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 Canal Street Eatery and Market?

Ask for fries right away—then add food as you go.

When should I visit Canal Street Eatery and Market?

Late lunch for the calmest ordering flow.

Who should go to Canal Street Eatery and Market?

Loop lunchers who want a sure-thing side.

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.

Best Date Night Italian Restaurants in Loop (60606)

3 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 Canal Street Eatery and Market

8.1

$$ West Loop Gate

Vibes: Business Lunch Power Players Quick Bites Champions Group Dining Gatherings Hidden Gems Heaven

An Italian-leaning eatery/market in the BMO Tower corridor where fries show up as the reliable side move for sandwiches and burgers—simple, salty, and built for dipping into house aioli. It works best as a flexible lunch basecamp: grab a sandwich, keep fries hot, and add a slice or small plate if you’re lingering.

Must-Try Dishes: Fries, Canal Burger, Rigatoni

What makes it special: Office-corridor eatery where fries and sandwiches stay dependable.

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Worthy Picks

#3 Pazzo's

7.9

$$ The Loop

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

A dramatic atrium dining room that feels like a built-in occasion, even when the order stays classic. Treat it like a comfort-forward Italian night: one pizza, one pasta, and a shared starter, letting the room do most of the date-night work.

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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