Deck the Halls with These Amazing Holiday Treats in Chicagoland

Make merry with these festive desserts!

The holiday season is such a busy time of the year! If your calendar is packed with holiday parties, performances, festive activities and shopping, you deserve a break — and something sweet! 

Treat the family to an indulgent holiday dessert at these local spots right here in Chicagoland. From Christmas doughnuts and festive coffee flights to hot chocolates and milkshakes topped with delicious seasonal treats, there’s no better time to indulge your sweet tooth than during the holiday season. 

Santa Brownie Sundae at Andy’s Frozen Custard

Photo courtesy of Andy’s Frozen Custard

  • Address: Locations throughout Chicagoland

Loaded with brownies, hot fudge and candy cane pieces, the Santa Brownie Sundae is a festive twist on Andy’s classic frozen custard sundaes. You also can enjoy the treat as one of their signature Jackhammers, which is vanilla frozen custard blended with candy cane and brownies, then filled down the center with hot fudge. 

Not a big fan of chocolate? Andy’s is serving up creamy eggnog shakes this season! 

Festive Hotter Chocolate at BomboBar

Photo credit: BomboBar

The walk-up window at BomboBar is known for its over-the-top Hotter Chocolate. This holiday season, you can go traditional with rich hot cocoa topped with whipped cream and chocolate shavings, or go all out with the S’more Hotter Chocolate — cocoa topped with marshmallow fluff, chocolate drizzle and a graham cracker biscotti. Grown-ups can spike their warm bevys with Jameson or Baileys

Wreath Cakes at Cinnaholic

Photo credit: Cinnaholic

This vegan bakery is serving two festive flavors of cinnamon rolls this season: Santa’s Milk and Cookies and Gingerbread House. Take the treat up a notch by ordering an entire Wreath Cake of your favorite holiday flavor, or create your own cinnamon roll cake by choosing your favorite frosting and up to three toppings. 

Winter Wonderland Shake at JoJo’s Shake Bar

Photo credit: JoJo’s Shake Bar

Any Chicagoan with a sweet tooth knows that JoJo’s is the go-to spot for an over-the-top dessert any time of year. The next time you’re in the mood for a milkshake, get into the holiday spirit with JoJo’s Winter Wonderland Biggie shake. The supersized milkshake is topped with red and green sprinkles, a sugar cookie and a snowman made out of doughnut holes! 

JoJo’s is also serving up Peppermint Party Hot Chocolate in addition to its four other hot chocolate offerings. Grown-ups can spike their drinks with Baileys or Jameson. 

Christmas Churros at Lola’s Handcrafted Churros 

Lola’s is known for its hot and crunchy, cool and creamy churro loops served over cups of soft serve ice cream. If it’s too chilly for ice cream this winter, enjoy a Christmas churro loop. The oversized churros are decked out in white and green frosting and red, green and white Christmas sprinkles. 

Winter Sleigh Ride Flight at October Cafe

Photo credit: October Cafe

October Cafe is a year-round fall-themed coffee spot where you can always find fall coffee flights, pumpkin-flavored everything and cute fall decor. This holiday season, the Norwood Park cafe is offering a Winter Sleigh Ride Flight so you can try small pours of all four of its winter coffee specials! 

The four flavors are a pumpkin spice and salted caramel latte; peppermint and white chocolate cocoa; matcha tea latte with simple syrup; and chocolate chip mocha latte. Each flight is offered caffeinated or decaf, hot or iced, and with your choice of milk, so it’s completely customizable to your family’s tastes and dietary restrictions. 

Grinch Ice Cream at The Original Plush Horse

We’ve seen a lot of limited edition Grinch-themed treats this season, but the Grinch Ice Cream at Plush Horse is here to stay all season long! The green Amaretto ice cream is filled with cookie dough, brownie bits and holiday M&Ms. Add crushed peppermint for that extra holiday kick! 

Candy Cane Hot Coco at Pretty Cool 

Photo credit: Pretty Cool

Pretty Cool specializes in unique and unexpected ice cream flavors, but when the temperature starts to drop, it takes its hot cocoa game seriously! 

Enjoy a rich and creamy cup of hot coco topped with marshmallows, or enjoy a dairy-free coconut-based coco. Pretty Cool also offers a take-home kit so you can make your own hot coco. 

Holiday Donuts at Stan’s Donuts

Photo credit: Stan’s Donuts

  • Address: Locations throughout Chicagoland 

Chicago has loved Stan’s Donuts since the first Chicagoland location opened nearly a decade ago. Celebrate the season with this year’s holiday donuts — Gingerbread Stan, Sugar Cookie, Peppermint Bark Old Fashioned and even a gluten-free gingerbread donut.

You can also pair your favorite specialty donut with one of Stan’s winter drinks: winter cherry vanilla refresher, matcha cinnamon latte, peppermint bark hot chocolate, peppermint latte or a mint tea.

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