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Best Italian Restaurants in South Side

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123 restaurants available nearby

A photo of Alla Vita restaurant
1. Alla Vita
4.8
Exceptional(2303)
Price: Expensive
• Italian • West Loop
Booked 78 times today
Alla Vita, nestled in Chicago's vibrant West Loop, is a beacon of contemporary Italian cuisine that delights with its casual, family-style dining. Celebrating life's triumphs, Alla Vita offers a menu bursting with authenticity and flavor. Executive Chef Lee Wolen's passion is evident in every dish, from the heavenly Whipped Ricotta with orange blossom honey to the exquisite burrata with hazelnuts. Patrons rave about the unforgettable "burrata app with toasted bread," and the "rigatoni alla vodka," describing them as "mouth-watering" and "incredible." The ambiance, described as "vibrant and beautiful," complements the culinary experience, making Alla Vita a must-visit for anyone seeking the finest in contemporary Italian fare in Chicago.
A photo of Franco's Ristorante restaurant
2. Franco's Ristorante
4.8
Exceptional(653)
Price: Moderate
• Italian • Bridgeport
Booked 3 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 Dolce Arte - The Art of Food restaurant
3. Dolce Arte - The Art of Food
4.7
Exceptional(13)
Price: Moderate
• Italian • Bridgeport
Booked 1 time today
Dolce Arte - The Art of Food in Bridgeport, Chicago, is a beacon of café culture, offering a delightful experience with its authentic Italian pastries and world-renowned LavAzza coffee. Patrons rave about the "amazing food" and the "excellent coffee," which stand as testaments to the café's commitment to quality and authenticity. One reviewer exclaimed, "Latte was amazing and the pastries were phenomenal!!!" The café's ambiance is equally praised, with its spacious, sunny setting that invites guests to relax and enjoy their visit. Whether it's grabbing a quick coffee or indulging in a leisurely brunch, Dolce Arte provides a perfect blend of superb cuisine, welcoming service, and a vibrant atmosphere, making it a must-visit destination in Bridgeport.
A photo of Acanto restaurant
4. Acanto
4.8
Exceptional(3852)
Price: Expensive
• Italian • Downtown / Loop
Booked 23 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.
A photo of Il Culaccino restaurant
5. Il Culaccino
4.1
Excellent(1089)
Price: Moderate
• Italian • South Loop
Booked 3 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 Connie's Pizza in Bridgeport restaurant
6. Connie's Pizza in Bridgeport
4.7
Exceptional(738)
Price: Moderate
• Italian • South Loop
Booked 15 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 Miss Ricky's Trattoria restaurant
7. Miss Ricky's Trattoria
4.6
Exceptional(808)
Price: Moderate
• Italian • Downtown / Loop
Booked 21 times today
Miss Ricky's Trattoria in Downtown Chicago stands out as a beacon of authentic Pizzeria cuisine. Nestled in a historic building on N. Wabash, this vibrant eatery delights with its fresh, from-scratch Italian dishes crafted by Executive Chef Mike Alaridi. Diners consistently rave about the "top-notch" Italian sausage pizza and the "incredible" prosciutto and mushroom pizza, highlighting the quality and authenticity that Miss Ricky's brings to the table. One reviewer exclaimed, "The food was absolutely delicious! We had the lasagna, seafood pasta, and prosciutto and mushroom pizza and every dish was incredible." Whether you're seeking a casual brunch or a lively dinner, Miss Ricky's Trattoria promises an exceptional dining experience with fantastic service in the heart of Chicago.
A photo of The Florentine restaurant
8. The Florentine
4.4
Awesome(1304)
Price: Expensive
• Italian • 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 Viaggio Ristorante and Lounge restaurant
9. Viaggio Ristorante and Lounge
4.9
Exceptional(2550)
Price: Moderate
• Italian • West Loop
Booked 14 times today
*PLEASE CALL TO SEE OTHER AVAILABLE RESERVATION TIMES*An authentic Italian dining experience in the heart of Chicago's lively West Loop neighborhoodWe offer an elegant and charming dining experience that keeps guests coming back again and again. Our large menu of regional Italian pastas, meats and fishes is rounded out by a selection of salads, soups, and decadent desserts. Popular staples like Rigatoni with Braised Pork Gravy and Eggplant Parmesan are served alongside Executive Chef Nicolas Biscaglio’s signature interpretations of classic Italian dishes. We use only the highest quality ingredients to ensure a deliciously memorable experience!​As a hospitality-driven establishment, it’s our goal to make every guest that walks through the door feel like family. At Viaggio, we invite you to sit back, relax and enjoy!
A photo of Sofi Restaurant restaurant
10. Sofi Restaurant
4.8
Exceptional(1670)
Price: Expensive
• Italian • South Loop
Booked 7 times today
Sofi Restaurant in South Loop, Chicago, is a culinary beacon for seafood lovers, renowned for its exceptional Italian seafood dishes. Chef Maurizio Michi brings his Milanese expertise to the table, crafting standout seafood creations like the perfectly grilled Sea Bass Branzino and the rich, flavorful Fish Stew Viareggina. Patrons rave about the authenticity and freshness of the seafood, with one diner enthusing, "The seafood and pasta dish were very happy and delicious." Sofi's commitment to quality is evident in every dish, making it a must-visit for those seeking the finest seafood in an inviting, authentic Italian setting.
‘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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