Chicago
The Press Room
The Press Room is in the basement of a building on Washington Boulevard in the West Loop, a former Free Methodist Publishing House from 1891. There's a large green neon sign at street level that reads "Down for a Drink" with an arrow pointing down. Subtlety was apparently not the goal, but it works.
The space is dim with exposed blue brick and polished wood, and the drinks are well-priced for the neighborhood. Happy hour daily from 4 to 6pm drops the old fashioneds and martinis to $8 and includes $2 oysters. It's the kind of lower-level bar that earns repeat visits.