Route 66 traveled through Carlinville at the height of prohibition from 1926-1931. The infamous Ortic Inn was built on a farm several miles south of the city and purportedly used by gangster Al Capone and bootleggers running liquor from the south to Chicago.

Coal mining played a significant part of the economy of Carlinville. Standard Oil built 159 Sears and Roebuck kit homes in the city in 1918, and 156 still stand today.

Carlinville is famous for the Million Dollar Macoupin County Courthouse - one of the most extravagant courthouses in the country - and the Old Macoupin County Cannonball Jail - a slightly unorthodox prison allegedly structured with Civil War cannon balls in the walls to hinder escapees.