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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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Naperville, IL
Naperville, spanning parts of DuPage and Will Counties roughly 30 miles west of downtown Chicago, has grown from a small early-19th-century settlement into one of the largest suburbs in the entire Chicago metropolitan area, with a population well over 140,000 — larger than many standalone American cities, let alone typical commuter suburbs. The Naperville Riverwalk, a landscaped pedestrian path built along the DuPage River beginning in the 1980s as part of the city's sesquicentennial celebration, transformed a formerly industrial stretch of riverfront into one of the most-used public gathering spaces in the western suburbs, hosting festivals, farmers markets, and a popular annual Ribfest event. Naperville's public school districts have consistently ranked among the strongest in Illinois, and the city has repeatedly landed on national "best places to live" rankings from outlets like Money magazine over the past several decades, a track record that's helped sustain steady population and housing-value growth even as some other Chicago-area suburbs have seen slower growth. Metra's BNSF Line connects Naperville to Chicago's Union Station in roughly 35 to 45 minutes, and the city's combination of a large, well-resourced tax base, a genuinely landscaped downtown riverfront, and consistently top-ranked schools has made it one of the most nationally recognized suburb names in the entire Midwest.
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