Chireal Jordan: Building A Chicago Hospitality Empire

Imagine being the only Black general manager on Chicago’s entire north side. That was Chireal Jordan’s reality early in his career. It’s a challenging position that not only shaped his perspective but also fueled his ambition to build something truly his own. Today, Jordan is a co-founder of Machine Hospitality Group, a testament to his vision and resilience in one of America’s most competitive restaurant cities.

From Lone GM to Hospitality Mogul

Alongside his business partner Brian Galati, Jordan co-founded Machine Hospitality Group in 2012. For over a decade, they’ve been creating unique dining and drinking experiences in Chicago. Their portfolio includes popular spots like Headquarters Beercade and Machine Cocktail Bar in River North, and Dearly Beloved, a cocktail restaurant celebrated for its star drinks. And the expansion doesn’t stop there – a fourth location is set to open in Fulton Market this August.

The initial vision was simple yet powerful: create establishments that they themselves would be proud to own and excited to visit. This guiding principle has helped them navigate the complexities of the industry, transforming from their earlier name, Capacity Bar Group, into the more defined Machine Hospitality Group. The name ‘Machine’ perfectly captures how Jordan and Galati, despite their different approaches, function seamlessly as a unit.

Navigating a Tough Industry

Breaking into the hospitality industry wasn’t easy. Jordan learned the ropes in large bar and nightclub groups, often feeling like he was thrown into the deep end. The most valuable lessons weren’t about mixology or service, but about the drive to build his own success. ‘I could not handle making someone else rich when I felt that I knew more than my predecessors,’ he explains. The risk of striking out on his own felt more manageable than staying under someone else’s ceiling.

He quickly learned that success in this business hinges heavily on relationships, from the neighborhood level right up to the alderman. Each area operates differently, requiring a delicate touch to avoid jeopardizing opportunities. The leap to ownership brought a profound sense of humility. Jordan notes that the reality of submitting payroll, paying rent, and dealing with hidden taxes and fees keeps you grounded and focused on the fight.

The Power of Partnership and Vision

Jordan admits that he and Galati often disagree, but after 14 years, they’ve learned to harness these differences. ‘We always reach the same finality, however 99% of the time we offer differing paths,’ Jordan shares. He believes their contrasting instincts, combined with discipline, accountability, and laughter, make their partnership stronger. Crucially, their vision for the spaces they create has always been aligned. Jordan emphasizes his goal is to build inclusive environments where everyone feels comfortable, regardless of background.

Having spent 25 years in the industry, Jordan has witnessed significant changes, particularly in representation. He notes the encouraging increase in Black ownership across Chicago in recent years, moving beyond just pockets on the South Side. ‘It is fantastic to see and more importantly, to be a part of,’ he says. He understands the profound importance of representation, often receiving heartfelt sentiments from individuals who are inspired by his journey.

Looking Ahead

With national ambitions that were put on hold by the pandemic, Machine Hospitality Group is looking towards future expansion. Despite the company’s growth, Jordan’s core advice remains the same. He acknowledges Chicago’s challenging restaurant landscape, stating, ‘This city is not pro-restaurant.’ His enduring message? ‘Do it with your heart because there are no easy days, no weekends. But you can do this and you’re never alone.’