HERFIO GUIDE
Where to have a cigar and a cocktail in Chicago.
Chicago has a couple of especially clear choices when you want bar service and a cigar in the same stop.
THE SHORT VERSION
The strongest current options are hospitality-driven rather than traditional cigar shops: Redhead pairs its smoking patio with a full piano bar, while Prime & Provisions puts its cigar lounge next to a steakhouse and full bar.
The Redhead Piano Bar
River North
Full River North piano bar with cocktails, a heated smoking patio and its own walk-in humidor.
River North piano bar with a heated year-round smoking patio, custom walk-in humidor, full bar, live music and some of the latest cigar-friendly hours in the city.
Worth knowing: Smoking is outdoors.
See the full place profilePrime & Provisions
River North
Steakhouse and full bar paired with a heated covered outdoor cigar lounge.
River North steakhouse with a heated, covered outdoor cigar lounge, full bar and dinner service, making it one of Chicago’s clearest options for doing dinner, drinks and a cigar in one stop.
Worth knowing: Only two current Chicago places clearly qualify for this guide.
See the full place profileHow we made this list: Selections require current cigar-smoking access plus a real full bar or cocktail program. With only two clearly qualified places in the current data, this guide remains noindex until the city has more depth.
Editorial picks are separate from paid placement. Policies, hours, and cigar inventory can change, so the individual place pages show the underlying research and verification details.
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