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Utopian Tailgate is a bar on top of the Second City building in Old Town, and unsurprisingly, their menu is tailgate-themed, so expect food like nachos, pizza, and skewers. It reminds us a lot of a rooftop version of Paradise Park—meaning astroturf, lots of colorful patio furniture, and things like swing sets and giant Jenga. The only difference is that here, a fun DJ set and game of bags will be accompanied by a great city view.