The beautiful street in Chicago that was chosen among the “coolest” streets in the world

the Roscoe Street Shows between additional amazing From the worldaccording to the magazine time outWhich placed it in 28th place in its annual rankings. It was described as a prestigious magazine Roscoe Village neighborhood in Chicago As an area with independent businesses, family restaurants and a strong neighborhood community.

time out Highlight that Roscoe Street reflects A Active community With a strong presence of small businesses. The street brings together bars, shops and bakeries that build a distinctive local identity, according to the magazine.

Bars, shops and bakeries stand out on Roscoe StreetRetro Facebook on Roscoe

In the northern summer, This street receives Retro on RoscoeIt is a six-building festival featuring classic cars, antique vendors and outdoor activities. In 2025, it was held from September 5 to 7.

During the rest of the year, the street provides the opportunity to spend an entire day in between Shops, cafes and restaurants. Among the mandatory stops for visitors Shangri-La Vintage, El Tapatio Café and Volo BarFamous for its $1 limoncello and oyster drinks.

Roscoe Street is the axis around which the Roscoe Village neighborhood was born and transformedas detailed on the site Roscoe Village neighbors. Its history begins at the end of the nineteenth century, when it was developed Riverview Park He promoted the opening of businesses in Roscoe, Belmont and Western to serve thousands of visitors.

That movement strengthened and attracted the region working families, Mostly German AmericansThat fueled the first boom around 1920, when old greenhouses gave way to homes and brick buildings.

The street is characterized by its active community, small businesses, and strong neighborhood identityRetro Facebook on Roscoe

The growth of the region was not linear. Its first major pause came with the Great Depression, which marked the beginning of a long-term decline. Added to this was the post-war exodus from the suburbs, which left homes abandoned and property prices plummeting.

Only in the 1970s did a recovery beginwas promoted by a group of neighbors who founded Riverview Neighbors to confront insecurity and rebuild the fabric of the community.

Since then, Roscoe Street is starting to take on new lifeThis was thanks in large part to the arrival of the so-called “urban pioneers,” who purchased the two model apartments in Chicago with the intention of restoring them.

These projects marked a before and after in the neighborhood. Among them, the conversion of the Eversharp Building, known as the “Pencil Factory” in 1990, helped restore the neighborhood’s appeal.

List Street evaluation with various proposals Which allows you to do more than just a simple walk. time out I noticed Gastronomic projects Modern and creative spaces Cultural activitiesbut also the daily pulse of each neighborhood: those places where vinyl listening bars coexist with brick-and-mortar stores or century-old bars.

Roscoe’s Retro Fest turns six blocks into a corridor of classic cars, antiques and summer activitiesRetro Facebook on Roscoe

To compile the ranking, the magazine It asked its global network of editors and local professionals to choose the street that best represents their city They then ranked them according to different criteria: quality of food and drink, cultural offerings, entertainment options and, above all, sense of community.