Windy City Cigar Lounge

Bronzeville has been a capital of Black cultural life in Chicago for a century. Since 2018, it has had a cigar lounge to match — and it runs later than anything else on this list.

Anthony Powell and Maurice Green opened Windy City in the heart of the historic South Side neighborhood and built it into what the Chicago Defender, marking its seventh anniversary, called a home away from home. It's the anchor of the South Side cigar scene, and it feels less like a shop than a living room that happens to sell cigars.

The Hang

Live music, karaoke nights, game-day viewings, and an outdoor patio — programming built for staying, not stopping. The weekend hours tell the story: open to 1 a.m. Friday and Saturday, the most "settle in for the night" schedule in Chicago smoke.

The Room

A boutique lounge, BYOB by Illinois rule, with a two-cigar entry that keeps it a room for smokers rather than a bar that tolerates them. What it lacks in humidor scale against the Loop giants, it more than returns in warmth and community.

Why We Picked It

Because a directory that only listed marble and mahogany would be lying about where cigar culture actually lives. Windy City is the neighborhood room done right — real people, real music, real late nights — and Bronzeville is exactly where Smoke & Settle wants to be.