Michael Dorf stood with his brother Josh, smiling over the barrel filled with wine from grapes they'd just crushed, fermented, and pressed. He claims that despite tastings and classes, he'd never begun to understand wine until this moment. As his understanding grew, he laid the foundations for City Winery: a full winery facility, restaurant, and concert venue inside urban Chicago. He now watches over more than 400 international wines and 20 house wines. Inside the winery, these wines—made from nine US and international varietals—age inside stainless steel tanks and American and French oak barrels. Here, staffers lead winemaking classes, letting visitors join the crushing and fermenting process, and showing them how make private barrels and fill custom juice boxes or bottles pasted with labels of their own design.
These monolithic tanks and barrels can be seen through floor-to-ceiling windows from most of the restaurant's rooms, where servers ferry Executive Chef Andres Barrera's dishes, each a blend of Italian, French, Spanish, and Middle-Eastern flavors. The culinary team crafts small and large plates of artisanal cheeses, seafood, and flatbreads—which they make using the winery's own wine lees as yeast. In the restaurant and Barrel Room tasting bar, staffers pour housemade wines piped fresh from the cellar through 14 taps, while visitors bask in the glow from hard wood and floor to ceiling windows. Patrons dine on a ground floor lit by soft blue lights and hanging lamps fashioned from old wine bottles, as well as a mezzanine level looking out on the city skyline. Private dining rooms gather guests around long communal tables, stretched between exposed brick walls. In the show venue, comedians, live musicians, and slapstick-prone stage crew members entertain audiences under the glow of tabletop candles.
Naturally, the chefs at Cooper’s Hawk have a sharp eye when it comes to wine pairings. Each of the restaurant’s contemporary dishes is crafted with a particular wine in mind, which makes plenty of sense given the fact that there’s a winery located just next door. Surrounded by oaken barrels and racks lined with glistening bottles, diners may be forgiven for thinking that they made a wrong turn and ended up in the winery itself. After your meal, see the real thing in the Napa–style tasting room, where you can sample up to eight different wines. The selection includes something for everyone, including graceful blush wines and cabernets whose flavors unfold like a novel scribbled on the wings of an origami crane.
To find many of the fresh fruits, vegetables, and herbs that underscore their Mediterranean menu, Autre Monde Cafe & Spirits' chefs only need to walk a few steps away from the kitchen?to the restaurant's own greenhouse. Although it's hard to get more local than that, many other ingredients are sourced from Cakeridge Farms in the Ohio River Valley, owned by head chefs Dan Pancake and Beth Partridge. Both worked under James Beard Award winner Tony Mantuano in Chicago before perfecting their Mediterranean cooking and wine-bottle-juggling on Spain's Costa Brava.
At Autre Monde Cafe & Spirits, Dan and Beth whip up fresh pasta, flatbreads made to order, and small plates inspired by French, Spanish, and Moroccan cuisine. A lengthy wine and spirits menu makes it easy to pair each dish with an apropos beverage, including small-batch and organic options. Diners can enjoy their meal on the restaurant's three-season patio or inside at tables crafted from fallen ash trees harvested from Cakeridge Farms.
The experts at Wine Discount Center taste wine like it’s their job—because it is, actually. Every month, they taste hundreds of wines, assessing each one’s color, aroma, flavor, body, knowledge of American history, and finish in the same manner that the critics of Wine Spectator and Wine Advocate use to grade wines on their 100-point scales. This never-ending sampling and scoring lets Wine Discount Center’s team continually update and hone the selection at each location, regularly announcing new finds on the company's website and ensuring each bottle it stocks is worthy of 85 points or more. The oenophiles further enhance guests’ enjoyment of their wines by leading in-store tastings every Saturday at noon.
Organic and small-batch wines fill swirling glasses beneath the soaring ceilings of House Red Vinoteca. At a rustic, reclaimed-wood bar, discerning staff members subject new elixirs to tastings and credit checks, and the chef makes changes to a rotating menu of vino-enhancing fare made from scratch. Plates bearing crispy flatbreads and desserts inspired by international culinary traditions glide back and forth between duos chattering beneath exposed-brick walls. The warm sway of live jazz rolls across wine-tasting events and bottle-laden shelves, and patrons sipping through tasting flights from Croatia, Lebanon, Morocco, Serbia, and Slovenia add delicate treble notes with clinking glasses.
At Chalk, craft beer reins supreme with more than 25 taps containing primarily local pours such as Revolution, Lagunitas, and Three Floyd's. Besides brews, nearly 25 [bourbons](http://gr.pn/1oS5xEy and Irish whiskeys line the bar, which can satisfy thirsts as patrons watch games on flat-screen TVs or stare blankly at exposed-brick walls. Each libation complements Chalk's faithful take on pub classics, from mac-n-cheese bites to onion rings battered in stout. Then, of course, there are chicken wings, which chefs serve in batches of up to 20 slathered in a choice of more than five sauces, including Jamaican jerk.