Enable JavaScript to run this app.
Skip to main content
OpenTable logo
  1. Home
  2. United States
  3. Chicago / Illinois

Best Contemporary Italian Restaurants in Old Town

Price
Regions
Neighborhoods
Top Rated
Dining Options
Seating Options
Award-winning
Accessibility

7 restaurants available nearby

How are Featured results ranked

A photo of Fioretta restaurant
1. Fioretta
4.7
Exceptional(1076)
Price: Very Expensive
• Contemporary italian • West Loop
Booked 70 times today
Fioretta in Chicago's vibrant West Loop district is a cocktail bar that truly stands out with its "incredible drinks crafted to perfection." The bar experience is enhanced by the lively atmosphere, often featuring live music that adds to the allure of an unforgettable night out. Patrons rave about the attentive and friendly bartenders who ensure each cocktail is a masterpiece, making you feel like a "VIP in an establishment like this." Fioretta's cocktails are seamlessly integrated into the overall dining experience, providing an exquisite balance of flavors that mirror the restaurant's opulent and nostalgic ambiance. Perfect for those seeking a sophisticated yet inviting setting, Fioretta is a must-visit destination for cocktail enthusiasts.
A photo of Starbucks Reserve® Chicago Roastery restaurant
2. Starbucks Reserve® Chicago Roastery
4.8
Exceptional(56)
Price: Expensive
• Contemporary italian • River North (Chicago)
Booked 2 times today
The World's Largest Starbucks.A spectacular destination. Our passion for craft, innovation, and discovery comes to life in an ever-evolving menu of coffee, cocktails and food.An immersive and thoughtfully designed experience, this one-of-a-kind space will bring your event to life in a uniquely memorable way.
A photo of Wonderland at Tree House restaurant
3. Wonderland at Tree House
4.3
Awesome(304)
Price: Moderate
• Contemporary italian • River North (Chicago)
Booked 58 times today
✨ Fall down the rabbit hole into Wonderland—Chicago’s newest pop-up experience where curiosity leads to magic and every corner tells a story! 🌸💫 Think Mad Hatter tea parties, dreamy cocktails, oversized blooms, and photo ops straight out of your wildest imagination.From playful surprises to enchanting decor, Wonderland is the perfect escape for dreamers, romantics, and anyone craving a night unlike any other. Whether you're sipping a "Drink Me" potion or striking a pose with the Queen of Hearts, expect an unforgettable adventure full of charm and cheek.Bring your curiosity, your crew, and your best Wonderland look—it’s time to get wonderfully lost! 🐇
A photo of Pinstripes - Chicago restaurant
4. Pinstripes - Chicago
4.5
Awesome(577)
Price: Moderate
• Contemporary italian • Gold Coast / Streeterville
Booked 1 time today
Pinstripes: Where Sophisticated Fun Meets Exquisite Dining. With over 30,000 square feet of entertainment space, indulge in scratch-made Italian-American cuisine, handcrafted cocktails, and a robust wine list. Enjoy our weekday happy hour from 4-6pm, or don't miss our famous bottomless brunch buffet on weekends. Experience modern bowling and bocce with full-service dining and entertainment options. Perfect for corporate gatherings, celebrations, or family events, our versatile spaces accommodate parties of 20 to 1000 guests. Book your unforgettable experience today!
A photo of The Palm Chicago restaurant
5. The Palm Chicago
4.5
Awesome(2234)
Price: Very Expensive
• Contemporary italian • Downtown / Loop
Booked 12 times today
At The Palm Chicago, Seafood enthusiasts will delight in the authentic taste of the ocean with every dish. Nestled in the heart of the Downtown Loop, this renowned restaurant has been serving “fresh jumbo Nova Scotia Lobsters” and delectable seafood dishes since 1926. Guests rave about the “exceptional sea bass” and “crab cakes,” emphasizing the quality and freshness that set them apart. The Palm is celebrated for its “superior experience in all aspects,” from the exquisite flavors to the attentive service. Whether you're a local or visiting Chicago, The Palm promises an unforgettable seafood dining experience that feels like home.
A photo of Pizano's Pizza & Pasta - Madison restaurant
6. Pizano's Pizza & Pasta - Madison
4.6
Exceptional(363)
Price: Moderate
• Contemporary italian • Downtown / Loop
Booked 28 times today
Pizano's Pizza & Pasta - Madison is a true gem in the heart of Chicago, offering an authentic Pizzeria experience that has earned rave reviews from both locals and visitors. Known for its award-winning thin crust and bubbling deep dish pizzas, Pizano's delivers "the most delicious pizza in Chicago," as one delighted diner proclaimed. The restaurant, steeped in history with ties to the original creator of the deep dish, Rudy Malnati Sr., ensures every dish bursts with flavor thanks to high-quality ingredients and time-honored recipes. Diners love the "authentic dining experience" and impeccable service, often highlighted by the charming "Uncle Chach." For an unforgettable taste of Chicago, Pizano's is a must-visit.
A photo of Unico Restaurante restaurant
7. Unico Restaurante
4.9
Exceptional(13)
Price: Moderate
• Contemporary italian • Lower West Side
Booked 1 time today
Welcome to Unico Restaurante we look forward to serving you.
‘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
From verified diners like you

Explore OpenTable

Discover
OpenTable
  • About Us
  • Blog
  • Careers
  • Press
More
Our sites
Businesses
  • Restaurant Management Solutions
  • Restaurant Reservation Software
  • Restaurant Marketing Software
  • Restaurant Event Software
  • OpenTable For Restaurants
  • OpenTable For Restaurant Groups
  • Restaurant Resources
  • OpenTable Pricing & Plans
Join us on
  • Privacy Policy
  • Terms of Use
  • Cookies and Interest-Based Ads
  • Do Not Sell or Share My Personal Information
  • Cookie Preferences
Copyright © 2025 OpenTable, Inc. 1 Montgomery St Ste 500, San Francisco CA 94104 - All rights reserved.
OpenTable is part of Booking Holdings, the world leader in online travel and related services.
Booking Logo
Priceline Logo
KAYAK Logo
Agoda Logo
OpenTable Logo