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Best Italian Restaurants in South Side

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122 restaurants available nearby

A photo of Alla Vita restaurant
1. Alla Vita
4.8
Exceptional(2425)
Price: Expensive
• Italian • West Loop
Booked 177 times today
Alla Vita, located in the vibrant West Loop of Chicago, offers an exceptional Italian dining experience that truly stands out. Executive Chef Lee Wolen masterfully creates dishes using the finest ingredients, delivering "fresh, flavorful, and every bite better than the last." Guests rave about the delicious ricotta dumplings and vodka pasta, describing the food as "absolutely fabulous." The wood-fired table bread is a must-try, providing a "pillowy and delicious" start to any meal. The restaurant's warm, inviting atmosphere and attentive service make it a perfect spot for any occasion, ensuring Alla Vita "never fails to impress" its diners.
A photo of Franco's Ristorante restaurant
2. Franco's Ristorante
4.9
Exceptional(665)
Price: Moderate
• Italian • Bridgeport
Booked 6 times today
If your preferred time is unavailable please call for possible openings. Franco's Ristorante is the perfect combination of old world Italian classics and your new favorite pasta dishes. We've been around for over 27 years and have perfected our craft. Some of our most famous dishes include whipped ricotta tuffo, sausage and peppers, eggplant parmigiana and gnocchi. Our great food and atmosphere helped us earn the honor of being named the Chicago Reader's 2016 "best place for a cheap date" and "best local restaurant." You will be wowed when you step inside our bright, airy and modern restaurant. You can enjoy a drink at our new marble-topped bar or cozy up to tables with bright red-leather chairs and banquettes in the dining room. In the summer we are happy to offer outdoor seating that allows dogs.
A photo of Il Culaccino restaurant
3. Il Culaccino
4.3
Awesome(1096)
Price: Moderate
• Italian • South Loop
Booked 13 times today
If your preferred time is unavailable please call for possible openings. Il Culaccino, the new fine Italian dining restaurant presented by the Franco’s Restaurant Group, comes to McCormick Square in Spring 2019. Anchored in the Arrive Lex Apartment Tower, 2134 South Indiana, Il Culaccino is just steps away from Wintrust Arena and a short walk from McCormick Place. At Il Culaccino, you’ll enjoy unique wines and delicious plates accompanied by the friendly and superior service that has become the hallmark of Franco’s Restaurant Group, family-owned since 1989.Be prepared to have your senses thrilled at Il Culaccino, before or after exploring McCormick Square, Chicago’s most exciting and vibrant new entertainment district.
A photo of Dolce Arte - The Art of Food restaurant
4. Dolce Arte - The Art of Food
4.7
Exceptional(19)
Price: Moderate
• Italian • Bridgeport
Booked 2 times today
Dolce Arte - The Art of Food is a Café delight nestled in the heart of Bridgeport, Chicago, offering a genuine taste of Italy with every bite. Renowned for its "phenomenal food" and "impeccable service," this cozy café invites you to indulge in a variety of freshly baked Italian pastries and the finest LavAzza coffee. Diners rave about the "best American pancakes" and the exquisite pasta paired with Antinori wine, making each meal a memorable experience. Whether you're there for breakfast, lunch, or dinner, Dolce Arte promises an "outstanding dining experience" that will have you eagerly planning your next visit.
A photo of Acanto restaurant
5. Acanto
4.8
Exceptional(3937)
Price: Expensive
• Italian • Downtown / Loop
Booked 67 times today
Acanto Restaurant + Wine Bar, located in the vibrant Downtown Loop of Chicago, is a haven for wine enthusiasts and Italian cuisine lovers alike. This esteemed establishment boasts one of the most revered wine programs in the U.S., earning a prestigious three-star rating by World of Fine Wine and a two-glass "Best of Excellence" rating by Wine Spectator. Visitors rave about the "fabulous wine selection" and "knowledgeable sommelier" who enhance the dining experience with passionate recommendations. The cozy, conversation-friendly atmosphere paired with an exceptional array of Italian classics and craft cocktails ensures that Acanto is a must-visit destination for any wine lover.
