What is the best Italian restaurant in Loop?

Gibsons Italia is our top pick for Italian restaurants in Loop, scoring 8.7/10. Italian steakhouse where serious pastas meet river and skyline views.

Any insider tips for Gibsons Italia?

Request terrace or window seating when reserving for full river impact.

What should I order at Gibsons Italia?

Spicy Rigatoni, a Prime steak cut, Roasted Mediterranean Branzino.

When should I visit Gibsons Italia?

Golden-hour dinners for views or prime business-lunch windows.

Who should go to Gibsons Italia?

Clients and couples wanting upscale Italian steakhouse polish.

Any insider tips for Pazzo's?

Ask about event-style menus if you’re dining with a larger group.

When should I visit Pazzo's?

Weekday lunch or evening events when the atrium feels lively.

Who should go to Pazzo's?

Teams, families and couples planning downtown Italian occasions.

Any insider tips for Leona's Pizzeria & Restaurant?

They were among the first to deliver pizza in Chicago—order delivery for the authentic Leona's experience

What should I order at Leona's Pizzeria & Restaurant?

Thin crust sausage (their signature), Detroit style for something different

When should I visit Leona's Pizzeria & Restaurant?

Weekday lunch for quick service; dinner for full experience

Who should go to Leona's Pizzeria & Restaurant?

Those wanting old-school Chicago pizza heritage with modern comfort

Any insider tips for Arturo Express?

Use combo deals to sample both pizza and pasta without overspending.

When should I visit Arturo Express?

Weekday lunch before the peak noon-to-one rush.

Who should go to Arturo Express?

Commuters and office workers wanting hearty, inexpensive Italian lunches.

Best Family Friendly Italian Restaurants in Loop (60606)

Q: What should I order at Pazzo's?

Chicken Vesuvio, Chicken Alonso, Rigatoni Bolognese.

4 hand-picked restaurants, critic-reviewed and ranked

Last Updated: January 2026

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Our Top Pick

Gibsons Italia

Italian steakhouse where serious pastas meet river and skyline views.

Notable Picks

#1 Gibsons Italia

8.7

$$$ Fulton River District

Vibes: Date Night Magic Luxury Dining Elite Business Lunch Power Players Trendy Table Hotspots

Gibsons Italia is a riverfront Italian steakhouse pairing gold-extruded pastas, Prime beef and seafood with skyline views from multi-level dining rooms. Downtown diners use it for client dinners, occasion meals and polished date nights where service and execution are tightly controlled.

Must-Try Dishes: Spicy Rigatoni, Cacio e Pepe, Roasted Mediterranean Branzino

What makes it special: Italian steakhouse where serious pastas meet river and skyline views.

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#2 Pazzo's

8.3

$$ The Loop

Vibes: Group Dining Gatherings Birthday & Celebration Central Business Lunch Power Players Comfort Food Classics

Pazzo’s @ 311 is a glass-roofed Italian restaurant and event space where handmade pastas, chicken Vesuvio and risotto come out under a soaring atrium. Office workers and wedding parties alike use it when they want classic Italian plates in a dramatic downtown room.

Must-Try Dishes: Chicken Vesuvio, Chicken Alonso, Rigatoni Bolognese

What makes it special: Atrium Italian dining that also functions as a full-scale event venue.

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#3 Leona's Pizzeria & Restaurant

8.0

$$ The Loop

Vibes: Family Friendly Favorites Comfort Food Classics Business Lunch Power Players Group Dining Gatherings

A 75-year Chicago institution since 1950, Leona's pioneered pizza delivery in the city and continues serving fresh, locally-sourced thin crust and Detroit-style pies. The modern Loop location offers full-service dining with a surprisingly diverse menu beyond pizza.

Must-Try Dishes: 16-Inch Thin Crust Sausage Pizza, Detroit Style Pizza, Italian Beef Sandwich

What makes it special: Chicago's pizza delivery pioneer since 1950, still family-owned after 75 years

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Worthy Picks

#4 Arturo Express

7.8

$ West Loop Gate

Vibes: Cheap Eats Budget Brilliance Quick Bites Champions Business Lunch Power Players Solo Dining Sanctuaries

Arturo Express is a daytime Italian cafe near Union Station known for Italian beef, hand-tossed pizzas, pastas and value-priced lunch combos. Commuters and office regulars rely on it for hearty, old-school Chicago Italian plates that move quickly without feeling like pure fast food.

Must-Try Dishes: Italian Beef, Arturo Signature Salad, Salad & 1/2 Pizza Combo

What makes it special: Union Station-adjacent Italian counter doing beef, pizza and pasta combos.

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