Chicago's Cigar Scene
Chicago boasts one of America's richest cigar traditions, anchored by Iwan Ries & Co., the legendary tobacco shop that's been serving aficionados since 1857. The city offers everything from three-story historic shops in The Loop to modern lounges in the West Loop and River North. Award-winning suburban destinations like Blue Havana II in Naperville draw visitors from across the region with their exceptional selections and service.
What makes Chicago special is its blend of old-world tradition and contemporary sophistication. Family-owned institutions like Neisser's (since 1906) coexist with upscale modern lounges featuring craft cocktails and event spaces. The city's lounges serve diverse neighborhoods - from Lincoln Park locals to South Loop convention-goers to North Shore suburbanites. Despite harsh winters, Chicago's cigar culture thrives in comfortable indoor spaces perfect for year-round enjoyment.
Chicago City Lounges (8)
Cigar lounges located within Chicago city limits, from downtown powerhouses to neighborhood favorites across the city.
Iwan Ries & Co.
A Chicago institution since 1857, Iwan Ries is one of America's oldest tobacco shops. Three floors featuring a massive walk-in humidor, pipe museum, and smoking lounge. The premier destination for serious collectors with unmatched selection and history.
Casa de Montecristo
Upscale cigar lounge in the heart of River North. Premium selection, full bar, comfortable leather seating, and excellent ventilation. Part of the renowned national chain. Popular with business professionals and tourists.
Tesa Cigars
Lincoln Park's premier cigar destination featuring walk-in humidor, comfortable lounge, and neighborhood atmosphere. Great selection of premium brands, knowledgeable staff, and loyal local following.
Up Down Cigar
Modern cigar lounge in the trendy West Loop. Two-level space with contemporary design, full bar, and excellent ventilation. Popular with younger professionals and features regular events.
Nicki's Cigars
Family-owned cigar shop and lounge in Greektown. Comfortable atmosphere, good selection, and friendly service. Popular pre-game spot before Bulls and Blackhawks games at United Center.
Biggs Mansion
Historic Victorian mansion converted to private event space and cigar lounge. Elegant atmosphere, premium cigars, full bar, and beautiful architecture. Available for private events and special occasions.
Jenuwine Cigars
South Loop cigar lounge with comfortable seating, good selection, and neighborhood feel. Full bar, TVs for sports, and regular customer base. Convenient location near McCormick Place.
Eight Cigar Bar
Upscale cigar bar in River North area featuring premium cigars, craft cocktails, and modern atmosphere. Popular with downtown professionals for after-work gatherings and client entertainment.
Suburban Lounges (4)
Premium cigar destinations in Chicago's suburbs, offering excellent selections and often more relaxed atmospheres worth the drive.
Blue Havana II
Award-winning suburban cigar lounge named one of the best in America. Extensive humidor, full bar, comfortable seating, and welcoming atmosphere. Worth the drive from Chicago for the selection and service.
The Cigar King
North Shore favorite with massive walk-in humidor and comfortable lounge. Excellent selection of premium cigars, competitive prices, and knowledgeable staff. Worth the trip from Chicago.
Neisser's Smoke Shop
Charming suburban smoke shop with excellent cigar selection and small lounge. Family-owned since 1906, offering personalized service and quality products. A Northwest suburbs institution.
Tobacco Row
Northwest suburban cigar shop with walk-in humidor and small lounge area. Good selection of premium brands, friendly service, and convenient location. Popular with locals.
Cigar Shops (1)
Excellent cigar selections without dedicated lounges, perfect for picking up quality cigars at competitive prices.
Cheap Cigars
Don't let the name fool you - they carry premium brands alongside everyday smokes. Multiple Chicago locations, competitive prices, and decent walk-in humidors. Great for value-conscious buyers.
Chicago Cigar Tips
Best Times to Visit
Weekday afternoons (2-6pm) are ideal for browsing without crowds. Downtown spots get busy after work (6-9pm) with business crowds. Visit Iwan Ries on weekday mornings to explore all three floors at your leisure.
Neighborhoods to Explore
The Loop/River North for downtown convenience and upscale options. Lincoln Park/Old Town for neighborhood charm. Suburbs (Naperville, Skokie) for award-winning selections.
Chicago Cigar Culture
Iwan Ries is a must-visit for any serious aficionado - budget time to explore all three floors. Winter lounges provide warm respite from brutal cold. Consider Blue Havana II for a suburb day trip. Illinois taxes are high.