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Retirement doesn’t necessarily have to mean packing up for the Sun Belt. For some baby boomers, the next chapter might be just across the state line — somewhere they can enjoy a change of pace without straying too far from the people and places they know. That’s apparently the approach of many Chicago boomers, according to a U-Haul migration study: Wisconsin was the top net-gain state for baby boomers moving out of Chicago in mid-2026. For boomers looking to downsize, slow down, or find a city that’s a little more affordable, Wisconsin has some options. It has thousands of lakes and miles of scenic trails, alongside cities like Madison and Eau Claire, where award-winning breweries, museums, and senior centers can keep daily life exciting.
For its 2026 Midyear Migration Trends report, U-Haul looked at moving data from July 2025 through June 2026 to identify top net-gain destinations from major U.S. metropolitan areas. It then broke down those trends by generation. Wisconsin came in first for baby boomers (born between 1946 and 1964) leaving Chicago, followed by Florida and Michigan. While some Chicago boomers are following the familiar snowbird path toward Florida’s warmer weather and sprawling retirement communities, many are sticking to the familiar landscapes and communities of the Midwest by settling in Wisconsin and Michigan…