National Master Vince Berry has a bright thought: we should compile a list of chess-friendly restaurants, cafés, and other businesses that give a home to casual chess. Chess happens in surprising places.
In the 1980s, Vince and I used to play at the legendary P-K4 barbershop across the street from Holy Name Cathedral, and Vince remembers a resale shop at Roscoe and Damen that supports casual play. You'd always find Rick Lang and the late Raj Yahya at Ennui (Lunt and Sheridan, in the same building as Papa Dee's Chicago Chess Club); it's closed now! Memories like these are nice, but tell us where you're playing chess now.
I go to Pressure Billiards & Cafe (6318 N. Clark) to study chess. It's not a chess hotbed, but it's chess-friendly. Sometimes a friend will be on ICC, and sometimes I'll get suckered into playing blitz risers.