Bar Siena's walk-up dessert window, BomboBar, offers a riff on doughnuts - the "bomboloni" - an Italian hole-less doughnut Top Chef alum Fabio Viviani serves at his restaurants, Siena Tavern and Bar Siena. It's the specialty of the house at BomboBar and works wonderfully in the West Loop for dessert or post-party hunger pangs. Order one, four, six or a dozen and any of six rotating custard flavors that you inject into the doughnut. There's Vanilla Bean Custard bomboloni, S'mores bomboloni, Salted Caramel and Nutella. Bomboloni is made-to-order and fried on-site then rolled in sugar and accompanied with its very own squeeze bottle of custard. Pair it with hot chocolate concoctions (spiked, too) or creamy gelatos with toppings. BomboBar has a 24-person seating area to stay warm when the weather BomboBar opens another location in Old Town in 2019.
Recommended for Dessert because: A walk-up window offering hot Italian donuts in the West Loop, BomboBar hits the spot for dessert or round-the-clock sugar needs.
Jacky's expert tip: Come by in winter, too, since there's a 300-square-foot, heated vestibule to keep you toasty while you wait for bomboloni.
The main draws at this hip, cozy spot by James Beard Award-winning pastry chef Mindy Segal, are the impressive gourmet desserts, ice cream and the titular hot chocolate. If you don't know where to start, feel free to quiz waitstaff who are very knowledgeable and accommodating. Thick, steamy Mexican hot chocolate, a mix of dark and milk chocolate and a dash of cinnamon, is just the thing to get you through a winter day in Chicago. That's not to say Mindy's is just for Polar Vortex weather. There are rich milkshakes like a stout and caramel or triple vanilla plus pineapple sorbet and mint chip ice cream to cool off and still get your sugar rush. Pair a dessert with a cocktail (or add some spirit to your hot chocolate). The menu may offer banana brioche bread pudding; butterscotch pot de creme; or a cake of the moment.
Recommended for Dessert because: Although Mindy's offers breakfast, brunch, lunch and dinner, the hot chocolate, pastries and sweets keep the place buzzing.
Jacky's expert tip: There's a $15 per person minimum for "dessert only" reservations.
Superlative desserts at a tavern? Irish owned but utterly American, The Dearborn can be found at the intersection the Theater District, satisfying food and lively ambiance. Pastry Chef Julianna Westgor has a playful style riffing on ice cream truck treats in the summer and warming things up in the winter with adults only hot chocolate and fried banana bread with hazelnut chocolate ganache, malted milk jam and hazelnut crunch ice cream. Her peanut butter chocolate dream is just that and don't leave without someone ordering the gooey butter cake with burnt honey ice cream and orange caramel drizzle. Her churros change seasonally (Caramel Apple or Cinnamon Spice Churros, which combine pumpkin white chocolate mousse with Rumchata ice cream and a warm toffee pour. Other desserts are inspired by seasonal fruits - key-lime blueberry-pie ice cream anyone? Couple any choice with local and rich Big Shoulders coffee.
Recommended for Dessert because: In the Theater District, the Dearborn's inventive dessert program is perfect for those in need of pre or post-show sugar.
Jacky's expert tip: Although it's is located in Block 37, a shopping center in the heart of the Loop, the entrance is on the corner of Dearborn and Randolph.
Everything is made right in Katherine Anne's retail space, so you can see them rolling truffles, pouring caramel and whipping marshmallow. The cafe has 16 seats for enjoying 15 flavors of drinking chocolate or sweets. Chocolatiers make a new truffle and caramel each week just for the shop, and they like to experiment. Like what? How about an Everything Bagel caramel? You can count on favorites such as the Caramel Latte truffle (with Ipsento coffee, roasted just four blocks away), the Goat Cheese Walnut truffle with chunks of fresh chevre, and the Citrus truffle with lemon, orange, lime and lemongrass. Yes, it's indulgent but know that the shop uses fine, local ingredients, down to the cream from a herd of Jerseys in central Illinois and local wildflower honey that replaces corn syrup.
Recommended for Dessert because: It's a small but busy cafe for drinking chocolate with truffles, caramels and marshmallows handmade on-site using fresh. local ingredients.
Jacky's expert tip: Put together a bachelorette, birthday or company truffle-making party at Katherine Anne Confections.
Sometimes, whether to enhance celebration or assuage gloom, you just need a ginormous honking dessert. The 23 Layer Chocolate Cake at Michael Jordan's Steakhouse outdoes the colossal creations of other steakhouses with 23 layers of chocolate ganache topped with whipped cream. It's not just big - it's delicious and a wonderful way to share a chocolate confection. There are other extremely satisfying desserts on the menu including a luscious peanut butter pie (with a chocolate crust); mixed berry mascarpone cheesecake; caramel apple bread pudding; pecan tart sided with praline ice cream; and grapefruit and blood orange panna cotta with rosemary shortbread. Order dessert wine or a sturdy cup of locally roasted Metric Coffee and button up a fabulous dessert experience.
Recommended for Dessert because: Michael Jordan officially took Al Capone out as the historic name most associated with Chicago - that and the food is spectacular.
Jacky's expert tip: Need more chocolate? Eno Chicago Wine Bar is adjacent to MJ's and features fine vintages, brilliant cheese and chocolate tastings and an outdoor patio for people watching.
