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Hip Wicker Park has been a residential enclave since Chicago was incorporated as a city in 1837. North Milwaukee Avenue is known for its bustling nightlife, dining and entertainment venues, with Double Door, Subterranean and Davenport’s setting the bar for the city’s trendy music clubs. North Damen Avenue draws hip crowds with its quirky shops, minimalist cafes, specialty grocery stores and cool fashion boutiques.

The Near North Side is home to iconic skyscrapers like the 1920s Wrigley Building, as well as 360 Chicago, a 94th-floor observation deck. Both are on the “Magnificent Mile” section of North Michigan Avenue, along with posh boutiques and department stores. The Navy Pier lakefront attraction has rides, casual dining, and cruises, and the huge Museum of Contemporary Art stages innovative exhibitions.

The Loop is a vibrant area featuring eclectic eateries, shops, theaters and parks. Comprised mostly of high-rises, it’s also home to the 108-story Willis Tower. The iconic “Cloud Gate” sculpture sits in Millennium Park. Grant Park features the large, rococo-style Buckingham Fountain and the renowned Art Institute of Chicago, and hosts annual events like The Taste of Chicago and Lollapalooza.

Mostly residential and collegiate, the Near West Side is home to Maxwell Street, the birthplace of Chicago Blues and the Polish sausage sandwich. Nearby is a long-running Sunday market and Hull House museum, a former immigrant settlement founded by reformer Jane Addams. Michael Jordan made his name at the United Center, where the Bulls and Blackhawks play. Italian restaurants cluster on Taylor Street in Little Italy.

00:00 Wicker park to Near north
30:30 Near North to loop
33:00 loop to near west side