28. Extreme Cupcakes

Location: Sprinkles (50 E Walton St.)
                Flirty Cupcakes (Various Locations)
Website: sprinkles.com
               flirtycupcakes.com

There's far more to extreme food in Chi-town than bottomless deep dish pizza. For starters, try some gourmet, knock-your-socks-off cupcakes. This ain't no kids party fare, friends, these are little bites of heaven. Featured on the Oprah Winfrey Show and the Food Network, head over to the aptly named Sprinkles Cupcakes for some ginger lemon or red velvet—and be prepared to wait in line for them. No better indicator of quality than a line.

If you're looking for something more mobile, keep tabs on Flirty Cupcakes—food truck gone dessert!—where the location changes are as plentiful as the flavors.