1. Utopian Tailgate
Old Town
Just above Second City, Utopian Tailgate offers just what you’d imagine: the ultimate tailgating experience (without having to stop for sports). The 10,000-square-foot indoor/outdoor space has everything you need for a fun (albeit kitschy) time, from canned wines to colorful cocktails with little paper umbrellas, and large-format drinks with names like Squad Goals and Go Fish, not to mention plenty of games to play with your crew. Eats include crispy fried chicken sliders on sweet Hawaiian buns and a foot-long Chicago-style hot dog. If you still have room, treat yourself to a Waffle Boyz waffle, topped with ice cream, maple syrup, caramelized bananas, and crunchy pecans.