Every recommendation here radiates from Halas Hall in Lake Forest, the Bears' year-round practice campus off Route 60, not from downtown Chicago or Soldier Field nearly an hour south. Lake Forest and its North Shore neighbors (Lake Bluff, Highwood, Highland Park) give a player a short, private commute and one of the most discreet, low-crime enclaves in the metro. The picks below prioritize privacy and a tight drive over the venue, so you live near where you work, not where you play on Sundays.
The most exclusive pocket of the North Shore: gated, tree-screened estates on bluffs above Lake Michigan, many designed by Howard Van Doren Shaw and David Adler.
A newer guard-gated enclave built around the Tom Fazio-designed Conway Farms Golf Club, with custom homes on quiet cul-de-sacs.
Large wooded parcels near Middlefork Savanna and Lake Forest Academy, blending newer construction with established estate lots.
A small, charming village just north of Lake Forest with a walkable center, beach access and a tight-knit, low-key community.
The neighborhoods above sit inside a twenty-minute drive of Halas Hall. 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.