To take in the vibrancy and rich Chicago culture, you must get to know these top neighborhoods.

Chicago Neighborhood Guide

If you’ve booked your flights to Chicago and want to explore the city, then this concise breakdown of the diverse neighborhoods of the Windy City will sure come in handy.


Considered the hippest and trendiest neighborhood in Chicago, Bucktown has become nationally recognized as one of the most artist-friendly areas in the US. In the 1980s, it became a sanctuary for artists who took advantage of the area’s cheap rent and proximity to downtown. Today with trendy bars, hip galleries, and unique architecture, the artist’s culture remains.

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Gold Coast

Elegant Residence in Gold Coat section of Chicago

Oprah once lived in this affluent neighborhood, whose five-star dining and plush shopping draw in the fashion-savvy and wealthy. The Oak Street Beach is arguably the best beach in Chicago and offers surreal, stunning views of Chicago and the lake. Best of all? The view of Hugh Hefner’s original playboy mansion on State Street.


An enormous and sprawling neighborhood, Chicago’s Lakeview is a diverse, nostalgic, and endlessly entertaining place to be. Home to Wrigleyville, the Cubs’ stomping ground, Boystown, one of the most vibrant LGBTQ communities in the world, and DePaul University, the area is quintessential Chicago. Go Cubs!

RELATED: Looking for the best form of transportation to get around Chicago’s famous neighborhoods? Read this post about Getting Around in Chicago!

Old Town

well preserved houses, Old Town Chicago

It comes as no surprise that Chicago’s Old Town is also its historic center. Home to some of the only buildings to have survived the Great Chicago Fire, Old Town’s rich history is rivaled only by its diverse brewing scene. For those looking for a taste of beer, either in an urban tavern or a refurbished speakeasy, Old Town is the place to be.

Has this list tempted your taste buds for the Windy City? Don’t waste time – start looking for cheap flights to Chicago and get here ASAP!

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