Winter Drinks and Bakeries

The Home Remedy

Got a case of the cold weather blues? Pleasant House Pub in Pilsen has a fix for that: a cocktail called the Home Remedy. The bartenders mix ginger fizz, chili liqueur, and a hint of maple syrup with a hefty dose of scotch to create a beverage that will kill any chill. “It’s a warming and zippy addition to our winter cocktail menu,” said Evan Walters, the bar manager. Pair it with one of their namesake savory royal pies—available with both meat and vegetarian fillings—for the ultimate cozy indulgence. (Carly Graf)

Pleasant House Pub, 2119 S. Halsted St. Tuesday–Thursday and Sunday, 10am–10pm; Friday–Saturday, 10am–midnight; Monday closed. (773) 523-7437. pleasanthousepub.com

Cafe de Olla

Though available year-round (hot or iced), Build Coffee’s cozy, inviting Cafe de Olla—made with spiced brown sugar, and, ideally, oat milk—feels like it could be enough, by itself, to power you all the way through winter. (Sam Stecklow)

Build Coffee, 6100 S. Blackstone Ave. Monday–Friday, 8am–5:30pm; Saturday, 9am–5:30pm; Sunday, 9am–3pm. Closed December 23–January 1. buildcoffee.org

Dirty Abuelita

When eyeing the drinks menu at the counter, of La Catrina—a Pilsen staple since 2013—one of the drinks that stands out the most is the “Dirty Abuelita” ($3.75–$4.25) The hot chocolate is made from an Abuelita-brand chocolate tablet that is melted down with milk; then add a shot of espresso, and you’ll get a cozy drink that’s the best part of childhood and adulthood put together. Available year-round, it’s the get-up-and-go-beverage you need to tackle holiday shopping. (Sarah Thomas)

La Catrina Cafe, 1011 W. 18th St. Monday–Thursday, 7am–9pm; Friday–Sunday, 8am–6pm. (312) 532-6817. facebook.com/lacatrinacafeon18

The Chai Pumpkin

This cozy restaurant has a menu of eleven-dollar cocktails, the most Christmassy of which is the Chai Pumpkin ($11), served with a dash of nutmeg on a delicate layer of sweet foam. With its rich brown body and frothy white coat, the drink looks like a slice of pumpkin pie topped with whipped cream and tastes like eggnog’s boozy older sibling. Its two ounces of rum isn’t overpowering and blends nicely with the other ingredients, including pumpkin seed milk and chai syrup. Best sipped gazing out of the restaurant’s two walls of windows on a snowy winter afternoon. (Tammy Xu)

The Promontory, 5311 S. Lake Park Ave W. Monday–Thursday, 5pm–11pm; Friday, 11am–1am; Saturday, 9am–1am; Sunday, 9am–11pm. (312) 801-2100. promontorychicago.com

Toasted Marshmallow Latte

Holiday drinks are usually made up of ingredients that remind you of winter: peppermint, chocolate, cloves, pumpkin. But from the menu of Brew Brew, one of Pilsen’s newer coffee shops, comes a drink that focuses in on what is usually one of the best toppings on hot drinks: marshmallows. The Toasted Marshmallow latte lives up to its name. The flavor and aroma of a marshmallow that has just been kissed by the fire is present from the first sip to the last. Smoother and less sticky than drinking actual melted marshmallows, this beverage is a tasty choice for a holiday drink. (Sarah Thomas)

Brew Brew Coffee + Tea, 1641 W. 18th St. Monday–Friday, 7am–5pm; Saturday–Sunday, 8am–5pm. (312) 796-3151. brewbrewcoffeeandtea.com

The Black Phillip

Bring your appetite when you head to Bridgeport’s Jackalope Coffee & Tea House, a neighborhood joint known for its whimsical interior, decadent winter drink menu, and sandwiches named after mythical creatures. But if you only try one thing, make it the Black Phillip. The indulgent concoction, whose namesake is the demonic goat that stars in the 2015 film The Witch, is made from espresso, steamed milk and goat milk caramel, all topped with Hawaiian black lava sea salt. (The Black Phillip can easily be made vegan, too.) If you’re a real Witch fan, come early enough in the day and you might snag the highly-coveted “wouldst thou like to live deliciously” Black Phillip mug behind the counter for the full experience. (Carly Graf)

Jackalope Coffee & Tea House, 755 W. 32nd St. Monday–Friday, 6:30am–8pm; Saturday, 7am–8pm; Sunday, 8am–7pm. (312) 888-3468. facebook.com/JackalopeCoffeeAndTeaHouse

The Scrooge

I’ve never had eggnog before, but Carlos, the cheerful owner of Kristoffer’s Cafe & Bakery in Pilsen, encouraged me to switch up my iced coffee (no milk or sugar) routine with The Scrooge, a popular holiday drink that Kristoffer’s has served for the past four years. Thanks to Carlos, my memories of snowy days as a kid returned as I continued my commute to work. The Scrooge blends steamed eggnog with “direct trade black cat espresso from Intelligentsia,” but its description only provides a glimpse of its full flavor. As I sipped away, I tasted the soft whipped cream swirl with the carefully crafted ingredients—the flavors tasted a little different each time. With the drink providing much-needed warmth, I walked down Halsted to catch the 8 bus and kick off my day. Next time, I’ll make sure to sit down to enjoy The Scrooge with Kristoff’s famous flan alongside my eight-year-old niece Adeline, who loves their Mayan Hot Chocolate. (Jocelyn Vega)

