Get a vivid impression of each city neighborhood through travelogue-quality descriptions, photo galleries, online videos, and our exclusive Chicago Explorer interactive map and business directory.
Chicago homes include an amazing array of properties, from vintage single-family homes to luxury condos.
The iconic Chicago skyline and modern cityscape have evolved from a long history of architectural innovations, progress-minded city planners, and concerted efforts to merge metropolitan life with the natural beauty of the land. Beyond the city’s distinctive profile is a diverse population of 2.8 million residents who compose the city’s heart and soul. A multicultural community from across the country and the world have made their homes in Chicago, shaping the sprawling urban center into over 183 separate Chicago neighborhoods.
Chicago’s beginnings were rough and humble—in the 1830s, the region was a popular passage for travelers and merchants moving between the Great Lakes and the Mississippi River, and a few settlers decided to set up a small village on the icy banks of Lake Michigan. Over time, the village grew into the Midwest’s commerce and transportation hub, aided by the introduction of major railroads and the increased shipping traffic through the young city’s waterways—soon, it was recognized as a key centralized nexus between both eastern and western coasts of the nation. While mercantilism, trade, and shipping were streaming into Chicago, tiny enclaves of pioneers and farmers began to settle around the outskirts of the bustling commercial center—precursors to the mélange of Chicago neighborhoods that would later be embraced by the far-reaching city limits.
The city was forever changed by the Great Chicago Fire in 1871. The causes of the blaze remain a mystery—although local legend persists in blaming Mrs. O’Leary’s cow for kicking over a lantern—but the aftermath was indisputable: One-third of the existing city burned to the ground. The reconstruction that followed led to several new ideas about the city’s architecture and design, including the grid-like layout and tremendous amount of lakefront parkland. Despite the destruction of the city’s downtown, Chicagoans have an earned reputation for resilience, and as they rebuilt—primarily in brick and stone, instead of wood—they remade the very aesthetics of their city. Modern developers have sought to maintain and add their own spins to the traditional brownstone walkups and courtyard residential complexes that became the dominant housing in the post-Fire years.
During this period revolutionary architects and structural engineers such as Louis Sullivan; William Holabird and Martin Roche; Daniel Burnham; Mies van der Rohe; and Frank Lloyd Wright took advantage of the blank canvas left in Chicago’s ruined downtown. The world’s first skyscraper was erected in Chicago—although a mere ten stories tall, it represented a new way of thinking about urban buildings. Steel-frame high-rise towers were followed by stunning achievements in vertical construction, including what were for many years the world’s tallest buildings, including the famed Willis—once Sears—Tower. Of course, not all of Chicago’s buildings are record-setting monuments. High-rise condominiums may span the length of the shoreline north and south of downtown, but the rest of the city’s housing consists of mid- and low-rise buildings and one- and two-story homes.
Neighborhoods just north of the Loop—centered around the area south of where the Chicago River meets Lake Michigan—are characterized by tree-lined streets and rows of stately townhomes. The majority of these are divided into flats, but many have been maintained as single-family residences. Vintage courtyard condominiums and converted apartment buildings also line the blocks, while new construction and rehab projects continue to revive older structures, providing homebuyers with modern living spaces close to downtown. Northern Chicago neighborhoods along the water’s edge include Lincoln Park, Lakeview, Uptown, Edgewater, and East Rogers Park, all of which have the additional attraction of breathtaking lakefront parks, marinas, golf courses, and beaches.
Chicago’s south side has also developed into a trendy hotspot for first-time buyers and younger working-class residents due to the conversion of its industrial district into a collection of luxury lofts and new residential condominiums. While maintaining each area’s rich cultural history and landmark sites, developers and community organizations have renewed this once-dilapidated section into a thriving, desirable place to live. Long stretches of pristine parkland including extensive pedestrian and bike paths run along the shoreline connecting the South Loop, Douglas, Oakland, Kenwood, and Hyde Park neighborhoods to the Loop and beyond.
Detached single family homes, complete with yards and private garages, become more common the further one travels from the Loop and lake. Many of these Chicago neighborhoods matured from early townships and settlements established by European immigrants and pioneering individuals. Throughout the years these small communities were annexed into the city, becoming an official part within Chicago’s expanding borders. Influenced by strong cultural ties, each neighborhood holds a unique identity that adjusts with the changing times. While one is sure to find rows of tightly packed, classic Chicago bungalows in many of these far south, west, and north side areas, homebuyers will also discover large Victorian homes and more contemporary residential designs set on sprawling green lots.
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