chicago cupcakes

The making of each cake involves many hours and a great deal of attention to detail. Each one-of-a-kind cake is designed with your theme and personal style in mind, so prices vary per order. Variables include size, complexity of design, flavors and fillings. Please be advised that I am an artist, and not a replicator. If you find a picture of a cake from a third party, I cannot copy this cake exactly. Please have multiple pictures of cakes that you like and I can discuss specific details that you’d like included on the cake.

Serving sizes are based on an industry standard serving chart. The final design of your custom cake will determine any added cost. For example any hand sculpted figurines, edible images, or sugar flowers will be an added expense. Cupcakes must be ordered in dozens. 1 flavor per dozen Smash Cakes: $30 & up (priced based on complexity) smash cakes are 6″ round x 2″ tall cake.

If you would like to continue the ordering process please forward me any pictures you have in mind for a design and I can give you a more detailed quote. Please keep in mind that I take limited amount of orders per week and tend to book up months in advance. Any order placed within 10 days of event is subject to a rush fee of 20%. Please do not hesitate to get a quote.

cupcakes in chicago



Start at $48.00/dozen

  • Chocolate*
  • Red Velvet*
  • Banana
  • Carrot
  • Gingerbread
  • Vanilla*
  • Pumpkin

All of the flavors above come in “mini size for $1.50 each. Flavors available in GLUTEN FREE are marked with an asterisk for $1.00 more.

wedding cakes chicago


Starting at

6″ Round
2 Layers Serves 4-10
6″ Round
3 Layers Serves 8-12
9″ Round
2 Layers Serves 15-20
9″ Round
3 Layers Serves 25-30


12″ Round
2 Layers Serves 35-45


Smash Cake
6″ Cake, Two layers. Custom Decoration


  • Apple Pie
 Apple Spice Cupcake filled with Apple pie filling topped with a cinnamon cream cheese buttercream $5/ea
  • Tiramisu
 Vanilla cake soaked in a espresso kahlua syrup with a mascarpone filling  $5/ea
  • Peanut Butter
Dark Chocolate Cupcake topped with a peanut butter buttercream and a peanut butter mousse center $5/ea
  • Oreo
Dark Chocolate Cupcake  topped with an oreo buttercream and an oreo buttercream center $5/ea
  • Nutella
Dark Chocolate Cupcake  topped with a Nutella buttercream and a Nutella buttercream center $5/ea
  • Cream Cheese
Pumpkin Cupcake topped with a vanilla cream cheese buttercream and a cream cheese center $5/ea
  • Raspberry
Dark Chocolate Cupcake topped with a vanilla bean buttercream and a raspberry center $4/ea
  • Samoa
Dark Chocolate Cupcake with a coconut center, topped with toasted coconut, drizzled caramel and chocolate $4/ea
  • S’more
Dark Chocolate Cupcake topped with a marshmallow buttercream and graham cracker crumble $4/ea
  • Turtle
Chocolate walnut cupcake filled with caramel, topped with chocolate cream cheese buttercream $4/ea

Classic Buttercream Flavor

  • Vanilla Buttercream
  • Salted Caramel Buttercream
  • Chocolate Buttercream
  • Cream Cheese Buttercream
  • Nutella Buttercream


  • Specialty Cupcakes
Specialty cupcakes are available at your request.  Additions may include cupcake wrappers, cupcake toppers or sprinkles.  Fondant toppers require 3 weeks notice.  Pricing varies so inquire within.
  • Delivery
Delivery is available but not included in pricing. Please email with the address and zip code for an exact quote.


Tastings are available by appointment only. There is a $30 charge for a tasting which will be applied to your order if you decide to choose Windy City Dinner Fairy for your wedding.  You may choose 3 flavors to taste at the appointment.  Additional flavors will be an additional charge at $10/each.  There is a $20 cancellation fee if you do not provide notice 24 hours before your appointment.