Chicago Cigar Bar – Where to Smoke a Cigar in Chicago

Redhead Piano Bar

The Redhead Piano Bar

16 W. Ontario St | Near North Side
(between State and Dearborn)

Chicago’s premier piano and cigar bar. The Redhead hosts monthly cigar and whiskey pairing events in their large enclosed smoking patio. The patio is perfect for year round smoking. The Redhead also offers cigar lockers and a large walk in humidor.

Redhead Piano Bar - Cigar Membership Program

Prime & Provisions Logo

Prime & Provisions

222 N LaSalle St | The Loop

From the team that brought us Bar Siena, Siena Tavern and Public House comes Prime & Provisions. A River North steakhouse that has an outside patio that allows smoking. Prime & Provisions offers several cigars of different brands for sale.

BYOB Cigar Lounges

Biggs Mansion Chicago

Biggs Mansion

1150 N Dearborn St | Near North Side

Biggs Historic mansion built in 1874 and restored in 2014 offers an indoor and outdoor patio. Biggs Mansion also offers lockers, party spaces and special events. New member privileges include a humidified locker, the ability to BYOB, custom key for entrance, complimentary guests per visit, reserved patio seating, and exclusive discounts on full box and accessory purchases.

Iwan Ries Logo

Iwan Ries

19 S Wabash Ave 2nd Floor | The Loop

The oldest tobacco shop. Opened in 1857 Iwan Ries hosts cigar and whiskey pairing events. Iwan Ries offers 15,000 pipes and hundreds of cigars. Member benefits include discounts on purchases, guest passes, personalized key card access, exclusive tasting events and more.

Erie Cafe


Erie Cafe

536 W Erie St | River North

Located along the North Branch of the Chicago River on Erie Street, The Erie Café serves prime aged steaks, chops and house specialties in a classic club-like environment. Situated in the historic River North area, this architecturally significant building features arched stoned windows overlooking Chicago’s Loop. It was carefully rehabbed to become The Erie Café, a steakhouse that opened its doors in September, 1994. Erie Cafe allows smoking outside.


Chicago born and raised. Always looking for new places.

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