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Hinsdale, IL
Hinsdale sits in DuPage County roughly 17 miles west of downtown Chicago, and its downtown business district and residential streets retain a substantial stock of large late-19th and early-20th-century homes, a legacy of the village's early development as a retreat for wealthy Chicago business families following the city's rapid post-Great Fire growth in the 1870s and '80s. The village's historic train station, built in 1874 and still in active use, anchors a walkable downtown of independent shops and restaurants that's stayed largely free of the big-box and chain-heavy commercial development found in some larger neighboring suburbs. Metra's BNSF Line connects Hinsdale to Chicago's Union Station in roughly 30 minutes, a genuinely fast commute for a suburb of Hinsdale's size and one that's helped sustain consistently high demand for the village's larger, older housing stock even as new construction has driven prices further upward in recent years. Hinsdale Central High School has built a strong reputation for both academics and athletics within Illinois, and that reputation, combined with the village's historic housing stock and fast direct rail commute, has kept Hinsdale one of the more consistently expensive and sought-after western suburbs in the entire Chicago metropolitan area.
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Lake Forest, IL
Lake Forest sits on bluffs above Lake Michigan roughly 30 miles north of Chicago, and its Market Square, completed in 1916, is widely credited by architectural historians as one of the first planned shopping centers built anywhere in the United States — a deliberately designed commercial plaza built to serve the surrounding residential estates rather than growing organically along an existing street grid. The city's history as a retreat for wealthy Chicago industrial and business families dates back to its founding in 1857 by Presbyterian church leaders seeking to establish a college town removed from the city, and Lake Forest College, still operating today, traces its own roots directly to that founding mission. Large lakefront and near-lakefront estates, many dating to the late 19th and early 20th centuries and set well back from the road on heavily wooded lots, have kept much of Lake Forest's residential character oriented around privacy and scale in a way that's distinct even from other wealthy North Shore communities closer to Chicago. Metra's Union Pacific North Line serves Lake Forest with a commute of roughly an hour into downtown Chicago, a longer ride than closer-in North Shore suburbs like Wilmette or Evanston, reflecting the city's position further up the shoreline — a trade-off many residents have historically accepted in exchange for larger lots, mature wooded landscaping, and a genuinely historic planned commercial center in Market Square.
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