Kristoffer’s Cafe & Bakery, 1733 S. Halsted St. Tuesday–Friday, 7:30am–5pm; Saturday–Sunday, 8am–4pm. (312) 829-4150. kristofferscakes.com

Jolly Saint Mint

Heritage Cafe, 1849 E. 79th St. Monday–Friday, 7am–3pm; Saturday–Sunday, 9am–3pm. (773) 530-0045. heritage1849.com

On a cloudy Saturday afternoon, Heritage Cafe is a warm refuge from the busy, slushy 79th Street corridor outside. Straddling the line between South Shore and South Chicago, the husband-and-wife coffee shop launched earlier this year as a full-time passion project. The inviting, comfortable space of the shop serves as a gathering spot for community activists, entrepreneurs, and artists. It’s the kind of place where you’ll hear snippets of conversations about the merits of Theaster Gates’s Rebuild Foundation projects over the track-to-track transitions of a techno DJ, all while neighbors stop by to contribute to a charity clothing drive. Despite being a newcomer to the South Side café scene, it’s already an effective example of how a coffee shop can function as a miniature community center.

This December, I’ve found love in one of Heritage Cafe’s three holiday-themed drink specials: the Jolly Saint Mint, which is made with Heritage’s “Exquisite” house blend of coffee, bourbon caramel, and peppermint. And since Heritage is an all-vegan affair, I chose between five non-dairy milk options. My preference was for hemp milk, which adds a nutty flavor to the smoothness of the bourbon, and helps to tame the mint. (Soren Spicknall)

Gingersnap Latte

There are so many indicators that the holidays are coming: Christmas lights, holiday commercials, and the return of spice-filled holiday drinks. The Gingersnap Latte at Pilsen’s newest coffee shop, Intersect Coffee, is yet another sign. Like most lattes, this one has a silky quality, with a delicate layer of foam atop. But the real star of the drink is the homemade gingerbread syrup. Johnny Dean, the lead barista and creator of the syrup, says he wanted to keep things simple. “One of my favorite cookies is the gingersnap, so that’s why I came up with it.” he said. When you want a break from the chocolate-heavy holiday drinks that dominate most café menus, try spicing it up with a Gingersnap Latte. (Sarah Thomas)

Intersect Coffee, 1727 W. 18th St. Tuesday–Saturday, 7am–7pm; Sunday, 8am–5pm. (312) 846-6805. instagram.com/intersectcoffee

Akhirah’s Praline Candy & Coffee House

A few blocks north of Chinatown, at the meeting point of Archer Avenue and State Street, lies a portal to the Paris of the South. Akhirah’s Praline Candy, Beignets & Coffee is Chicago’s access-point for New Orleans-style rum-spiked treats and coffee. Winter has the tendency to orient us toward the comforts of warm, sugary pastries and the need for a setting that will momentarily allow us to forget words like chilly, frigid, or long. Invite a friend, coworker, new or current partner (spare them the details as to what or where because surprises are far more exciting) for a date at this South Loop gem, your soon-to-be-favorite winter-time date spot. Nowhere else in the city can you order three made-on-the-spot beignets for $5.19. They come out piping hot and doused in powdered sugar, looking as powerful as the blizzard that cancelled those 700-something flights over Thanksgiving. Each bite will land your teeth onto a sugar-dust crust, then you’ll break past the crispy mantle and discover the doughy core which will make your brain ooze with a collection of your happiest memories.  

So, what to bring to that holiday party you have coming up? In the face of so many overdone or expected desserts and dishes, you can only impress with one of Akhirah’s praline candies. Order a dozen for $28.68 and try flavors that range from plain or rum with no nuts, to plain or rum with pecans or cashews, to cranberry and sunflower seeds. While you’re sipping on mulled wine as a guest–or host–at the next holiday party you can tell guests all about the beignets you ate while waiting for your candy to be wrapped. Who knows? Maybe it will start a new December tradition. (Leo Williams)

Akhirah’s Praline Candy & Coffee House. 1845 S. State St. Monday–Friday, 6am–7pm; Saturday–Sunday, 8am–6pm. (312) 985-1101. facebook.com/Akhirahs

Fabiana’s

Fabiana Carter describes her bakery as “a place where everything is made from scratch,” and it’s clear that she takes this promise seriously. A recent Instagram video highlighted just what this from-scratch promise entailed when it came to this year’s Thanksgiving pies: peeling and cutting 200 apples by hand. This holiday season, however, Fabiana’s is flipping the script: they’ll provide the ingredients, but you’ll be the one making the desserts. Fabiana’s will host a cookie-decorating party from 11am–1pm on December 16, and all participants will walk away with six decorated cookies and the skills to make many more. (Sam Joyce)

