26 College Towns That Feel Like Mini Versions of Major Cities

Lisette Marie

November 7, 2025

7. Madison, Wisconsin – The Midwest’s Mini Chicago

The Lake Mendota shoreline is pictured in an aerial view of the University of Wisconsin-Madison campus looking toward the downtown Madison skyline during an autumn sunset on Oct. 5, 2011. Major campus facilities pictured from center to right include Memor. Photo Credit: Wikimedia Commons @college.library

Madison offers all the culture, food, and entertainment of a big city, packed into a more intimate, lakefront setting. The University of Wisconsin fuels a progressive, entrepreneurial energy, and the town’s restaurants, music venues, and festivals rival those of much larger urban centers. With strong Midwestern roots and a lively waterfront, Madison is like a mini Chicago, but friendlier and more walkable.

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26 College Towns That Feel Like Mini Versions of Major Cities

7. Madison, Wisconsin – The Midwest’s Mini Chicago

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