Terry's Toffee's Peppermint Pistachio Crunch Ice Cream ($6.99 a pint)
Skip the one-note peppermint pistachio toffee in favor of its premium ice cream counterpart. It's simply a mild peppermint ice cream with substantial chunks of peppermint-flavored toffee—some half melted and others retaining their hearty crunch.
Andy's Frozen Custard's Candy Cane Concrete ($4.38)
Custard can be a heavy, albeit heavenly, treat, but the candy cane pieces make this concrete lighter—almost refreshing. The vanilla and peppermint flavors shine through equally in a creamy and crunchy concoction not comparable to many other desserts.
Bittersweet Pastry Shop & Cafe's Chocolate Peppermint Cake Pop ($2.00)
You could easily write off a cake pop as a fad unworthy of serious consideration, but the pastry chefs at Bittersweet won us over. The pop has a dense, fudgy core with a crunch from both the chocolate shell coating and the candy cane pieces. This is a good option if you want to celebrate the season without ruining your appetite for one of Bittersweet's myriad other quality treats.
Fannie May's Peppermint Bark ($24.99 per pound)
There's nothing revolutionary about the peppermint bark from this Chicago original, but it is done well. Equal parts high-quality white and dark chocolates combine to make a thick bark that has a surprisingly easy bite with just a smattering of crushed peppermint sprinkled on top.
Bobtail Ice Cream Company's Peppermint Stick Ice Cream ($3.19)
If you really want to go all out for that it's-Christmas-and-I-just-ate-half-a-dozen-candy-canes-off-the-tree kind of feeling, stop by one of Bobtail's three Chicagoland locations for a scoop of their seasonal Peppermint Stick ice cream. We're fairly certain a one-scoop serving includes an entire candy cane. Luckily the peppermint is tempered by their ultra creamy ice cream base.
We also tried Bobtails' Peppermint Ice Cream Latte ($3.49). The lack of chocolate in this latte is a welcome variation, making a drink that can easily seep into cloying territory (read: Starbuck's) seem lighter. For an even more refreshing treat, pour a little of the latte on top of the candy cane ice cream for a seasonal affogato.
The Walnut Room's Frango Mint Chocolate Ice Cream Pie ($4.95)
The Frango Mint Chocolate Ice Cream Pie at the most famous department store restaurant in town is a simple indulgence. The ice cream is a smoother version of mint chocolate chip with a nice textural contrast from the hearty graham cracker crust. The whipped topping is a decorative afterthought and almost makes you wish for a generous dollop of real whipped cream, but the extra creaminess really isn't necessary. Consider this a cool alternative to the ubiquitous after-dinner mint.
Bleeding Heart Bakery's Vegan Chocolate Cupcake with Peppermint Frosting ($2.50)
The cake at Bleeding Heart is remarkably moist with a delicate but not overly-fragile crumb. The peppermint frosting tastes great, even if it doesn't provide as smooth of a bite as other non-vegan cupcakes. Luckily, the combo works well, and it gets bonus points for being vegan. Better hurry though, it's the December flavor of the month.
Peppermint Pistachio Crunch Ice Cream
From Terry's Toffee in West Town. —Lindsey Becker