4914 N Milwaukee Ave, Chicago, IL 60630
The Gale Street Inn that I’ve always known sat on the corner of Milwaukee Ave. and Gale St. It’s fancy structure with hanging roofs, and dark green siding never indicated a historical significance in my mind. But I added it to my field guide because of its close proximity to the transit center, the most historically significant location on this map. I inferred that it had to have some historical context if it was so close to what was once the Wentworth Inn, and it did!
The original Gale Street Inn was established in a tavern (that no longer exists) across the street. It no longer exists because it was torn down to make room for the transit center! In 1963 the restaurant was owned and opened by George and Joan Chioles. It was a successful business from the start thanks to their famous ribs. They brought in a significant amount of business in their tavern for about six years until the city forced them to shut down so that they could tear down the building and create the transit center. The couple didn’t want to leave that location, especially given the influx of people the transit center would bring so they purchased the building directly across the street and continued business as usual. In 1985 they sold the building to new owners but the success of the restaurant still continued.

Given the historical development of the transit system, this restaurant that was once only truly appreciated and known to locals was now a Chicago staple. Commuters from the city and the suburbs who traveled through the Jefferson Park transit system were now introduced to the hidden gem on the corner, creating a larger network of customers and more exposure of the neighborhood itself to outsiders. This indirectly contributed to the population growth of the neighborhood.
In the built environment today, the transit system directly across the street has grown immensely. This growth means a larger population of people are coming into Jefferson Park than ever before. Today, on a friday night, it is unlikely that you can order a slab of ribs past seven pm because they’re sold out by then. The customers and demand brought by the surrounding system of transportation continues to contribute to this restaurant. In addition, other businesses have followed in Gale Street Inn’s example and are taking advantage of the fantastic location. I mentioned Weston’s in our walk through the transit center but that is truly the first establishment since Gale Street that has brought a business that truly caters to the population around them; commuters.
Given the more recent establishment of Gale Street Inn compared to other buildings on this guide, there isn’t necessarily a remake of this building or environment occurring. There is a slight shift happening in the types of businesses being built in that section of Milwaukee Ave. Again, the transportation hub has the largest impact on the community. Given the exposure it’s given Jefferson Park to a variety of individuals and the neighborhoods close proximity to the city, I predict that the area is one of the next “up and coming neighborhoods” in Chicago. The community itself is very middle class as a whole but I believe that it still has the potential to become gentrified in the next decade. Milwaukee Ave. spreads through the Logan Square and Wicker Park neighborhoods, both of which have been gentrified in the past twenty years. Jefferson Park is just a few miles north of these neighborhoods. The easy transportation, nice housing, close proximity to downtown Chicago and somewhat cheap real estate, makes this neighorhood the perfect target.
