Biggs Mansion Chicago — Attraction in Chicago

The gentleman in the $3,200 Brunello Cucinelli cashmere hoodie is explaining cryptocurrency mining to a federal judge wearing what appears to be a vintage Hermès tie and Golden Goose sneakers. Between them, $180 worth of Dominican tobacco smolders in Baccarat crystal ashtrays, while a 70-inch Samsung displays the Bears game to an audience that collectively represents several hundred million dollars in net worth.

Welcome to Biggs Mansion, where Chicago's power elite has quietly revolutionized the luxury club experience by embracing what fashion insiders call "stealth wealth"—and what cigar aficionados simply call heaven.

Gone are the days when exclusive clubs demanded navy blazers and regimental ties. At Biggs, the annual membership fee ($5,145) buys entry to perhaps America's most sartorially democratic luxury space, where a software entrepreneur's $400 Off-White hoodie commands the same respect as a real estate mogul's $8,000 Kiton suit.

"The old rules don't apply anymore," says Marcus Chen, a 34-year-old venture capitalist who favors Rick Owens leather jackets with his Patek Philippe Nautilus. "Nobody cares if you're wearing Supreme or Savile Row, as long as you appreciate a good Padrón."

Members routinely mix high and low with seasoned stylist confidence: $1,200 Balenciaga Track sneakers with vintage Levi's, or $15,000 Hermès Birkin bags set casually beside $40 hoodies from local Chicago streetwear brands. This aesthetic democracy reflects broader luxury evolution—where previous generations signaled status through obvious displays, today's wealthy prefer "conspicuous inconspicuousness."

At this restored 1874 mansion, authenticity trumps ostentation. Members bond over niche brands—Japanese denim, Italian leather goods, small-batch American accessories—creating connections that transcend traditional networking. On recent evenings, the $50,000 Persian rug-anchored lounges hosted African American tech executives, Latino restaurant owners, white private equity partners, and Asian real estate developers, united by premium tobacco appreciation.

Day passes ($85) provide fascinating anthropological theater. Unlike members who move with proprietary confidence, day-pass holders exhibit "aspirational anxiety"—over-tipping staff, name-dropping connections, photographing everything except other patrons. Their fashion skews obviously expensive: conspicuous Gucci belts and Louis Vuitton accessories versus members' relaxed luxury aesthetic.

"The people trying hardest to look wealthy usually aren't," observes longtime member David Rodriguez, whose typical uniform consists of well-worn jeans, vintage band t-shirts, and a $40,000 Richard Mille watch. "Real money dresses for comfort, not cameras."

The cigar ritual demands particular sartorial considerations. Fabrics must withstand smoke without retaining odors, colors should complement tobacco's earthy palette, and accessories must accommodate holding cigars and cutting tools. These constraints evolved into aesthetic philosophy where form follows function, but function can be beautiful.

Whether Biggs represents sustainable luxury evolution or Chicago-specific anomaly remains unclear. Yet it demonstrates how luxury experiences can embrace diversity—economic, racial, aesthetic—without sacrificing exclusivity. The club attracts style-conscious elite who appreciate both $300 hoodies and $3,000 suits, where conversation flows like premium bourbon and the only dress code is good taste.

Member philosophy proves elegantly simple: "Smoke what you love, wear what you want, respect everyone." In an era of increasing social stratification, perhaps that's the most luxurious...

Firstly, I love this place. I've been coming for about the last 3 years (I took a one year break being out of the country) and I can't say enough positive things about my experience. The staff is amazing and SO knowledgeable about the brands and options that they have. They are also always restocking the tons of brands they have on hand in the huge humidor.

Speaking of staff, Karen, Gabby, Britt, Josey, Ruben and crew are so welcoming. They` greet the members and non-member regulars by name and always engage and chat like we're all old friends. Karen, one of the staff started the first day that I was a member there, and she is the one that made my deciding factor to join. She toured me through the mansion, gave me a rundown of the benefits and introduced me to the rest of the staff on duty, all on her first day of work! She was very pleasant, friendly, and engaging every time I arrive.

Apart from the vast cigar options,I highly recommend Biggs Mansion for the warm clientele of all walks, the incredibly friendly, pleasant, and welcoming staff, and for the great location near tons of great mature bars and restaurants.

Bottom line: Go to this place. If cigars and atmosphere are your thing, you will...

Stopped in to pick up a few cigars & enjoy an after dinner smoke around 8:30p. After choosing the smokes, curing & lighting up & leaving a good gratuity, there were not any seats inside. We went outside to a nearly empty patio. A staff person outside then starts pointing to a sign. It was dark & I told him that I couldn’t read it. Instead of saying something like “I’d sorry sir but the outside is reserved for members”, he makes me walk over to the sign to read it. We did not realize the outside was reserved for Members. He then says that I can pay $100 to sit outside. So, let me get this str8, I supposed to pay $100 to enjoy $30 of cigars on an empty patio? OK, I get that there is a Membera Only section….then kindly explain the situation. Don’t just point to a sign in the dark with condescending rudeness. Been in Chicago 2 weeks and by far the worst service that we have...