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There is no doubt that Chicago is the cultural and economic capital of the Midwest. With more than 2.7 million residents, it’s also the largest. “The Windy City” offers residents plenty to do between the roughly 7,300 restaurants, 600 parks, 250 live music venues, and nearly 40 annual parades. But all of these attractions are not stopping people from drifting toward another, more affordable city in the Midwest. A recent U-Haul study found that Gen Xers (those born between 1965 and 1980) and millennials (those born between 1981 and 1996) are relocating to Milwaukee, Wisconsin, which is just a 90-minute drive from Chicago.
In the U-Haul 2026 Midyear Migration Trends: Metros study, researchers analyzed one-way transactions by generation from every U.S. metro with at least 1 million residents. The data, collected between July 2025 and June 2026, examined net-gain destinations for each generation of U-Haul customers. Among those leaving Chicago, Milwaukee ranked as the No. 1 destination for Gen Xers and millennials…