Millennials And Gen Xers Are Leaving Chicago And Moving To Another Big Midwestern City

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. 

In addition to U-Haul's findings, a poll of 1,000 registered Illinois voters conducted by the Paul Simon Public Policy Institute at Southern Illinois University found 47% of all respondents said they wanted to leave Illinois. More than half of Gen Xers and millennials said they would like to move, and of all those who wanted to relocate, they cited high taxes as the top reason (27%). Milwaukee seems like a no-brainer for Gen Xers and millennials leaving Chicago. These two sister cities on the Great Lakes share many similarities, but where they differ is cost.

One draw for relocating to Milwaukee is the cost of living. According to Redfin's Cost of Living Comparison, housing cost in Milwaukee is 28% lower than in Chicago. The differences don't stop there. Lifestyle costs are also 14% lower in Milwaukee. For Gen Xers and millennials relocating from Chicago, this means a little more money in their pockets to enjoy what Brew City has to offer. Milwaukee has more than 100 festivals, more than 50 city parks, and nearly 40 breweries. It's also emerging as a culinary capital of the Midwest. Another win for Gen Xers and millennials planning to relocate to Milwaukee is that dining out costs 13% less than in Chicago. 

Like Chicago, Milwaukee is a waterfront city on Lake Michigan, so those relocating can still expect plenty of water recreation. Milwaukee has several lakefront parks for people to enjoy. Lakeshore State Park is Wisconsin's only urban state park and Lake Park, a beloved landmark since the late 1800s, features stunning panoramic views of Lake Michigan. It's also home to North Point Lighthouse, a historic landmark that symbolizes Milwaukee's maritime history. Residents can take in beautiful waterfront views, kayak on the lagoon, or bike the paved paths for cheaper prices. At the time of writing, in Milwaukee, kayak rentals start at roughly $18 per hour compared to $25 per hour in Chicago. Bike rentals start at $14 per hour in Milwaukee and $20 per hour in Chicago.

While Chicago is known for large outdoor music festivals such as Lollapalooza, Gen Xers and millennials won't miss a beat in Milwaukee, known as the Midwest's 'City of Festivals.' The city's Summerfest boasts 600 performers over nine days and is actually America's largest music festival. It's also cheaper than Lollapalooza. A one-day general admissions started at $30 for summer 2026, according to the Milwaukee Journal Sentinel, while a one-day general admission for Lollapalooza started at $185 for the same year on Festival Viewer.