I don’t want to sound like Debbie Downer, but doesn’t Valentine’s Day qualify as a Hallmark holiday? I always thought the intention was to give greeting card sales a bump and let restaurants build 3-course tasting menus at slightly higher prices for the night. If it truly is a holiday, it’s a high-stress one, because if you’re with someone, there’s pressure of course, to come through with something romantic. If you’re single, there’s pressure to not be totally alone for the night (kind of like New Year’s). Gift givers are forced to tread the delicate line between romantic and cloying, so you procrastinate and then in a last-minute panic you stop on your way home from work and pick up a box of drugstore chocolates, a card, and those AA batteries you’ve been meaning to grab. Please don’t buy chocolates at Walgreen’s. These Chicago chocolatiers and bakeries create sweet treats both classic and unique, and the thought you’ve displayed in procuring them will elevate your gift from merely cliché to truly loving.
2745 W. Armitage; 773-245-1630
Katherine Anne Confections’ chocolatiers craft beautiful and unique chocolates year round, but they’ve outdone themselves this Valentine’s Day with a limited edition Sun and Moon gift box (pictured, above). Meant to be romantic, but not cliché, it contains Sun themed sweets with bright, vibrant flavors that evoke the energy of the sun and more traditional, dessert-like Moon themed sweets. The box itself features gorgeous sun and moon artwork, no wrapping required. The Sun and Moon box costs $65 and can be purchased in the store or online.
For those interested in a more hands-on Valentine’s gift, Katherine Anne is also hosting a truffle-making party on February 11th at 6 pm. Go with your Valentine, or surprise them with a homemade gift. In the the spirit of the holiday, confectioner and founder Katherine Duncan will guide guests in crafting truffles in strawberry, champagne, and other romantic flavors. The cost is $65 per person or $125 for two. Reservations are required and can be made here.
1114 W. Belmont; 773-929-1100
Bittersweet has 20 years of experience in creating quality sweets and pastries. Put that to work for you by picking something from their V-Day menu that has everything from tortes to cookies, with as much chocolate, raspberries, red velvet, and pink icing as your (sweetheart’s) heart could desire. This is the place to go if you want a Valentine’s Day gift that’s not chocolate. Personally, I would go for Judy Contino’s rustic apple tart, it’s the best in the city.
5306 N. Damen Avenue; 773-334-2626
As the name implies, this Andersonville shop specializes in all things chocolate, including a line of vegan chocolate gift boxes. Stop here if your Valentine is vegan or you’re looking for the classier (and tastier) version of the traditional box of chocolates.
4. Sweet Ali’s
13 W. 1st Street, Hinsdale; 630-908-7175
Although stretching the limits of “Chicago bakeries,” Sweet Ali’s made it on the list by virtue of their extensive selection of gluten-free sweets and the fact that their products can be delivered throughout Chicago via Artizone. They’ve got nostalgia inducing conversation heart cookies, cupcakes in a variety of flavors, and they take orders for custom sweets.
2409 N. Western Avenue; 773-998-2462
Named one of the best chocolates in the U.S. by Food & Wine Magazine, Veruca Chocolates has an array of luxury bonbons, caramels, and chocolates in traditional flavors as well as unique ones like lavender and saffron. They also have a special collection of visually stunning Valentine’s Day Chocolates.