In terms of skyline-altering projects, construction will begin this year on a 275-unit, 37-story apartment building backed by Chicago developer Carroll Properties, the firm behind a luxury apartment in downtown Evanston and the McGill Mansion conversion on Chicago's South Side. Proposals are floating for a 44-story apartment building hugging Lake Michigan in the shadow of the $76 million tower.

There's so much interest that when Beth Weirick, executive director of business advocacy group Milwaukee Downtown, emceed an event in Brew City for corporate real estate professionals in late October, the crowd of 60 included many wheelers and dealers who drove up from Chicago. “In my generation, Milwaukee has never seen this level of interest,” Weirick says. “We are on the cusp of a fabulous revitalization.”

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Chicago's influence may be most evident in smaller, neighborhood-driven businesses. If you're familiar with Milwaukee, you know that its Third Ward—located just south of downtown—has been ground zero for creative investment for nearly a decade. What used to be low-slung warehouses now are high-end boutiques, restaurants, two art schools and the Milwaukee Public Market, an artisan-foods marketplace in the vein of Seattle's Pike Place Market.

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Spotting a void in the Wisconsin auction market with the closing of Schrager Galleries, West Loop-based antique house Leslie Hindman Auctioneers opened a downtown Milwaukee location in 2011 and followed it with an outpost in the Third Ward two years later. “We love Milwaukee. We've sold a lot of property up there,” Hindman says. In fact, her decision to expand to the Third Ward was validated the day after she opened, when a woman walked in off the street to sell a $600,000 emerald bracelet on consignment. So far, Hindman's four-time-a-year preview events in a Third Ward warehouse draw hundreds.