Up Down Cigar

Old Town has kept a cigar shop on Wells Street since 1963, and it was run for most of that time by one of the most important women in American tobacco.

Diana Silvius founded Up Down and made it a landmark — a nationally famous, pioneering female tobacconist in a trade that assumed she wouldn't be. She died in 2016 at 81, mourned in Cigar Aficionado as a legendary retailer; her successors keep the shop and her name's house line, the Dominican Diana Silvius blend, going. The current building, with its unmistakable cigar-store signage, has anchored the block since 1975.

The Patio

Here's the Chicago wrinkle: the indoor space is retail, and the lounge is out back — a heated, covered patio that runs year-round, where BYOB whiskey or wine alongside your smoke is simply how it's done. In a January cold snap, a warm patio and a good cigar is a very Chicago kind of defiance.

The Shop

Sixty-plus years of curation: every major cigar brand, a deep pipe and accessories wall, and the institutional memory of a store that has watched Old Town change around it and stayed exactly what it is.

Why We Picked It

Because a neighborhood institution with a genuine pioneer's legacy is worth the fourth chair even when its lounge is a patio and its website is having a bad year. Call ahead, bring a bottle, and smoke in the shadow of a Chicago legend.