It’s no secret that Chicagoans know how to eat. It’s also no secret that our recipes tend to be a bit over the top. We take pride in that! While visiting Chicago, you have to try our deep dish pizza and you have to try our fully-loaded Chicago dog, but what should you do for dessert? Why not keep on with the outrageous and extravagant theme, and try one of the following creations from a few Chicago sweet tooth experts. These are some of the Bobby’s staff’s favorites, perfect for indulging after a long and satisfying bike ride.

  • Milkshakes from JoJo’s Milk Bar – This brand new (opened Feb. 28th) neo-diner is serving up tricked out shakes, loaded and topped with cake, candy, cookies, pie, and more. Add a shot of whiskey for an extra kick of fun.
  • Dessert Tacos from Parlor Pizza Bar’s Dessert Dealer – These sweet waffle taco shells are loaded with gelato and indulgent toppings, ranging from gummy worms to Thin Mints, pretzels, hazelnuts, and rainbow Airheads.
  • Churros from Bodega Imports – This local hotspot takes the Mexican treat to new heights. Flavors include red velvet, fruity pebbles, oreo, nutella, and a rotating seasonal surprise—you’ll just have to try one of each!

  • Mini Mimosa Bombs from Firecakes Donuts – These little wonders are only available seasonally in June, but as soon as they are, the masses will flock. They are exactly like they sound: little balls of boozy sunshine.
  • Hotter Chocolate from Bombobar – Thick, Italian hot chocolate stacked high with donuts, gelato, whoopie pies, and more!
  • Spumoni Pie from Bang Bang Pie & Biscuits – Pistachio pastry cream, dark chocolate ganache, cherry whipped cream, candied pistachios…your favorite ice cream shapeshifted to fit inside a graham cracker crust.

  • Blueberry French Toast Gelato from Black Dog – This gelato is rich, creamy, and nuanced in flavor; a one-of-a-kind Chicago treat.

Don’t forget the grand finale…

  • The Marie Antoinette Head (Let Them Eat Cake!) from Barton G – This legend is a three-foot tower of cotton candy on top of a Marie mannequin head, surrounded by cupcakes and candy.