Chicago’s Essential Cozy Locales

If we could dine outside all year long at The Duck Inn, on the bi-level patio with its copious foliage, we would. But this is Chicago and, well, winter happens. Never mind: head inside to the boisterous front bar or the intimate dining room instead. With exposed brick, dark wood tables, soft lighting, and a view into the open kitchen, this Michelin Bib Gourmand-recognized gastro-tavern from chef Kevin Hickey and beverage director Brandon Phillips is a true neighborhood gem. Start with smaller dishes like the braised octopus with fingerling potatoes or butternut squash agnolotti; then move on to signature duck items like the Chicago-style duck dog with duck fat fries, or the star of the show: Hickey’s rotisserie duck with duck fat potatoes, Mick Klug peaches, duck jus, and more.

Chef Sangtae Park and his wife, Kate, gained acclaim with their intimate Michelin-starred six-seat Omakase Yume, but if you’re not feeling quite so splurge-y, you can still get a taste of super fresh, high-quality sushi at their adjacent TenGoku Aburiya izakaya. On offer is an array of nigiri, sashimi, and signature rolls, but also ramen, udon, kushiyaki, donburi, chicken karaage, tempura, and more comforting Japanese snacks. There’s no fireplace, but the hot miso soup and hotter fresh wasabi will warm you right up.

Like hikers seeking refuge from the rugged Swiss Alps in European berghauses, so too can Chicagoans find respite from the elements inside of Table, Donkey and Stick. This cozy Logan Square spot wraps a warm hug around you the moment you step up to its handmade wooden bar, filled with known and esoteric spirits, including various brandies and amaros as well as regional Alpine wines and beer. The food reflects mountain culture – charcuterie and cheese, crispy potato latkes with horseradish, sweet corn risotto, pork schnitzel, and more — equally fitting fare for a tough Chicago winter. 

Set up a flight of stairs at the base of the gilded One Chicago building, Petit Pomeroy is an offshoot of the hugely popular Winnetka spot from Ballyhoo Hospitality. Here, the restaurant features the greatest hits from the suburban spot, including warm crispy baguettes, a flaky warm tomato tarte with fromage blanc, frisée salad with lardons, a lobster roll overflowing in a buttery bun, and filet au poivre. Adding to the coziness are red leather banquettes, warm wood paneling, and views out over the city from wide open windows behind the eight-seat bar, where you can order French-inspired cocktails and a full French wine list.

To call this a boudoir-styled space “sexy” is an understatement. The slatted wood ceiling, plush red velvet booths and banquettes, moody lighting, heavy velvet curtains, high-backed tufted-leather chairs, vintage framed art, and more draw you in, while the food keeps you coming back. (Would you expect anything less from Brendan Sodikoff’s Hogsalt Hospitality?) The menu leans Italian, with garlic and olive focaccia, burrata, and beef-pork-veal meatballs to start, and black truffle bucatini, whole branzino, and a 16-ounce coal-fired ribeye with roasted garlic and rosemary butter to round it out.

Cozy up by the fire during chilly winter nights — in this case, a massive wood-burning oven that commands attention, by design, of course. Think of it as a special ingredient that makes some of Fiya’s most soulful pan-Levantine dishes sing, like the zippy Moroccan fish with red pepper sauce, the khachapuri served two ways, and fluffy pitas made fresh every morning.

Tucked away on the second floor of the historic Chicago Athletic Hotel, Cherry Circle Room goes for upscale cozy, inspired by the lavish atmosphere of ’50s-era supper clubs. With tufted leather banquettes and a wrap-around wooden bar and cabinetry, its design earned a James Beard Award in 2016. Whether you’re dining before a show or making a full night of it, come for dishes like raviolo with truffled pasta, apricot-chile glazed pork ribs, and plenty of classic cocktails to boot.

Whether nestled into the cushioned banquettes or bellying up to the bar, French bistro Obelix, from Poilevey brothers (who also own Bucktown’s Le Bouchon), invites you to kick back and enjoy oysters, wine, and, well, life. Amp your enjoyment with filet mignon steak tartare with a caramelized onion aioli or some of the city’s best French onion soup. Keep it going with a seasonal savory pastry (currently featuring Klug Farm apples, caramelized onions, and raclette cheese), foie gras macarons, or the Obelix Dog, a duck- and foie gras-filled corn dog. Finish things out with côte de boeuf or 10-day dry-aged duck breast with Hakurei turnips, poached apricots, and spiced duck jus. Then pour yourself another glass of Beaujolais and smile as you watch the world bustle by. Need a daytime fix? Obelix is open for lunch Thursday, Friday, and Monday and brunch on weekends.

There’s nothing cozier than a great bar, and a seat by the fireplace at Scofflaw remains one of our favorite spots on a cold night. A warm or spiritous cocktail by the fire is a perfect nightcap, made even better by some excellent bites.

