Best Sicilian Restaurants in South Side

16 restaurants available nearby

1. Acanto

4.8

Exceptional(3822)

Price: Expensive

• Sicilian • Downtown / Loop

Booked 40 times today

Nestled in the vibrant heart of Downtown Chicago's Loop, Acanto Restaurant + Wine Bar offers an exceptional Wine Bar experience that is a cut above the rest. Celebrated for its "dynamic wine program" that has earned a 3-star rating from World of Fine Wine and a two-glass “Best of Excellence” rating by Wine Spectator, Acanto is the go-to destination for wine aficionados. Patrons rave about the extensive selection, with one guest praising "the best pasta sauce imaginable," and another emphasizing the "perfect pairing" of their wine choice with the delectable Italian dishes. The ambiance is described as "perfect for a date night," making Acanto a must-visit for those seeking an authentic and sophisticated dining experience right across from Millennium Park. Whether it's for a casual happy hour or a refined dinner, the combination of exquisite wines and seasonally-driven Italian cuisine ensures a memorable outing.

2. The Florentine

4.4

Awesome(1297)

Price: Expensive

• Sicilian • Downtown / Loop

Booked 20 times today

Nestled in the heart of Chicago's vibrant Loop Financial district within the JW Marriott, The Florentine stands out as a paragon of Contemporary Italian cuisine. Its menu, celebrated for its simplicity and emphasis on superior ingredients, features top-notch imported Italian pastas, cheeses, salts, and meats alongside finely sourced local farm produce. Patrons consistently praise its offerings, with one noting, “The grilled octopus appetizer was FANTASTIC!” and another lauding the “absolute quality service, food, and libations.” Whether it's for an intimate dinner or a large gathering, The Florentine delivers an exquisite dining experience that captures the essence of authentic Italian fare with a modern twist.

A photo of Connie's Pizza in Bridgeport restaurant

3. Connie's Pizza in Bridgeport

4.7

Exceptional(725)

Price: Moderate

• Sicilian • South Loop

Booked 23 times today

Connie's Pizza in Bridgeport, nestled in Chicago's South Loop, is a true gem for authentic Pizza Bar cuisine. Renowned for its mouthwatering deep dish pizza, Connie's has been hailed as "the best pizza in Chicago" by avid diners. Each pizza, praised for its "divine" taste, is crafted from age-old recipes and baked to perfection, offering a true slice of Chicago right on your plate. The atmosphere is consistently described as great for families and large groups, with a warm, inviting vibe perfect for any gathering. As one reviewer raved, it's a place where the service is as excellent as the food, making every dining experience memorable. Whether it's the iconic deep dish or the innovative Italian Beef pizza, Connie's Pizza promises an unbeatable combination of delicious food and a welcoming environment, making it a must-visit for anyone craving authentic Chicago pizza.

A photo of Paisans Pizza - South Loop restaurant

4. Paisans Pizza - South Loop

4.2

Awesome(51)

Price: Moderate

• Sicilian • South Loop

Booked 8 times today

At Paisans Pizza in the vibrant South Loop of Chicago, the spirit of authentic American cuisine, particularly Chicago-style pizza, is celebrated with gusto. Established in 1985, this family-run gem has perfected the art of pizza-making, boasting "the best pizza place in Chicago," according to thrilled customers. Patrons rave about their award-winning, thin-crust pizzas, highlighting the perfect balance of sauce and cheese as "really enjoyable." Not only is the food consistently lauded, but the ambiance and staff also receive top marks for creating a welcoming and fun atmosphere. Visitors particularly commend the service, describing it as "top-notch" and staff like Esbin and Marino make guests "feel like a regular" with their warm hospitality and attentiveness. Whether it's the "amazing" calamari or the crisp, delightful wings, every dish at Paisans Pizza promises a memorable dining experience in the heart of Chicago's culinary scene.

5. Ummo

4.3

Awesome(469)

Price: Moderate

• Sicilian • River North (Chicago)

Booked 48 times today

UMMO is a contemporary Italian restaurant that unlocks the vibrant flavors of regional Italian cuisine in a colorful, beautifully imagined space.At UMMO, we present contemporary Italian cuisine that seamlessly combines his passion for Italian and American cultures. With a focus on simplicity and quality ingredients sourced from around the globe, UMMO offers fine, house-made pastas, decadent cheese and meat selections, vibrant vegetables, hearty proteins, delicate seafood, and more. As the menu changes frequently to reflect seasonal and new discoveries, guests can experience the full breadth of what Italy has to offer.Join us at UMMO for an unforgettable culinary journey.

