Best Sicilian Restaurants in South Side

Price

££
£££
££££

Regions

ChicagoNear WestSouth Suburbs

Areas

BerwynDowntown / LoopGold Coast / StreetervilleOak LawnOld TownRiver North (Chicago)

Top Rated

CharmingGood for business mealsGood for groupsGood for special occasionsGreat for brunchGreat for fine wines

Dining Options

All dining options

Delivery only

Takeaway only

Seating options

BarCounterStandardHigh TopOutdoor

Accessibility

Gender-neutral toiletWheelchair access

15 restaurants available nearby

1. Acanto

4.8

Exceptional(3937)

££££Price: Expensive

• Sicilian • Downtown / Loop

Booked 65 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.

2. The Florentine

4.4

Awesome(1313)

££££Price: Expensive

• Sicilian • Downtown / Loop

Booked 30 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 Connie's Pizza in Bridgeport restaurant

3. Connie's Pizza in Bridgeport

4.6

Exceptional(756)

££££Price: Moderate

• Sicilian • 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 Paisans Pizza - South Loop restaurant

4. Paisans Pizza - South Loop

4.2

Awesome(53)

££££Price: Moderate

• Sicilian • South Loop

Booked 1 time today

Paisans Pizzeria was started by Luigi as a family business in Cicero, Illinois, back in 1985. Luigi started with one small oven, filling orders one at a time. Over time, Luigi’s success with the original Paisans allowed Pete, Luigi’s son, to take over and expand operations into Brookfield, Illinois; here the reputation of our award-winning, thin crust, Chicago-style pizza grew and grew! Were now serving thousands of satisfied customers every day in-house, by delivery and at special catered events.

A photo of Pizzeria Portofino restaurant

5. Pizzeria Portofino

4.8

Exceptional(1731)

££££Price: Expensive

• Sicilian • River North (Chicago)

Booked 204 times today

Pizzeria Portofino, nestled on the scenic Chicago riverfront in River North, is a haven for seafood aficionados seeking authentic flavors. Renowned for its exquisite seafood offerings, the restaurant skillfully captures the essence of the Italian Riviera. Diners rave about the "melt-in-your-mouth flavors" and "amazing food," ensuring every dish is a culinary delight. The coastal ambiance, paired with impeccable service, creates an inviting atmosphere that enhances the seafood experience. With a reputation for exceeding expectations, Pizzeria Portofino is a must-visit for those who appreciate quality and authenticity in seafood cuisine, making it a standout gem in Chicago's vibrant dining scene.

A photo of Quartino - Chicago restaurant

6. Quartino - Chicago

4.6

Exceptional(11108)

££££Price: Moderate

• Sicilian • River North (Chicago)

Booked 151 times today

Quartino Ristorante in Chicago's vibrant River North neighborhood offers an authentic slice of Italy with its exceptional Pizzeria cuisine. Known for its Neapolitan thin-crust pizzas, Quartino consistently delights diners with its "delicious food and service," as one regular praises. The pizzas are a standout, with rave reviews highlighting them as a "favorite place for pizza in Chicago." The lively atmosphere and attentive staff add to the warmth and charm of the dining experience. Perfectly capturing the essence of Italian dining, Quartino's pizzas are "a big hit," making it a must-visit for anyone seeking genuine Pizzeria flavors in the city.

7. Ummo

4.4

Awesome(553)

££££Price: Moderate

• Sicilian • River North (Chicago)

Booked 22 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 Olio e Più - Chicago restaurant

8. Olio e Più - Chicago

4.4

Awesome(1092)

££££Price: Expensive

• Sicilian • River North (Chicago)

Booked 65 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.

9. Osteria Via Stato

4.7

Exceptional(3496)

££££Price: Expensive

• Sicilian • River North (Chicago)

Booked 20 times today

Osteria Via Stato, a Lettuce Entertain You restaurant follows the Italian tradition of seasonally prepared dishes featuring local ingredients and artisanal producers paired with an all Italian wine list. Open for Lunch, Tuesday - Friday at noon - 2PM.Join us for Happy Hour everyday for 1/2 priced pizzas and glasses of wine, Sunday - Thursday at 5PM - 6PM, Friday - Saturday at 4:30PM - 5:30PM.

10. the Albert

4.3

Awesome(900)

££££Price: Expensive

• Sicilian • Gold Coast / Streeterville

Booked 5 times today

At the Albert, American cuisine reaches new heights with an extraordinary blend of quality, authenticity, and creativity. Situated in the vibrant Gold Coast/Streeterville area of Chicago, the Albert is celebrated for its "fantastic food and ambiance," offering diners an exceptional experience that tantalizes the senses. With a commitment to using high-quality, locally-sourced ingredients, including produce from its own rooftop garden, the Albert elevates traditional American dishes to a new level of freshness and flavor. Guests rave about the "excellent service" and the "gorgeous atmosphere," making every meal a memorable occasion. It's no surprise that diners are eager to return for more!

‘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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