With its heavy retro feel, Club Lucky brings circa 1940-supper club vibes to Wicker Park, where it’s been a neighborhood favorite for decades. Come for classic Italian and American-Italian dishes, from stuffed artichokes and mozzarella fritti to homemade lasagna and bright and crispy veal limone. Or stop by for a drink, including excellent oversized martinis, or novel-inspired cocktails, like The Vesper Lynd (from Casino Royale) with Journeyman gin, Stoli vodka, Lillet Blanc, Fee Brothers orange bitters, and a lemon twist.

For one of the coziest and most romantic rooms in the city, you almost can’t do better than this Lincoln Square gem. The quaint French bistro has kept diners coming back for 20 years with classics like French onion soup, hangar steak frites with Maître d’Hôtel butter, and dark chocolate pot de crème with Chantilly cream. The exposed brick patio comes alive with vibrant flowers, ivy, and twinkling lights that make it feel miles from the city — yet is mere steps off Lincoln Avenue.

Carbs, carbs, and more carbs. Yes, we said it and yes, we want it. Middle Brow Brewing continues to be one of the city’s best spots for all things kneaded and baked. Think brunchy bread and cultured butter service (or add sardines, honey, smoked delicata spread, and more), blueberry buttermilk cake, and shakshuka; and crisp-crusted pizza reminiscent of Napoli (they do tavern style on Tuesdays) topped with everything from housemade sausage and green olives to sungold tomato-bacon jam and potato to wild mushrooms. Their own draft beer and low-intervention wine programs are supplemented by cocktails with local spirits like Judson & Moore, Misoo, and Letherbee. Plus, it’s an all-day affair, so you can cozy up any time. 

With exposed light brick, warm natural woods, walls lined with framed photos, and a bustling corner location, Bar Roma brings a taste of Italy to Andersonville. Think antipasti misto, an array of hearty meatballs, wood-grilled meats and seafood including chicken or eggplant parm, and chef Alfredo Ramos’ handmade pastas like tonnarelli cacio e pepe; gnocchi with sauteed shrimp, leeks, and black truffle; and the warming Nonna’s Lasagna with three kinds of cheese in a mushroom pomodoro sauce — alongside an entirely Italian wine list. 

After more than a year of serving breakfast and lunch to go on their patio, Tim Flores and Genie Kwon finally realized their dream of opening their dining room. With light woods, hanging plants and an open kitchen, this is where Kwon continues her mastery of delicious baked goods and where Flores dazzles Chicago with its first Filipino tasting menu — a $285 multi-course stunner that changes seasonally and can be paired with beverages for $185 (non-alcoholic option available for $95). Since opening, the restaurant has received numerous accolades, including being awarded the world’s first Michelin star for a Filipino restaurant and a James Beard Award for Best New Restaurant and Best Chefs in the Great Lakes region. Note that daytime counter service is first come for items like their craveable longanisa, egg, and cheese breakfast sandwich and Kwon’s array of sweet and savory pastries, like the black truffle croissant, cardamom bun, and foie gras danish. Reservations are required for the evening tasting menu. 

Hogsalt Hospitality scores another hit with this dark and warm Lincoln Park spot that taps into British pub culture, reimagining the gastropub as an everyday neighborhood joint. Find a menu ranging from savory minced spiced lamb pies and chicken tikka masala to steak frites and fish and chips to enjoy, alongside gin and whiskey cocktails, British ales, and a global wine selection. 

The Logan Square O.G. has been the place to go for more than 25 years for hearty, market-driven fare. Chef Jason Hammel and his crew quietly grew a cult following to an understated dining room that features pieces by local artists. Why? Simply put, regulars return for simply prepared, incredibly flavorful plates like smoked trout scramble, blue cornmeal tea cake with sour cherry and mascarpone cream, pasta Yiayia bucatini with feta and brown butter, chickpea and fennel tagine with golden raisins and green harissa, and wagyu bavette steak with sweet potatoes and schmaltz aioli. Pop in for daily happy hour at the bar between 4:30 and 6 p.m. for seasonal crudite with golden beet dip, marinated olives, and Cantabrian anchovy and butter toast. 

Whether it’s getting together with old friends or having a casual family dinner, there’s a reason people continue gathering here after nearly 10 years. The simple yet consistently delicious fare always delivers — whether it’s the bulgogi-glazed barbecue short rib, uovo raviolo with house-cured pancetta, or one of Chicago’s best burgers topped with white cheddar, bacon, and caramelized onions. Pro tip: Request a kitchen counter spot for a truly up-close encounter with the kitchen team. 

Walking into Mi Tocaya, Logan Square’s beloved intimate Mexican spot run by the intrepid Diana Dávila, feels like walking into a special celebration year round. The vibrantly colored space plays the perfect accompaniment so many dishes that pay homage to Davila’s heritage including hand-pressed heirloom corn tortillas, zesty aguachiles, creamy guacamole, cochinita pibil, grilled Spanish octopus, and crab tetela, her “Mexicanized” version of crab Rangoon with heirloom masa stuffed with blue crab, spring onion, queso suizo, and poblano chiles.