Chicago's Lakeview neighborhood has always been a popular spot, even back in the day when it was the site of a Native American footpath and camp for the Miami, Ottawa and Winnebago tribes who regularly traveled through the area. The first European settler in the region was Conrad Sulzer of Switzerland, but many other pioneers soon followed him, planting roots in the territory north of Chicago's bustling streets. The early settlement experienced its first major population boom after a cholera outbreak in Chicago in 1854. The epidemic prompted many Chicagoans to head north and take refuge at the Hotel Lake View, so named for of its spectacular view of Lake Michigan. Once folks saw what a scenic and peaceful place lay just a few miles north of the polluted and overcrowded city—a place that was also free of disease scares—many decided to stick around.

The Lake View civil township incorporated in 1857, with the Town Hall located at what is now the intersection of Halsted and Addison streets. At the time, though, there were few roads beyond the Indian trail (which was later paved and called Clark Street) that ran north and south, connecting the new town to Chicago. The owners of the Hotel Lake View actually built another north/south street, made out of wooden planks, which cut through the neighborhood where Broadway now exists. Starting in the early 1870s, the population of the Lakeview Township grew at an exponential rate, ballooning from just over a thousand people at the beginning of the decade to more than 50,000 by 1890. This unprecedented growth was due to the beauty of the area as well as the many jobs that were being created by the arrival of industry. A commercial district blossomed around the turn of the century at the intersection of Diversey Parkway and Clark Street which remained a popular marketplace throughout the years, eventually evolving into the Century Shopping Centre which stands at that spot to this day.

Today, Lakeview is composed of mostly low- and mid-rise condominiums and townhouse-style buildings, with brick walk-ups and brownstones lining the residential blocks. The neighborhood has a feeling of urban density in places, with a refreshing abundance of trees and variety of architectural nuances. Many of the structures were built during the housing boom of 1889, and over 40 percent of the existing buildings are from that time period. Houses have been ceaselessly rehabbed over the years, leaving some properties a little rough around the edges but still desirable places to live.

The atmosphere throughout Chicago's Lakeview neighborhood fluctuates greatly depending on where you are. The hushed residential avenues starkly contrast the bustle of the bar scene in Lakeview's happening entertainment district, where streets are well-lit and people are out and about at all hours. Residents say being able to live on a quiet street, while being within easy walking distance of so much shopping, nightlife, and dining options, is one of the biggest draws of the area.