The River North restaurant offers a menu of sophisticated Parisian dishes that land upon exquisite china amid French linens. That includes painterly desserts by Pastry Chef, Craig Harzewski, who grabbed a 2019 nomination for a Jean Banchet award. Harzewski, who worked for celebrated Pastry Chef, Francois Payard at Payard's, and at Le Cirque in NYC, displays his talent for fine French pastries and chocolates nightly. Expect seasonally tweaked selections such as autumn spiced créme bruleé with French salted butter cookies, seasonal fruits, black tea and cider sorbet or warm baked almond scented clafoutis (arranged in a buttered dish and covered with a thick flan-like batter) with créme Chantilly. Someone should order the Delice of E. Guittard 150 Year Anniversary Chocolate, with dense, soft, classic milk chocolate cremeux, gold leaf and sea salt. Coffee, Cognac, a nice tawny Port or other sweet wine make a grand conclusion.
Recommended for Dessert because: Any list of "best desserts" must include at least one French restaurant or we'd be beaten with a baguette - and Brindille is a top choice.
Jacky's expert tip: It's French so cheese is also dessert. Choose among 12 varieties of French artisan cheese, served with fruit compote and seeded raisin ficelle.
Just a few minutes from Millennium Park (and another location on Wacker and LaSalle), Goddess and The Baker is open for breakfast, lunch, dinner, and dessert all day. In fact, dessert is their jam: among the temptresses in the display case are the popular layered rainbow cake, cupcakes, muffins, macaron cookies, jars of sweetness, pastries, bars and brownies. Pair any with a scoop of Zarlengo's rich, local, Italian gelato. The coffee menu is impressive and ranges from Goddess gringo horchata and spicy Mayan Mocha to specialty sips like Gold Glitter latte. Goddess and the Baker offers milk alternatives for your coffee drinks including various nut milk, soy and oat at no extra charge. Combine caffeine and dessert with buzzed liquid chocolate with two shots of espresso and whip. The rotating selection of beans from third wave roasters means even a regular cup of joe is anything but.
Recommended for Dessert because: Specializing in dessert all day, Goddess and the Baker focuses on house-made pastries and sweets, plus a one-of-a-kind coffee program all just steps from Millennium Park.
Jacky's expert tip: The pretty but small space can get crowded near breakfast and lunchtime, so go in between or around dinner if busyness is bothersome.
Located in Andersonville, Manor, Evanston and Ravenswood, First Slice Pie Cafe specializes in hearty soups and sandwiches plus homey baked goods made from scratch. Another treat is knowing that a portion of its proceeds benefit the needy and homeless because the cafes are self-funded charities. There are creampies from Pumpkin Cheesecake with a gingersnap crust to Key Lime and Coffee Toffee. Get your fruit serving in a wily way by tucking into Michigan Sour Cherry or Balsamic Raspberry Pear Pie. The Andersonville location has open mic nights so you can pair pie with tunes. Look into Its weekly shareholder's program and receive home-cooked, restaurant-quality meals weekly. Those funds are used to make the same quality meals for people in need. Let's eat pie to that idea!
Recommended for Dessert because: Eating handmade pie feels even better here. First Slice gives back a portion of its proceeds to feed the homeless and those in need.
Jacky's expert tip: Consider having lunch before pie. Where else can you taste salads straight out of the 1970s like Mango Jicama, Mimi's Tuna or Curry Chicken?
Bakery and Chicago history fans lamented when Swedish Bakery closed after 88 years. Pastry chef and Chicago native, Bobby Schaffer, did the city a favor when he and his sister, Bree, opened Lost Larson. Expect seasonally inspired pastries bursting with ripe fruits, hand-rolled cinnamon rolls, cardamom buns and aromas so heavenly you might think you should pay for them, too. Schaffer led the pastry program at three-star Michelin restaurant, Grace, and studied under a Spanish master chocolatier. His dedication is indicative with pastries such as Duchess Cake (vanilla sponge, raspberry, white chocolate marzipan mousse); Pistachio Cherry Tart; and lovely everyday items including chocolate spelt cookies, chocolate hazelnut croissants, lingonberry almond cake and tebirkes - poppy seed pastry. Try any of the open-faced sandwiches (pickled herring or green onion avocado among others) available during lunch hours.
Recommended for Dessert because: A brother and sister with Scandinavian roots offer artisan pastries and bread baked fresh daily in historically Swedish Andersonville.
Jacky's expert tip: Lost Larson makes and bakes bread every day using freshly milled, local flour, so take home a loaf of the Swedish limpa redolent of fennel, anise and orange peel.
Veruca began as a wholesale business and today anyone can sample the variety of handmade, artisan chocolates and caramels made for those with a discerning taste for fine chocolate and an eye for beauty. Each piece is handmade and hand decorated to entertain more than one sense. Everything is made from scratch in the Lincoln Park kitchen from year-round to seasonal products for Valentine's Day (natch), Christmas, Hanukkah and Halloween. Signature bonbons feature unique flavors inside and bright colors outside (try milk and dark chocolate with brown butter or Champagne truffles). Don't leave without sampling the signature sea salt caramel enrobed in 64% dark chocolate which was named one of 25 best chocolates in the US by Food and Wine. Add some drinking chocolate and you'll be all set for another day. Consider taking a public or private class to get your hands directly into the chocolate making process.
Recommended for Dessert because: Veruca Chocolates, handmade and decorated in Lincoln Park, are some of the finest artisan chocolates in the city if not the country.
Jacky's expert tip: The Chicago flight of chocolates dons designs of city landmarks. The Bean design is coffee flavored inspired by Metropolis Coffee Company and the Ferris Wheel is inspired Ann Sather's iconic cinnamon buns.