Chicago's cigar story is the country's oldest: Iwan Ries has been trading on Wabash since 1857, the Biggs Mansion pours in an 1874 Gold Coast landmark, and Up Down Cigar has anchored Old Town for generations. Jazz history, architecture, and a proper winter lounge season, the family will feel at home.
Tap a gold pin to see the lounge and jump to its card below.
America's oldest family-run tobacconist, trading on Wabash Avenue since 1857, with a second-floor smoking lounge in an 1881 building.
Pip’s Tip Oldest family-run tobacconist in America, trading since 1857. The lounge is up on the second floor, not street level.
Private cigar club inside an 1874 Gold Coast mansion, fireplaces, leather and Gilded Age rooms. Day passes available; business casual.
Pip’s Tip Private club inside an 1874 Gold Coast mansion, so call before you count on getting in.
The Old Town institution on Wells Street, generations of Chicago smoke.
Pip’s Tip The Old Town institution on Wells Street, generations deep.
Chicagoland's flagship lounge, one of the biggest humidors in the Midwest.
Pip’s Tip Chicagoland's flagship lounge, one of the biggest humidors in the Midwest.
West suburbs' members-friendly den.
Pip’s Tip West suburbs' members-friendly den.
Private-club polish in River North.
Pip’s Tip Private-club polish in River North.
Chicago's own boutique brand, rolled and smoked on site.
Pip’s Tip Chicago's own boutique brand, rolled and smoked on site.
North Shore humidor with lounge chairs.
Pip’s Tip North Shore humidor with lounge chairs.
BBQ, comedy and cigars, Berwyn's gloriously weird institution.
Pip’s Tip BBQ, comedy and cigars, Berwyn's gloriously weird institution.
Northwest suburbs' old-school counter.
Pip’s Tip Northwest suburbs' old-school counter.
90 minutes north, Milwaukee's 1939 tobacco landmark.
Pip’s Tip 90 minutes north, Milwaukee's 1939 tobacco landmark.
An 1874 Gold Coast mansion turned cigar sanctuary, fireplaces, leather, and rooms that remember the Gilded Age. Day passes open the door; the experience keeps you coming back.
The family's first Chicago night, before the cold sets in.
Destination weekend & Wave 1 celebration. Travel packages for members.
Chicago is live, from an 1857 tobacconist to a Gilded Age mansion. The Midwest chapter starts here.