West Loop
$500K-$6M+ (luxury new-build penthouses)Chicago's best-performing luxury market over the past decade: converted lofts, glassy new towers, and Randolph Restaurant Row, anchored by Google and McDonald's HQs.
Every recommendation radiates from the Advocate Center at 15 S Wood St on Chicago's Near West Side, the Bulls' training home in the Illinois Medical District just east of the United Center, not the Loop or Mag Mile. For a player, the practical center of gravity is the West Loop and Fulton Market, a five-to-ten-minute drive northeast, where the dining, recovery, and luxury rentals cluster.
Chicago's best-performing luxury market over the past decade: converted lofts, glassy new towers, and Randolph Restaurant Row, anchored by Google and McDonald's HQs.
The former meatpacking district turned dining-and-design destination, with full-floor penthouses and white-glove towers stacked above the restaurants.
A calmer pocket of riverside condos and townhomes between the West Loop and River North, less foot traffic and more residential than its flashier neighbors.
Chicago's most prestigious enclave: lakefront mansions, gilded co-ops, and Michigan Avenue at the doorstep, the highest-end address in the city.
The neighborhoods above sit inside a twenty-minute drive of Advocate Center. But many athletes prioritize lifestyle, privacy, and prestige over commute — these are the areas across Chicago where athletes most often buy and rent, even though they’re a longer drive from the facility.
The North Shore's old-money capital, with gated multi-acre estates set among ravines and bluffs along Lake Michigan. Elite private and public schools (Lake Forest Academy, Woodlands) and a discreet, deeply established community of executives and athletes.
Two of the wealthiest villages in Illinois, with tree-lined streets, lakefront mansions, and the nationally ranked New Trier school district. Jay Cutler and Bears head coaches have rented and bought here; lakefront homes routinely clear $4M.
Leafy, secluded lakefront suburbs where privacy comes from large wooded lots rather than guard gates — Michael Jordan built his famous fenced-and-gated 7.4-acre '23' estate in Highland Park. Strong schools and an arts-and-culture pedigree.
The marquee western-suburban alternative to the North Shore, with turn-of-the-century mansions in Hinsdale and newer gated estate enclaves in Burr Ridge. Nationally ranked District 86 schools and a polished walkable downtown.