[citation needed] In 1955, upon the first election of Mayor Daley, 43rd ward alderman Paddy Bauler, who kept a saloon in Old Town at North and Sedgwick Avenues called De Luxe Gardens,[20][21][22][23][24] famously declared "Chicago ain't ready for reform yet" many times over in his bar while dancing a jig.

This was mostly because by the 1950s and 1960s, many of the original families that had settled in the neighborhood had moved to the suburbs during white flight, leaving older Victorian buildings with storefronts available to rent inexpensively.

The Young Lords, then a street gang with Jose Cha-Cha Jimenez had a branch of their group at Wieland and North Avenues.

There is a little piece of Chicago Real Estate, west of Lincoln Park, that is the pride of urban conservationists and the despair of bulldozers.

I said we had no intention of marching on the Convention hall, that I didn't particularly think that politics in America could be changed by marches and rallies, that what we were presenting was an alternative life style, and we hoped that people of Chicago would come up, and mingle in Lincoln Park and see what we were about.The film The Weather Underground has a scene on La Salle Avenue in Old Town, which describes the Zeitgeist of the era.

Singer-songwriters such as Bob Gibson, Steve Goodman, Bonnie Koloc, and John Prine played at several clubs on Wells Street, such as The Earl of Old Town.

One large and successful folk club was Mother Blues, which featured nationally known artists and groups such as Jose Feliciano, Odetta, Oscar Brown Jr., Josh White, and Chad Mitchell.

In the early 2000s, this trend had begun to shift towards a gentrification of the area south of North Ave. on Sedgwick, Blackhawk, Hudson and Mohawk streets, near the Marshall Field Garden Apartments.

The area to the west of these streets, near the North and Clybourn Red Line stop had been dubbed "SoNo" by real estate developers.

Currently, Old Town south of North Avenue is a mixture of wealth and poverty, though the area is steadily gentrifying.

[31] The demolition of the Cabrini–Green high rise housing projects to the south has led to significant demographic changes in the neighborhood.

[39] In the 2010s, CPS considered merging Jenner K–8 in Cabrini-Green and Manierre together, but concerns involving students crossing gang territorial lines meant that both schools remained open.