A photo of Connie's Pizza in Bridgeport restaurant
6. Connie's Pizza in Bridgeport
4.6
Exceptional(756)
Price: Moderate
• Italian • South Loop
Booked 13 times today
Connie's Pizza in Bridgeport is a cherished gem for Pizza Bar aficionados seeking authentic and delectable pizza in Chicago's South Loop. Known for its "delicious, perfectly cooked" pizzas that are "packed with flavor," Connie's consistently wins hearts and taste buds alike. Diners rave about the "great atmosphere" and "excellent service" that complement the outstanding culinary offerings. From classic Chicago deep-dish to flavorful sausage pizzas, every dish is a testament to Connie's commitment to quality. With a spacious dining area perfect for large gatherings and a menu that delights, Connie's Pizza is an essential stop for both locals and visitors.
A photo of The Florentine restaurant
7. The Florentine
4.4
Awesome(1313)
Price: Expensive
• Italian • Downtown / Loop
Booked 29 times today
The Florentine, nestled in the heart of Chicago's vibrant Loop Financial district at the JW Marriott, is a hidden gem for Contemporary Italian cuisine. With a menu that artfully balances simplicity and quality, it features top-notch imported Italian pastas, cheeses, and meats alongside local farm ingredients. Diners rave about the "fantastic grilled octopus appetizer" and the "wonderfully fresh, delicious, and well-seasoned entrees." The restaurant's ambiance is both elegant and warm, providing an ideal setting for intimate dinners or lively group gatherings. The Florentine's attentive service and culinary excellence make it a must-visit destination for Italian food enthusiasts.
A photo of Sofi Restaurant restaurant
8. Sofi Restaurant
4.7
Exceptional(1690)
Price: Expensive
• Italian • South Loop
Booked 8 times today
Nestled in the vibrant South Loop of Chicago, Sofi Restaurant is a beacon of exquisite Seafood cuisine, celebrated for its authentic Italian flavors. Chef Maurizio Michi's mastery is evident in dishes like the Fish Stew Viareggina, which reviewers rave is "as close to a real Italian one as I've had out of Italy." The meticulously prepared grilled Sea Bass Branzino and succulent baby octopus are standout offerings that underscore Sofi's commitment to quality. Diners praise the "fantastic food, service, and ambiance," making Sofi not just a meal, but a memorable experience. For an authentic taste of the sea, Sofi is unmatched.
A photo of Peanut Park Trattoria restaurant
9. Peanut Park Trattoria
4.8
Exceptional(255)
Price: Expensive
• Italian • Little Italy / University Village
Booked 10 times today
Peanut Park Trattoria, nestled in the vibrant Little Italy of Chicago, is your ultimate destination for exquisite Pizza Bar cuisine. Known for its authentic Italian flavors, this charming spot has been celebrated as "One of the Absolute Best Italian Restaurants in Chicago" by Tasting Table. The pizza here is a standout, described as "piping hot, nicely fresher, and delicious," making it a crowd favorite. The restaurant's commitment to quality is evident, with diners raving about the "great food, cocktails and service" that create a warm and inviting atmosphere. Perfect for any occasion, Peanut Park promises an unforgettable dining experience.
A photo of Tuscany on Taylor restaurant
10. Tuscany on Taylor
4.8
Exceptional(2241)
Price: Moderate
• Italian • Little Italy / University Village
Booked 10 times today
Tuscany on Taylor is the original Tuscany restaurant opened in 1990 in the heart of Little Italy. A comfortable trattoria, Tuscany serves Northern Italian favorites including: homemade pastas, pizzas from our wood-burning ovens, signature Italian chicken dishes, grilled veal and other authentic dishes. Private party space available.
‘About the restaurant’ descriptions have been generated using an artificial intelligence model comprised of OpenTable proprietary data that has not been independently verified by OpenTable. The content is presented as-is, for informational purposes only.

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