Add some sugar to the sweetest day of the year with one of these extra special Valentine’s Day treats. From shareable date night desserts to special treats to share with your littles and loved ones, these treats are the yummiest way to say “I love you!”
Best Valentine’s Day desserts in Chicagoland
Old Skool Chocolate Covered Strawberry Roll at Cinnaholic
- Locations in Burr Ridge, Chicago, Evanston, Naperville and Schaumburg
Would you believe me if I told you that cinnamon rolls taste even better on Valentine’s Day? At least, the Old Skool Chocolate Covered Strawberry Roll at Cinnaholic does! Enjoy a vegan cinnamon roll topped with a chocolate-covered strawberry, more chocolate drizzle and a dusting of powdered sugar.
The bakery is also offering chocolate-covered strawberries with sprinkles, chocolate chips and more sweet toppings for a limited time.
Valentine’s Igloo Treats at Creamery
- Participating locations in Homer Glen, Lombard and Manhattan
The festive igloo experience at Creamery is a great way to turn a decadent dessert into a memorable experience for the entire family. Select an adorable Valentine’s Day ice cream treat from the exclusive igloo menu, then cozy up with your loved ones in a private igloo that is decked out in red and pink decor.
Special Valentine’s Day offerings include a Cookie Dough Crush sundae topped with a chocolate chip cookie dough ice cream sandwich, a Strawberry Cheesecake Milkshake, the Cloud 9 mason jar sundae and the Cupid’s Flight, composed of five premium ice cream sandwiches.
Love Shake at JoJo’s Shake Bar
- Address: 23 W. Hubbard St., Chicago and 5 Jackson Ave., Naperville
Love is in the air and Valentine’s-themed decor is all over at JoJo’s Shake Bar. Their seasonal red velvet and raspberry Love Shake is topped with a sugar cookie heart, chocolate-covered pretzels and strawberries and an entire slice of cheesecake!
If you prefer to sip on something warm, try Cupid’s Cocoa. The red velvet hot cocoa is loaded with yummy treats, including chocolate-covered s’mores, pretzels and marshmallows.
Pink Ice Cream at Lola’s Handcrafted Churros
- Address: 4714 Main St., Lisle
At Lola’s Handcrafted Churros, you can order a cup of pink soft serve all year-round! Pair the perfectly pink ice cream with a strawberry-covered churro for a red and pink Valentine’s treat.
Love is in the Air Flight at October Cafe
- Address: 6046 N. Avondale Ave., Chicago
This sweet combination of seasonal drinks is love at first sip! The Valentine’s beverage sampler includes a chocolate and sun butter latte; a strawberry hot cocoa; an Earl Grey vanilla tea latte; and a red velvet latte. Each flight will be served on a tray with cute holiday decor and chocolate hearts.
The 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 needs.
Valentine’s Ice Cream at The Original Plush Horse
- Address: 12301 S. 86th Ave., Palos Park
A trip to an old-school ice cream parlor is a great way to show some love to anyone with a sweet tooth. For your next ice cream outing with your sweethearts, head to The Original Plush Horse to try one of their seasonal Valentine’s flavors: Strawberry Chip and Chocolate Cherry Kiss.
Valentine’s butter cookies and heart-shaped sprinkles are available to add the perfect touch to your Valentine’s treat.
Chocolate Covered Strawberry Shake and Heart Shaped Chocolate Cake at Portillo’s
- Locations throughout Chicagoland
If you love the classic Portillo’s Cake Shake, then you’ll be head-over-heels for the Valentine’s edition: a Chocolate Covered Strawberry Shake! The shake combines fresh strawberries with swirls of the famous Portillo’s chocolate cake frosting.
For a dessert the entire family can share, pre-order a heart-shaped Portillo’s chocolate cake. For each cake ordered, Portillo’s will donate $5 to the nonprofit No Kid Hungry.
Valentine’s Day Donuts at Stan’s Donuts
- Locations throughout Chicagoland
Tell your valentine you donut know what you’d do without them (we had to include at least one cheesy Valentine’s pun!) with one of Stan’s seasonal donuts. This year’s Valentine’s treats include heart-shaped donuts, heart sprinkle donuts and red velvet mini donuts.
Red Velvet OMG at XO Marshmallow
- Address: 2730 N Clark St., Chicago
Omg! The Red Velvet OMG (short for ooey marshmallow goodness) is here for Valentine’s Day! What child wouldn’t love digging into a pint of cream cheese fluff with chocolate and red velvet cake pieces? Use the treat for dips, frosting or a hot cocoa topper, or simply enjoy it with a spoon!
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This article was recently updated on Feb. 10, 2025 by Chicago Parent’s writer, Sarah Knieff. The update included her research to feature the latest information. Questions? Please reach out to editor@chicagoparent.com.
