O’Donovan’s (2100 W Irving Park Rd, 773-478-2100) When it operated as Schulien’s in the ’30s, this basement speakeasy employed a house magician. (The speakeasy is gone, but the magician remains to this day.)
Club Lucky (1824 W Wabansia Ave, 773-227-2300) Prior to becoming a restaurant, this building was a hardware store with a huge, pine-paneled speakeasy in the basement.
Halligan (2274 N Lincoln Ave, 773-472-7940) This bar’s speakeasy lore stems from access panels in the basement that lead to a secret tunnel running under Lincoln Avenue.
Southport Lanes (3325 N Southport Ave, 773-472-6600) When Prohibition was enacted, this tavern turned itself into a bowling alley—but kept a separate speakeasy and brothel upstairs.
Emmit’s (495 N Milwaukee Ave, 312-563-9631) Before becoming a bar, this building was a bank—one rumored to have had a brothel and speakeasy in the basement, complete with escape tunnels.
Jake’s Pub (2932 N Clark St, 773-248-3318) During Prohibition, Jake Rosenbloom owned this space that sold candy and sandwiches, but the back room served something a little stronger.
Lottie’s (1925 W Cortland St, 773-489-0738) This grocery store, called Zagorski’s back in the day, served up drinks and striptease acts in the basement during Prohibition.