neighborhoods near O’Hare International Airport

Far Southeast Side (Historic Pullman, East Side, Port of Chicago)
The giant, industrial underbelly of Chicago, home to one large tourist draw: the historic Pullman District

Far Southwest Side (Beverly, Mount Greenwood)
Ireland in Chicago: authentic Irish pubs, brogues, galleries, and the odd haunted castle, all extremely far from the city center

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