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Evanston, IL
Evanston sits directly north of Chicago along Lake Michigan and is home to Northwestern University, whose lakefront campus and roughly 20,000 undergraduate and graduate students give the city a genuine college-town energy layered on top of its identity as a Chicago suburb — a combination that's produced a denser concentration of bookstores, theaters, and independent restaurants than most comparably sized suburbs. The city was also the founding headquarters of the Woman's Christian Temperance Union, and the Frances Willard House, preserved as a museum, commemorates Willard's leadership of the organization and its significant role in both the temperance and women's suffrage movements of the late 19th century — a genuine piece of national reform-movement history tied directly to the city. Evanston's public beaches along Lake Michigan give residents direct lakefront access rarely available in suburbs further from the shoreline, and both the CTA's Purple Line elevated train and Metra's Union Pacific North Line serve the city, putting downtown Chicago within roughly 25 to 35 minutes depending on the service and specific stop. In 2019, Evanston became one of the first cities in the United States to approve a reparations program funded specifically for Black residents affected by historical housing discrimination, a policy that drew national media attention and positioned the city as an early test case for how American municipalities might address the lasting effects of redlining and discriminatory zoning.
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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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