Open and thriving since 1907, the Green Mill Cocktail Lounge survived both prohibition and ownership by Al Capone in the 20’s. That alone should make you want to visit.
Additionally, the plush restored interior hearkens back to its speakeasy roots with Grecian marble statues and art nouveau paintings in gilt scrolled frames. Live music plays 7 nights a week, there’s a free comedy show on Saturday afternoons called Paper Machete and you can stay for after hours shows between midnight and 5am on the weekends.
The Green Mill is one of Chicago’s best live music venues but they’re serious about their music; so, go for the atmosphere and save the conversation for later.