3 bars, restaurants, clubs, and venues open after 5. Hours, phone numbers, and vibes included.
An iconic, long-standing South Side staple. Grown, sexy, and incredibly lively neighborhood music lounge known for its amazing drinks, stepping music, and a warm local crowd celebrating Sunday night.
The New Apartment Lounge in Greater Grand Crossing hasn’t changed since 1980—same dim lighting, same soulful jazz, same Tuesday night saxophone rituals that drew Von Freeman and his crew. Skip the tourist traps; this South Side gem feels like stepping into a living history lesson, where the music’s older than the neighborhood itself.
# The Northcott Liquorette Duck into this speakeasy in downtown Naperville and you're stepping into a legit Prohibition fantasy—absinthe fountains, boozy teapots, and a whiskey collection that'll make collectors weep. The intimate setup moves fast, so lock in your reservation or risk getting shut out. Come thirsty and ready to play along with the old-school cocktail theater.