Best Upscale Italian Restaurants in Old Town | Upscale Italian Food

8 restaurants in Best Upscale Italian Restaurants in Old Town | Upscale Italian Food

• Topo Gigio Ristorante — Italian: This vibrant Old Town landmark hums with the spirited energy of clinking wine glasses and lively conversation, drawing guests into a space that feels like a timeless neighborhood embrace. Sun-dappled afternoons on the lush garden patio transition into intimate evenings filled with the intoxicating aroma of roasted garlic and simmering sauces. Every plate of al dente pasta and classic Italian fare celebrates the joy of communal dining, offering a soulful experience where every meal feels like a festive occasion.
• Happy Camper Old Town — Italian: Step into a whimsical wonderland where neon lights and disco balls illuminate a nostalgic space filled with vintage trailers and tire swings, creating a perpetual summer camp vibe. The air buzzes with high-energy charm as guests gather to share creative, thin-crust pizzas and boozy cocktails, making every meal feel like a vibrant backyard party in the heart of the city.
• Gallucci Pizzeria Napoletana — Italian: The air at Gallucci Pizzeria Napoletana is thick with the scent of toasted flour and melting buffalo mozzarella, drawing guests toward the golden glow of a roaring wood-fired oven. Here, the art of the pizzaiolo takes center stage as hand-stretched dough is transformed into blistered, leopard-spotted masterpieces topped with vibrant San Marzano tomatoes and fragrant, garden-fresh basil. It is a lively, soul-warming sanctuary where the rustic charm of Naples meets a contemporary energy, making every meal feel like a spirited Italian celebration.
• Pazza Pizza — Italian: Flour-dusted counters and the roar of a stone oven set the stage at this vibrant neighborhood haunt, where the air is thick with the scent of bubbling mozzarella and toasted garlic. Artisanal pies emerge with perfectly charred, blistered crusts, topped with bold combinations that balance classic tradition with a spirited, modern flair. It’s a place where the energy is as infectious as the food, inviting guests to linger over a cold craft beer and a slice of something truly exceptional.
• La Storia — Italian: Stepping into La Storia feels like entering a cherished family archive, where flickering candlelight dances across exposed brick walls and the air is thick with the comforting scent of slow-simmered ragù. Each plate serves as a soulful chapter of culinary heritage, bringing together hand-kneaded pastas and sun-drenched ingredients that celebrate the timeless art of the long, lingering meal. It is a sanctuary of storytelling where the rhythmic clinking of wine glasses and the warmth of genuine hospitality turn every dinner into a lasting memory.
• Carmine's — Italian: Step into a boisterous, high-energy hall where the air is thick with the intoxicating scent of roasted garlic and the joyful clamor of shared celebrations. Massive platters of classic Italian-American comfort food are passed around crowded tables, inviting guests to dive into towering mounds of saucy pasta and golden-crusted chicken parmigiana. It is a place where the spirit of the Sunday family dinner is elevated to a grand scale, turning every meal into a festive and communal feast.
• Lou Malnati's Pizzeria — Italian: Step into a bustling Chicago landmark where the irresistible aroma of golden, buttery crust and simmering tomato sauce fills the air. Each legendary deep-dish pizza is a masterpiece of layers, featuring a flaky, hand-pressed base topped with savory sausage and vine-ripened tomatoes that melt into a rich, gooey center of Wisconsin mozzarella. The lively, unpretentious atmosphere invites friends and families to gather around seasoned pans for a quintessential taste of the Windy City that feels both nostalgic and timeless.
• Orso's — Italian: Stepping into this ivy-clad sanctuary feels like discovering a hidden corner of old-world Italy, where a lush, twinkling garden patio offers a romantic escape from the urban bustle. The air is perfumed with the scent of simmering garlic and fresh basil as guests linger over plates of velvety handmade pasta and classic regional favorites, all served with a timeless warmth that transforms a simple meal into a storied neighborhood tradition.