The Loop · Gold Coast · Old Town · Chicago, Illinois
Illinois law lets a cigar room smoke or pour — never both — so every great lounge here is BYOB, glasses and ice on the house. What Chicago trades in liquor licenses it more than repays in heritage: the oldest family tobacconist in America, a Gold Coast mansion, and rooms grandfathered before the rest went dark.
Editor's Pick · No. 1
The Loop · Chicago, IL · ★4.8
Founded in 1857 and run today by the fifth generation of the same family — the oldest family-owned tobacconist in the country, two blocks off Michigan Avenue. The Front Room upstairs is 2,500 square feet of original mahogany and crystal chandeliers, open to midnight on weekends, grandfathered when nearly every other downtown smoking room went dark in 2008.
The Gold Coast to the South Side
An 1874 mansion three years newer than the Great Fire — working fireplaces, billiards tables, three hundred engraved lockers, and a free walk-in lounge behind the private-club doors.
Eight thousand square feet — the region's biggest — with a computer-controlled aging room, a private-elevator VIP floor, and a national-caliber event calendar.
Sixty years on Wells Street, founded by the legendary Diana Silvius — one of America's pioneering women tobacconists — with a heated, covered BYOB patio out back.
The Northwest Side's near-perfect room: a giant walk-in humidor, exclusive Don V house blends by Oscar Valladares, and a members' lounge open around the clock.
Bronzeville's living room: Black-owned since 2018, BYOB with live music and karaoke, and the latest-running hours on this list. The anchor of the South Side scene.