Find cigars in Chicago.

Hyde Park

Hyde Park wine and spirits shop with cigars available in-store, useful when you want to pick up a few sticks alongside beer, wine or liquor rather than make a separate cigar-shop stop.

Cigar Lounge · Lakeview

Lakeview cigar and tobacco shop with a strong cigar selection, late hours and a small smoking/lounge area, making it a useful North Side stop when you want both retail and somewhere to light up.

Smoke Shop · Wicker Park

Wicker Park tobacco shop with a dedicated cigar section, late-night weekend hours and a broader smoke-shop selection; a practical cigar pickup when you are already around Division Street.

Cigar Lounge · Auburn Gresham

Auburn Gresham cigar business built around Bernard Terrell house blends and a premium-cigar focus, with more emphasis on its own cigar line than a broad national-brand catalog.

Cigar Lounge · Gold Coast

Gold Coast cigar shop and lounge inside the historic Biggs Mansion, with indoor smoking, a members patio and limited day-pass access for nonmembers; alcohol is not served.

Smoke Shop · Garfield Ridge

Garfield Ridge smoke shop with a premium-cigar offering, better suited to a quick retail stop than a destination cigar-lounge visit.

Cigar Shop · Ravenswood

Ravenswood cigar shop now operating on Wilson Avenue, with cigar-first retail but no smoking lounge at this location.

Cigar Shop · Wicker Park / West Town

Old-school North Avenue cigar shop with imported cigars, tobacco, accessories and an eccentric antique-filled interior; more of a browse-and-buy stop than a polished lounge experience.

Cigar Lounge · Fulton Market

Fulton Market cigar shop and lounge with public retail seating plus a members-only lounge and deck; limited day passes are available, but outside cigars, food and alcohol are not allowed in the public retail lounge.

Cigar Shop · West Loop

West Loop cigar and smoke shop with late-night weekend hours, a broad cigar selection and an on-site smoking setup; useful when you want a cigar stop that stays open well after traditional tobacconists close.

Cigar Shop · Greektown / West Loop

Greektown cigar retailer on Halsted Street with a long-running tobacco license and current specialty-retail presence; best treated as a straightforward cigar-shopping stop while lounge and brand details remain limited.

Edgebrook

Edgebrook smoking lounge with cigar sales, hookah and karaoke; indoor smoking and alcohol service are part of the setup, but the public cigar brand list is still thin.

Cigar Shop · River North

River North cigar shop with indoor smoking, a walk-in humidor and a small premium-brand mix, making it a practical downtown shop-and-smoke option.

Cigar Shop · Hyde Park

Hyde Park cigar retailer for neighborhood pickup and everyday cigar shopping; current smoking-lounge details are less clear than the retail side.

Cigar Shop · Loop

Historic Loop tobacconist with one of Chicago’s deepest cigar catalogs and a BYOB indoor lounge that offers day passes and stays open later than the retail shop.

Cigar Shop · Loop

Loop cigar specialist with a broad premium catalog, including major luxury and boutique names; best suited to serious cigar shopping rather than a lounge-first visit.

Smoke Shop · Portage Park

Portage Park smoke shop that carries cigars alongside a broader tobacco and smoke-shop assortment, making it more of a convenience retail stop than a cigar destination.

Smoke Shop · Armour Square

Armour Square cigar and vape shop with late-evening hours, useful for cigar pickup when you are near the South Side or Chinatown area.

Cigar Lounge · Jeffery Manor

Jeffery Manor cigar lounge with indoor smoking, outdoor patio seating, BYOB, humidified storage and a premium-cigar focus; built more for sitting down than making a quick retail stop.

Cigar Lounge · Norwood Park

Norwood Park cigar lounge and shop with indoor smoking, a walk-in humidor, premium and boutique cigars, plus an exclusive Don V house line.

Restaurant · River North

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.

Cigar Shop · Little Italy

Little Italy cigar shop and lounge with one of the city’s deepest brand lists, house cigars, aged and vintage inventory, and indoor smoking.

Smoke Shop · Uptown / Lakeview

Lakeview-area smoke shop with a walk-in humidor and premium cigar selection, useful when you want broad retail hours without needing a dedicated lounge.

Smoke Shop · Logan Square

Logan Square smoke shop with a premium-cigar selection and late retail hours, better for shopping than a sit-down cigar experience.

Smoke Shop · Bucktown / Logan Square

Bucktown/Logan Square smoke shop with a current premium-cigar collection including several major brands, making it a useful neighborhood retail stop.

Cigar Lounge · Beverly

Beverly cigar shop and lounge with long retail hours and a cigar-first identity; the public brand and amenity detail is still lighter than at Chicago’s better-known lounge stops.

Smoke Shop · Lakeview

Lakeview smoke and tobacco shop with cigars alongside hookah, glass and vape products, plus late weekend hours near the Wrigleyville nightlife corridor.

Smoke Shop · Lakeview

Lakeview smoke shop with cigar sales and long daily hours, useful for straightforward neighborhood pickup rather than a lounge-focused visit.

Smoke Shop · River North

River North smoke shop with cigar sales and very late weekend hours, most useful as a downtown retail stop when other cigar shops have already closed.

Cigar Lounge · Roseland

Roseland cigar lounge with indoor smoking, an outdoor patio and a premium-cigar focus, offering a public South Side lounge option without a membership requirement.

Cigar Lounge · Fulton River District

Fulton River District cigar shop and indoor smoking lounge with several premium brands; alcohol is not served, so the focus stays on cigars and the lounge itself.

Bar · River North

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.

Cigar Lounge · Austin

Austin neighborhood cigar shop and lounge with coffee, indoor smoking and outdoor seating, built more like a relaxed community hangout than a formal members club.

Cigar Shop · Edgebrook

Edgebrook cigar and tobacco shop with a premium-cigar focus, best for straightforward retail shopping rather than an extended lounge visit.

Smoke Shop · Near North Side

Near North Side smoke shop with cigar sales and a dedicated cigar room, useful for downtown-area pickup when you want broader hours than a traditional tobacconist.

Streeterville

Streeterville wine and spirits shop with a surprisingly deep cigar catalog, useful for pairing cigar pickup with wine, whiskey or other bottle shopping.

Cigar Shop · Old Town

Old Town cigar shop with premium brands and evening hours, a convenient neighborhood stop when shopping matters more than lounge amenities.

Smoke Shop · West Englewood

West Englewood smoke shop carrying cigars alongside vape and hookah products, best treated as a broad tobacco retailer rather than a cigar-first destination.

Cigar Lounge · Washington Heights

Washington Heights cigar shop and indoor lounge with late Friday and Saturday hours, giving the Far South Side a true sit-down cigar option after typical retail shops close.

Cigar Lounge · Bronzeville

Bronzeville cigar lounge with indoor smoking and late-week hours, a neighborhood lounge option on the South Side with a smaller public brand footprint.