Enjoy Festive Flavors with These Holiday Desserts in Chicagoland

The holiday season is such a busy time of the year! If your calendar is packed with holiday parties, performances 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.

Best Christmas and Holiday Desserts in Chicagoland

Santa Brownie Sundae at 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

• Address: 832 W. Randolph St., Chicago

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. 

Winter Wonderland Shake at JoJo’s Shake Bar

• Address: 23 W. Hubbard St., Chicago; 835 Michigan Ave, Chicago; and 5 Jackson Ave., Naperville

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! 

New this year is the Frozen Polar Espresso Martini for grown ups. 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. 

Winter Sleigh Ride Flight at October Cafe

• Address: 6046 N. Avondale Ave., Chicago

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. 

Holiday Donuts at 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, 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, mint hot chocolate, mint mocha, mint chocolate lightning or frosted cinnamon roll tea (available iced, too.) 

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