The Ultimate Valentine’s Day Dessert Guide: 5 Sweet Spots in Chicago

Leigh Omilinsky was just nominated for a 2025 Outstanding Pastry Chef James Beard Award and her desserts at Daisies are a playful blend of familiar American comfort food with a sprinkle of Italian influence. Nostalgic Midwest classics like gooey butter cake, warm apple pie a la mode and peanut butter crunch cake appear on the menu with a fine dining flourish, and her housemade gelati and sorbetti (and boozy affogatos) are always a good idea. Daisies is open during the day too, with Omilinsky's pastries filling the case. Look for lemon bars, cookies, kouign amann and limited-edition specials like a ‘Hostess Cupcake’-inspired croissant.

The decadent 12-layer German chocolate cake at this Michelin-starred brewery and restaurant has been on the menu since the restaurant's 2016 opening and is arguably the best chocolate cake in Chicago. It's served a la carte at the Moody Tongue bar and can be ordered online in advance. The cake takes two full days to make and each enormous slice weighs 1.5 pounds, so it's definitely big enough to share. There's even a beer pairing made just for this cake – a bourbon barrel-aged 12-layer cake imperial stout with flavors of coconut and caramel.

Pastry chef Craig Harzewski is a fine dining veteran, and he makes the best traditional French desserts in the city. His warm baked cherry and almond clafoutis with crème Chantilly is a year-round staple and one of the best desserts in Chicago, and seasonal favorites at this elegant French jewel box restaurant might include a warm chocolate tart with Riesling poached pears, or an apple, hazelnut and brioche homage to Normandy served with brown butter ice cream. Pro tip: hand-packed pints of ice cream and sorbet are available to take home, and you can also order a box of delightfully delicate mignardises to go.

This convivial restaurant's global street food theme extends to the internationally-inspired dessert menu, where pastry chef Erin Kobler surprises guests with adventurous flavors like a Thai green curry ice cream sundae with bananas and fish sauce caramel and a Mexican twist on a traditional chocolate tart, with mole spices, tamarind and burnt cinnamon buñuelo. Kobler also makes desserts for Michelin-starred sister restaurant, Sepia, next door, but at Proxi she unleashes her full creative prowess. Unique ice cream flavors like pandan cookies and cream and Vietnamese coffee rocky road are available by the scoop too.

Desserts at Beatnik are bright and colorful, matching the escapism of the restaurant's bohemian décor. Pastry chef Shannah Primiano often uses spices to add an unexpected twist, like Sichuan peppercorns with strawberries in almond mousse, and her baklava cheesecake is a bestselling signature. The phyllo baked crust and creamy filling are finished with pistachios and rose petals for a Middle Eastern touch. For brunch, try the cardamom cinnamon roll for an elegant spin on an American classic with added spice and citrus.