A photo of Quartino - Chicago restaurant

6. Quartino - Chicago

4.5

Awesome(10910)

Price: Moderate

• Sicilian • River North (Chicago)

Booked 158 times today

Quartino Ristorante in Chicago's bustling River North neighborhood is a gem for authentic Italian pizzeria cuisine. Known for its Neapolitan thin-crust pizza, the restaurant offers a slice of Italy with every bite, emphasizing the use of traditional techniques and high-quality ingredients. Diners rave about the experience, noting the pizza as a standout dish, with one review highlighting, "Pizza always is great and chocolate cake for birthday dessert was spectacular!" Quartino's vibrant atmosphere and shared plate concept make it perfect for those looking to enjoy a slice in good company. Its consistent praise for delicious, authentic food and inviting ambiance makes it a must-visit for anyone craving exceptional Italian fare in Chicago.

7. Formento's

4.7

Exceptional(2815)

Price: Expensive

• Sicilian • West Loop

Booked 49 times today

Situated in the vibrant West Loop of Chicago, Formento's is a treasure trove of Italian culinary delight, offering a heartfelt homage to traditional Italian cuisine with a modern twist. With house-made pastas and wood-fired entrees, each dish showcases the brightness and freshness of authentic Italian flavors. The restaurant’s dedication to quality is evident, with rave reviews like, "You've never had real Olive Oil until you've tasted this one," highlighting the meticulous care in sourcing ingredients. Formento's not only promises an exceptional dining experience with its extensive wine selection of over 300 varietals but also ensures a memorable visit with its impeccable service and welcoming atmosphere. Whether it's the Carbonara, the Vodka pasta, or the unique Black Squid Pasta, Formento's stands out as a must-visit for anyone craving genuine Italian in Chicago.

8. Mart Anthony's

4.8

Exceptional(1662)

Price: Moderate

• Sicilian • West Loop

Booked 32 times today

Mart Anthony's in Chicago's vibrant West Loop is a beacon of classic Italian cuisine, where every dish tells a story of family heritage and culinary passion. This third-generation restaurant charms locals and visitors alike with its "phenomenal food" and "friendly atmosphere." Patrons rave about the authenticity and quality of dishes like the Stuffed Artichoke and Tortellini Romano, describing them as "always delicious." A standout feature noted in reviews is the warm, attentive service and the cozy, inviting ambiance, making every meal memorable. As one diner puts it, Mart Anthony's is "by far the best Sicilian restaurant in the Midwest," a testament to its unwavering excellence and authenticity in Italian dining. Whether you're a first-timer or a long-time fan, Mart Anthony's promises an "amazing" Italian experience.

A photo of Olio e Più - Chicago restaurant

9. Olio e Più - Chicago

4.6

Exceptional(905)

Price: Expensive

• Sicilian • River North (Chicago)

Booked 93 times today

OLIO E PIÙ brings Italian tradition and true sense of Mediterranean liveliness to the vibrant neighborhood in Chicago.As an authentic trattoria, its cuisine is based on classic Italian dishes. As you dine at OLIO E PIÙ, you’ll be transported not just by the flavors of Italy but also by the authentic atmosphere that surrounds you. It’s a place where time slows down, and conversations flow freely, just as they do in a true Italian household. Here, the spirit of 1970s Italian elegance lives on, and every meal is a celebration of life, love, and the joy of shared moments, especially with the open kitchen concept.OLIO E PIÙ is more than just a restaurant; it’s a portal to a different time and place, where the essence of Italy’s rich culinary and cultural heritage is captured in every detail.

A photo of Professor Pizza - Old Town restaurant

10. Professor Pizza - Old Town

4.4

Awesome(109)

Price: Expensive

• Sicilian • Old Town

Booked 36 times today

Professor Pizza in Old Town, Chicago, has quickly become a beacon of pizzeria excellence, celebrated for its unique and authentic Italian-American offerings. The restaurant’s diverse menu, featuring Chef Tony Scardino’s signature pizzas, has diners raving about the "closest thing I’ve had to a true NY slice in Chicago." With a variety of crusts, including gluten-free options and innovative toppings, every pizza is a masterpiece. The Grandma-style crust is particularly lauded for its crispy yet chewy texture, earning high praise as "the ultimate dissertation of pizza." Coupled with a lively atmosphere and stellar service, Professor Pizza is hailed as the "best pizza in Chicago," making it a must-visit for both locals and tourists alike. Whether it’s the NY White Pie that tantalizes or the mozzarella onion rings that delight, this spot is an unforgettable culinary gem in the heart of Old Town.

‘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.

Explore OpenTable

South Side

Sicilian

Best Sicilian Restaurants in South Side

Price

Regions

Areas

Top Rated

Dining Options

Seating options

Accessibility

16 restaurants available nearby

1. Acanto

2. The Florentine

3. Connie's Pizza in Bridgeport

4. Paisans Pizza - South Loop

5. Ummo

6. Quartino - Chicago

7. Formento's

8. Mart Anthony's

9. Olio e Più - Chicago

10. Professor Pizza - Old Town

Explore OpenTable