Biggs Mansion

Three years after the Great Fire took the city down, a Northern Trust co-founder built this house back up in stone. A century and a half later, you can smoke a cigar by its fireplaces.

Banker John DeKoven raised the mansion in 1874 to a design by architect Edward Burling, and died in it in 1898. In 1964 the society caterer Joseph Biggs turned it into a restaurant famous for waiters who recited the menu from memory; a $4-million, two-year restoration reopened it as a cigar club in September 2014. Few rooms in America come with this much building attached.

The Room

Working fireplaces, leather couches, two American Heritage billiards tables, and some three hundred humidor lockers with brass engraving, all under the double ventilation that keeps a hundred-fifty-year-old house breathing. The upper floors are members'; the ground-floor walk-in lounge is genuinely free, which makes the private-club branding friendlier than it sounds.

The Humidor

Davidoff, Fuente, Padrón — a Gold Coast selection for a Gold Coast address. Come for a cigar and a game of billiards by the fire; it's the most complete room in Chicago smoke, and it knows it.

The Pour

BYOB by Illinois law, and Biggs leans into it — staff pour your bottle, restaurant delivery is encouraged, and the good wine you bring is the whole point. Bring something worthy of the mantelpiece it'll sit on.

Why We Picked It

Because atmosphere is half of everything this site rates, and no room in the city has more of it than a restored 1874 mansion with a fire going. Iwan Ries is the heritage; Biggs is the evening.