Bobtail Ice Cream was born out of a business plan competition at The University of Chicago Booth School of Business, and inspired by the grandfather of one of the founders (Grandpa Wilcoxon) who sold ice cream door-to-door from a truck in his Ohio neighborhood in the 1950s. The ice cream here is hard-packed and homemade, a mix of expected flavors and specialty creations, like Merlot ice cream with dark chocolate chips. And for those cold, windy Chicago days, there are some more weather-appropriate options, like hot fudge on a warm brownie, ice cream lattes, hot chocolate, and white mocha.

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