Little Chicago 

A slang term for Cleveland, OH.

Cleveland is nicknamed "Little Chicago" or "Lil Chicago" because of it's many similarities to Chicago, but everything is just on a smaller scale. The demographics and trends for both areas are very similar. Fads and styles that start in Cleveland will quickly spread to Chicago and vice versa since the cities are relatively close and very connected.

The nickname has been around since the early-mid 1900s when Cleveland was at one time the 5th largest city in the country and rivaled Chicago but was just slightly smaller. People started noticing the striking similarities between the two big cities. Cleveland also had a huge mafia presence like Chicago and the Cleveland and Chicago mafia families were allies for a long time.

Lets go to Little Chicago AKA Cleveland.

Little Chicago by LilChicagoCleveland September 1, 2009

Little Chicago 

Little Chicago refers to a city called Hamilton just North of Cincinnati in Ohio. It got its nickname in the 30’s due to Gangsters from Chicago building businesses and second homes in the city. Now a days when people say little Chicago they mainly refer to the East side of Hamilton which is over run with crime, Gang violence, and drugs. Where as the West side is often referred to as Hamiltucky.

Little Chicago is one of the last places I would want to live in Ohio, that and Cleveland.

Little Chicago by All things Ohio September 6, 2020

little chicago 

Hamilton, ohio In the 1920 Chicago gangsters made Hamilton, Ohio their second home. John Dillinger is documented to have been a visitor to Hamilton. During World War II, due to the large number of gambling and prostitution establishments such as Madame Freeze's and the long row of prostitution establishments along Wood Street (now called Pershing Ave), the entire city was declared off-limits to military personnel.
Hamilton is still known as little Chicago, although it is now just a drug infested shit hole, that some folks call home.

Screw Cincinnati, lets go to little Chicago, the crack rocks are bigger there.

little chicago by Ford Lawnmower October 18, 2007