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 Shake Bar – This brand new (opened Feb. 28th, 2019) 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.Milkshakes piled high with treats from Jojo's Milk bar | Bobby's Bike Hike Food tours

  • 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!
    A variety of churros from Bodega imports | Bobby's Bike Hike Food tours

  • 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.Rainbow colored mini mimosa bomb pastries from Firecakes donuts
  • Hotter Chocolate from Bombobar – Thick, Italian hot chocolate stacked high with donuts, gelato, whoopie pies, and more!
    2 tall glasses of Hot chocolate topped with cookies and treats from Bombobar
  • 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. This one takes the cake for the most extravagant desserts in Chicago!

Marie Antionette cotton candy display | Bobby's Bike Hike food tours


Chicago definitely doesn’t have a shortage of delectable desserts! Sweet tooths are always welcome to join Bobby’s as we romp around the city indulging in decadent and delicious sweet treats. Learn more about our Chicago Sweets & Spirits Dessert Walking Tour which even includes candy-infused cocktails, perfect for bachelorette parties, birthdays, or date night!

Reserve a Tour!