Chicago’s Coziest Restaurants to Hibernate in Before Winter Ends
via Crosby’s Kitchen
Each year, when Chicagoans aim to survive the depths of winter, the list of appealing outdoor plans shrinks fast. That's when the city's legendary hospitality truly shines, wrapping us in a welcoming array of cozy dining escapes that chase away the chill.
Here are some inviting spots to discover (or revisit) this season—your new favorite winter hideaway is waiting!
Crosby's Kitchen {3455 North Southport Avenue, Chicago, IL; 773.883.2525}
Another gem tucked away on a charming neighborhood corner, Crosby’s Kitchen sits in the heart of the Southport Corridor and is the perfect spot for a family outing or a casual dinner with friends. With a menu designed to satisfy every craving, it’s easy to see why this neighborhood favorite draws such a loyal crowd. Weeknight specials make it an ideal go-to for busy evenings, while the welcoming atmosphere sets the scene for relaxed family dinners. Pair your hearty entrée with a glass from their impressive wine selection, and you’ve got a meal worth savoring.
Highlights include:
Wrightwood Salad: Rotisserie chicken, tomatoes, craisins, avocado, corn, almonds, cornbread croutons, roasted red peppers, scallions, goat cheese, citrus vinaigrette
Black Bean Chicken Chili: Saturday and Sunday special, served with tortilla chips
Steak Frites: Grilled bistro steak, au poivre sauce, French fries, garlic aioli
via Dimmi Dimmi
Dimmi Dimmi {1112 West Armitage Avenue, Chicago, IL; 773.697.9829}
Nestled on the corner of Seminary and Armitage sits one of Lincoln Park’s coziest Italian gems. It may be tough to snag a reservation at Dimmi Dimmi, but it’s more than worth the wait—especially if you’re a fan of cracker-crust pizza. If you’re lucky enough to score a table, you’ll be rewarded with a menu full of legendary comfort dishes that live up to the hype. Reservations drop on the first of every month, but the restaurant always saves room for walk-ins. With something for everyone—even the pickiest eaters—Dimmi Dimmi is the perfect place to cozy up on a Saturday night during these harsh winter days. Trust us, you’ll want to try it for yourself.
Highlights include:
Sesame Focaccia: Served with Olio Verde olive oil. Add a side of ricotta & honey, tomato nduja, or creme di fagioli
Vodka Pizza: Vodka sauce, sweet onions, nduja, calabrian chili, cheese blend
The Press Room {1134 West Washington Boulevard, Chicago, IL; 312.450.3301}
Located in Chicago’s West Loop, this wine and cocktail bar offers an elegant yet welcoming dining experience. The Press Room’s menu is filled with savory seafood dishes, so there’s no need to wait until summer to enjoy those bright, coastal flavors. Treat yourself to a few small bites from their irresistible charcuterie selections — perfect for sharing. You’ll also be impressed by their extensive cocktail and wine list, showcasing everything from bone-dry pours to delightfully sweet sips. Ball on a budget with a $10 glass of wine during happy hour, available Tuesday through Thursday from 4–6 pm. So swap those slippers for some booties and head out to savor the cozy, memorable moments The Press Room brings this winter.
Highlights include:
PB&J Bites: Poached pear, brie, jambon de Paris served on a crostini with mostarda
Cheese & Charcuterie: Spicy calabrese | Italy
Denucci's {503 West Dickens Avenue, Chicago, IL; 773.697.8780}
This charming Italian-American joint is full of warmth and character. Tucked away in the heart of Lincoln Park, Denucci’s has everything you need to cozy up on a cold night. While the atmosphere feels delightfully traditional, the menu encourages you to step outside the classics and try something new. Generous portions make it perfect for sharing. Reservations are a smart move on weekends, but it’s just as lovely for a relaxed weekday dinner.
Highlights include:
Lumache alla Vodka: Add on crumbled sausage for $4
Chicago Tavern-Style Pizza: Monday special
via Asador Bastian
Asador Bastian {214 West Erie Street, Chicago, IL; 312.800.8935}
This Spanish steakhouse takes grilling to the next level, showcasing unique cuts of meat with remarkable marbling, expert technique, and stunning presentation. Guests can choose between the Bar Room and the Dining Room, each offering a distinct atmosphere and its own irresistible menu. Whether you’re planning an intimate date night or a celebratory dinner with friends, Asador Bastian strikes the perfect balance between romance and energy.
Highlights include:
Turbot al Pil-Pil: With lemon and parsley
The San Miguel: Hand-cut bone-in steak under 1lb
Punch House Chicago {1227 West 18th Street, Chicago, IL; 312.526.3851}
This historic hideaway tucked beneath Thalia Hall is truly one of a kind. With a cocktail menu inspired by 17th-century sailors, five tenets of quality, and thoughtfully curated food pairings, Punch House offers an experience unlike any other.
Its modernized mid-century aesthetic instantly melts away your Chicago winter worries. If you’re craving a little excitement this weekend, head to Punch House Chicago and indulge in the art of mixology, music, and dance.
Highlights include:
Passion Burn: Green chili vodka, passionfruit liqueur, honey, elderflower, lavender, lime
Chicago Punch: Malort, elderflower, rosemary peach tea, Mexican cinnamon syrup, grapefruit
Twin Anchors {1655 North Sedgwick Street, Chicago, IL; 312.266.1616}
An oldie but a true classic — and home to ribs you won’t soon forget. If you love that timeless Chicago charm, Twin Anchors is a must-visit. This historic spot has been creating memories since 1932, and you can feel that history the moment you step inside. Tucked into a cozy corner with a slab of ribs in front of you, you’re surrounded by the spirit of old Chicago. It’s the perfect place to bring your parents or a friend visiting from out of town, thanks to its warm atmosphere and undeniable sense of tradition.
Highlights include:
Cheese Anchor Burger: 1/2lb pure Angus beef served on a soft roll with a choice of American, Swiss, Cheddar, or Pepper Jack cheese served with lettuce and tomato
World Famous Ribs: Slow-cooked, meaty, and tender. Basted with your choice of sauce
via The Loyalist
The Loyalist {177 North Ada Street, Chicago, IL; 773.913.3774}
Hidden beneath the two–Michelin-starred Smyth is its charming sister restaurant, The Loyalist. This gem checks every box for the ultimate cozy vibe, set in a dimly lit basement that feels instantly inviting. Sink into one of their plush booths, order the OG Burger, and you’re all set — you might even forget you’re in a restaurant and not curled up on your favorite couch at home. Whether you’re in the mood for a boozy brunch with friends or planning a special dinner with an old friend, The Loyalist fits any occasion.
Highlights include:
The Loyalist OG Cheeseburger: Pickled & charred onion, sesame seed bun, frites
Bistro Filet: Madeira jus and anchovy butter
Quiche Lorraine: Benton's bacon, leeks, gruyère, truffle vinaigrette
Gilt Bar {230 West Kinzie Street, Chicago, IL; 312.464.9544}
This restaurant is a great place to visit any time of year, but it’s especially enticing for Chicagoans braving those brutal winters. After all, who wouldn’t want to spend an evening tucked into a circular velvet booth, indulging in the ultimate lineup of comfort dishes? With its effortless embrace of old-money elegance, this spot feels like a step back into a more glamorous era. It would be a shame not to experience it for yourself.
Highlights include:
Tagliatelle Carbonara: Guanciale, egg yolk confit, gorgonzola
Coal-Fired Ribeye: 16 oz center cut, USDA Prime, herbed bone marrow
By Eleanore Adam | Special Correspondent