Best Italian Restaurants in South Side

Price

€€
€€€
€€€€

Regions

ChicagoNear WestSouth Suburbs

Areas

Bedford ParkBelmont CraginBerwynBridgeportBucktown / Wicker ParkDowntown / Loop

Top Rated

CharmingFancyGood for business mealsGood for groupsGood for special occasionsGreat for brunch

Dining Options

All dining options

Delivery only

Takeaway only

Seating options

BarCounterStandardHigh TopOutdoor

Award-winning

James Beard AwardMICHELIN

Accessibility

Wheelchair access

128 restaurants available nearby

How are Featured results ranked

The default order for search results reflects a number of factors, including table availability, restaurant location, search criteria, and restaurant reviews and ratings. In addition, payment made by a restaurant to OpenTable is also a factor for the relative ordering of restaurants.

1. Alla Vita

4.8

Exceptional(2530)

€€€€Price: Expensive

• Italian • West Loop

Booked 162 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.

2. Il Culaccino

4.4

Awesome(1117)

€€€€Price: Moderate

• Italian • South Loop

Booked 25 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 Franco's Ristorante restaurant

3. Franco's Ristorante

4.9

Exceptional(681)

€€€€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 Connie's Pizza in Bridgeport restaurant

4. Connie's Pizza in Bridgeport

4.7

Exceptional(766)

€€€€Price: Moderate

• Italian • South Loop

Booked 10 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.

5. Acanto

4.8

Exceptional(4029)

€€€€Price: Expensive

• Italian • Downtown / Loop

Booked 63 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 Dolce Arte - The Art of Food restaurant

6. Dolce Arte - The Art of Food

4.6

Exceptional(25)

€€€€Price: Moderate

• Italian • Bridgeport

Booked 4 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 Lou Malnati's - South Loop restaurant

7. Lou Malnati's - South Loop

4.6

Exceptional(155)

€€€€Price: Moderate

• Italian • South Loop

Booked 35 times today

Lou Malnati's in South Loop is a quintessential Chicago eatery renowned for its authentic American cuisine, particularly its "legendary" deep dish pizza. Nestled on South State Street, this iconic spot has been perfecting its craft for over 50 years, promising an "unforgettable" experience for anyone craving genuine Chicago flavor. Diners rave about the "buttery crust" and "scrumptious" pizzas, making it a must-visit for both locals and tourists alike. The cozy atmosphere and "flawless" service ensure that every visit is memorable. Whether you're fresh from sightseeing or a sporting event, Lou Malnati's offers a true taste of classic American dining.

8. The Florentine

4.5

Awesome(1320)

€€€€Price: Expensive

• Italian • Downtown / Loop

Booked 31 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.

9. Sofi Restaurant

4.7

Exceptional(1708)

€€€€Price: Expensive

• Italian • South Loop

Booked 14 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.

10. Tuscany on Taylor

4.8

Exceptional(2259)

€€€€Price: Moderate

• Italian • Little Italy / University Village

Booked 24 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.

See what locals rave about

From verified diners like you

L
Lynne
Chicago / Illinois •16 reviews
5.0
Dined 1 day ago
First time at Acanto… what a treat! Hannah was a fantastic server with a quick wit. Food was excellent. Water was constantly refilled and table was bused instantly. Manager served our wine and gave us his card for future use. Oh and… the first restaurant to actually respond to my text requesting a table with extra leg room(long story). Acanto checked all the boxes and we look forward to returning to this gem of a restaurant!
More info
AcantoPrice: Expensive• Italian• Downtown / Loop
•
4.8
V
VickiVIP
Chicago / Illinois •58 reviews
5.0
Dined 2 days ago
The food is very good. It's one of the best restaurants in the West Loop. But this place goes for noisy. If that's your thing, good for you. Wish there were a way to kill the not-so-great soundtrack and decrease the shouting that customers have to do to communicate (which also increases the noise level).
More info
Alla VitaPrice: Expensive• Contemporary Italian• West Loop
•
4.8
R
Robert
Chicago / Illinois •6 reviews
5.0
Dined 5 days ago
Great pizza as always. We had the Sicilian pan tonight with sausage mushroom. Service had a couple hiccups but overall great as always.
More info
Connie's Pizza in BridgeportPrice: Moderate• Italian• South Loop
•
4.7
W
WendyVIP
Washington, D.C. Area •10 reviews
4.0
Dined 5 days ago
Good option near McCormick Place if you’re at a conference. Otherwise I wouldn’t go out of my way.
More info
Il CulaccinoPrice: Moderate• Italian• South Loop
•
4.4
T
TimothyVIP
Chicago / Illinois •2 reviews
4.0
Dined on 20 May 2025
Great food, great atmosphere, great service!Loved it!
More info
Franco's RistorantePrice: Moderate• Italian• Bridgeport
•
4.9

Explore OpenTable

Area
Cuisine nearby
Italian cuisine

South Side

Italian

River West
Blue Island
St. Charles
Skokie
Elk Grove Village
Lake Zurich
Wilmette
Arlington Heights
Orland Park
Northbrook
Franklin Park
West Dundee
Old Town
Downtown / Loop
Munster, IN
Addison
Darien
Brookfield
Aurora
Burr Ridge