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Best Fun Restaurants in Little Italy / University Village

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34 restaurants available nearby

A photo of Pizzeria Portofino restaurant
1. Pizzeria Portofino
4.7
Exceptional(1469)
Price: Expensive
• Italian • River North (Chicago)
Booked 213 times today
Pizzeria Portofino is a sun-drenched casual restaurant located directly on the Chicago riverfront offering hand-stretched pizzas, coastal wines, an expansive patio and breezy decor that will instantly transport you to the Italian Riviera.
A photo of Three Dots and a Dash restaurant
2. Three Dots and a Dash
4.7
Exceptional(1802)
Price: Expensive
• Cocktail Bar • River North (Chicago)
Booked 55 times today
With a secret alleyway entrance, Three Dots and a Dash is a speakeasy-style take on the traditional island bar—ready to transport you to the glamorous bygone eras of Trader Vic, Stephen Crane and Don the Beachcomber. Descend underground to discover a subterranean hideaway featuring a rum-soaked menu of more than two dozen classic, modern and original tropical cocktails and a selection of island fare. We are a 21+ venue.
A photo of Robert's Pizza and Dough Company restaurant
3. Robert's Pizza and Dough Company
4.8
Exceptional(2014)
Price: Expensive
• Pizzeria • Gold Coast / Streeterville
Booked 75 times today
Robert's Pizza and Dough Company serves it's award winning thin-crust artisanal pizzas with fresh and unique ingredients.
A photo of SUSHI-SAN - River North restaurant
4. SUSHI-SAN - River North
4.8
Exceptional(1275)
Price: Moderate
• Japanese • River North (Chicago)
Booked 121 times today
Sushi-San serves up the best sushi in Chicago made with the freshest ingredients they can find, all served with a side of old-school hip-hop and ice-cold beer. The bar is kept stocked with rare Japanese whisky, sake, wine and inventive cocktails. Join them for lunch and dinner.
A photo of Upstairs at The Gwen restaurant
5. Upstairs at The Gwen
4.2
Awesome(236)
Price: Expensive
• American • River North (Chicago)
Booked 26 times today
Experience the premier terrace in River North, located on the 5th floor of The Gwen, a one MICHELIN Key hotel, nestled along the iconic Magnificent Mile! Savor creative cocktails and indulge in delicious small and large plates crafted by Executive Chef Matt Jergens, all while enjoying the warm ambiance of our firepits and the stunning backdrop of towering skyscrapers. Our candlelit indoor lounge and bar offer the perfect setting to unwind, relax, and embrace the good life!Join us on the weekends for Chicago's liveliest, most unique tea service, Tipsy Tea! Featuring scrumptious savory and sweet bites, bottomless beverages, a DJ spinning, and a special themed menu every month, this is one pinkies-down tea service you will never forget!
A photo of Parlay River North restaurant
6. Parlay River North
4.4
Awesome(34)
Price: Moderate
• American • River North (Chicago)
Booked 14 times today
Parlay River North, located within the vibrant Joy District at 112 W Hubbard St, offers a high-energy sports bar experience perfect for both casual outings and lively nights out. This modern sports parlor on the first floor serves elevated bar fare alongside a curated selection of drinks in a dynamic and engaging atmosphere. Guests can enjoy American classics while watching the latest sports events on numerous big screens, ensuring they never miss a moment of the action. The stylish and comfortable setting, inspired by contemporary trends, provides a welcoming space for sports enthusiasts and casual visitors alike.Whether you're here for the game, a night out with friends, or a private event, Parlay River North promises a memorable experience with its vibrant ambiance and top-notch service. Come for the sports, stay for the food, drinks, and unbeatable energy.NO OUTSIDE LIQUOR,NO BIG BAGS, 1 BAG PER PERSON, NO RUBBER SOLES…Exceptions can be made on a case by case basis
A photo of Pilsen Yards restaurant
7. Pilsen Yards
4.7
Exceptional(1591)
Price: Moderate
• Mexican • Pilsen
Booked 23 times today
Pilsen Yards is a bar-centric and music-driven hangout in the heart of Pilsen with an open air vibe and one of the largest patios in the city.Exec. chef Juan Carlos Gutierrez's menu of latin-inspired street food, from tacos to ceviches, hummus to carne asada is plated up next to a mezcal, tequila, & whiskey charged bar program from bev director Lance Bowman, and it’s all on the cheap.
A photo of JoJo's ShakeBAR - River North restaurant
8. JoJo's ShakeBAR - River North
4.1
Excellent(2610)
Price: Moderate
• American • River North (Chicago)
Booked 152 times today
JoJo’s ShakeBAR is a next-generation restaurant and bar, and River North’s next go-to spot for hangouts, first dates, and family affairs. Its’ modern, yet familiar, diner experience is grounded in nostalgia and focuses on creative desserts and elevated diner favorites.Outdoor Patio Seating is available for reservations and walk-ins. In the case of inclement weather, our team will do our best to accommodate outdoor patio reservations inside, but indoor seating is not guaranteed. Reservations Are Highly Recommended & Walk Ins Are Available Based Upon Availability.
A photo of Parlor Pizza Bar - River North restaurant
9. Parlor Pizza Bar - River North
4.6
Exceptional(893)
Price: Moderate
• American • River North (Chicago)
Booked 52 times today
For more information please email info@parlorchicago.com . Entire party must be present to be seated.
A photo of Recess restaurant
10. Recess
4.5
Awesome(1463)
Price: Expensive
• American • West Loop
Booked 7 times today
Located in Chicago’s West Loop, Recess (838 W. Kinzie St.) offers a vibrant, playful, escape to the daily grind. Home of Chicago’s largest patio, Recess encourages guests to adult…like a kid, while serving up delicious American food and drink. The Recess menu taps into the cravings of everyday life, offering casually elevated dishes with playful Chicago swagger, while our beverage program takes a bright, ingredient-driven approach with cocktails both classic and original. In addition to the energetic adult playground vibes and menu offerings, Recess also offers a nostalgic array of indoor and outdoor activities including giant Jenga and Connect 4, all of your favorite board games.Recess is a 21+ establishment.

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