Fabiana’s Bakery, 1658 E. 53rd St. Monday–Friday, 7am–7pm; Saturday–Sunday, 8am–5pm. Decorating course $25, cakes starting at $33. (773) 658-9842. fabianasbakery.com

Give Me Some Sugah

When Lenore Lindsey thinks about her childhood, freshly baked cookies and breads come to mind. Those powerful memories inspired her to open Give Me Some Sugah, a made-from-scratch bakery on 71st Street in South Shore that resembles your grandma’s kitchen. She prides herself on using real butter, real sugar, and real eggs to make the neighborhood’s most phenomenal baked goods, even if that means you get a misshapen cookie or lopsided muffin every now and again. The bakery’s famous for its potato chip cookies—a delectable fusion of sweet and salty flavors delivered in a cookie the size of your face—but around the holidays Lindsey recommends her lemon curd scones. “They’re soft, rich and guaranteed to change your opinion of scones forever,” she said. (Carly Graf)

Give Me Some Sugah, 2234 E. 71st St. Monday–Wednesday, 3pm–7pm; Thursday–Saturday, 10am–7pm. $1.50–$75. (773) 363-9330. facebook.com/GiveMeSomeSugah71

Tous Les Jours

If you’re tired of bringing the same old desserts to the holiday party each year, hop over to Tous Les Jours, the “French-Asian” bakery where you’re more likely to find green tea macarons or donuts with red bean filling than sugar cookies and fruitcake. Better yet, get one of the cream cakes, light in weight but rich in flavor. The delicate Green Tea Chiffon Cake ($33–$40) goes nicely with a hot mug of tea, while the more traditional Chocolate Stripe Fresh Cream Cake ($33-$40), embedded with thin slices of strawberry that add some brightness to the cake’s creamy chocolate, is best enjoyed solo on an exceptionally cold day. But if you want to be the talk of said holiday party, show up with the Sweet Potato Mousse Cake ($32-$40). It’s topped with a slice of dried sweet potato and has a flavor that lives up to its name, a unique dessert as fun as it’s delicious. (Tammy Xu)

Tous Les Jours, 2144 S. Archer Ave. Open daily, 9am–10pm. $1–$40. (312) 225-8488. tljus.com

The Medici

I have a Med bakery order for every season: in the summer, it’s a strawberry lemonade and a veggie sandwich (salsa cream cheese, sprouts, tomato, cucumber, and red onion), wrapped to go so I can tuck it into my bike basket as I make my way to a day of sunbathing at the Point. In the fall, it’s a bowl of steaming grilled veggie chili and a side of french fries, which you have to dunk in the chili for the full experience. And my holiday season isn’t complete without their chocolate chip pecan pie, paired with a cup of Mexicana hot chocolate. Underneath the pie crust is a decadent, creamy custard that complements the crunch of the pecans and the chocolate chips so well that you probably shouldn’t promise to share with friends and family—you’ll be tempted to finish the pie off yourself. (Rachel Kim)

The Medici on 57th, 1327 E. 57th St., Monday–Thursday, 7am–11pm; Friday–Saturday, 7am–midnight; Sunday, 8am–11pm. (773) 667-7394. medici57.com

Jimmy Jamm Sweet Potato Pies

This holiday season, give your friends and family the gift of the ever-versatile sweet potato by visiting Jimmy Jamm in Beverly. Here, the sweet potato comes in many forms, including loaded like a baked potato—but for the holidays, it’s all about the pie. When I go, I never buy just one slice of sweet potato pie for myself—I buy at least three full pies to share (and of course pick up a copy of the Weekly lovingly nestled on a shelf). Ask for a sweet potato pie topped with honey cream cheese frosting, which they freshly spread on for you, and admire the eclectic artwork on the store walls as you wait. (Rachel Kim)

Jimmy Jamm Sweet Potato Pies, 1844 W. 95th St. Monday–Saturday, 10am–7pm. (773) 779-9105. facebook.com/jimmyjammpies

Chiu Quon Bakery and Dim Sum

There is nothing like the smell of fresh pastries. In the heart of Chinatown, you will find a very popular and quaint Chinese bakery.  Try one of their many sweet and savory buns, egg tarts, or made-to-order cakes. The sweet bun with bean paste is about the size of a burger. It has just the right amount of bean paste filling, along with a sweet drizzle on top of the bun. A few sesame seeds sprinkled for a final tasty finish. A buttered flaky crust cradles  the Portuguese–style milk egg tart’s soft and fluffy center. This is a small, light treat, good after a meal of any size. The tiramisu cake is a light and decadent pastry that melts in your mouth. Order a slice for yourself or entire cake to share. Whatever your desires, pick up one—or all three—of these recommended tasty treats at Chi Quon Bakery and Dim Sum. You won’t be disappointed by the taste or price. (Maple Joy)

Chiu Quon Bakery and Dim Sum, 2252 S. Wentworth Ave. 7am–10pm. (312) 225-6608. cqbakery.com