ZipPicks Awards
Best Rooftop Restaurants in Loop
Master Critic Review
Boleo
8.3
A South American rooftop lounge with a retractable roof that leans festive—strong cocktails, ceviche-and-empanada energy, and a room that plays well for date nights and small groups. It’s best when you order in the pisco/ceviche lane early, then anchor the table with one bigger plate.
Must-Try Dishes:
Ceviche, Empanadas, Lomo Saltado
Scores:
Value: 7.3
Service: 7.9
Consistency: 8.2
Food Quality: 8.4
Atmosphere: 8.9
Cultural Relevance: 8.1
What makes it special: A retractable-roof rooftop that stays “party-ready” in any weather.
Who should go: Cocktail-first diners and date nights that want energy.
When to visit: Happy hour into early dinner for cleaner service flow.
What to order: Pisco cocktails, ceviche, empanadas or lomo saltado.
Insider tip: Reserve—walk-ins get squeezed hardest on prime weekends.
Logistics & Planning
Parking: Best move is nearby garages (street parking is scarce in the Loop). Expect paid garage parking within a few blocks; weekends/events can spike demand, so budget extra time.
Dress code: Smart casual leaning dressy—heels and elevated fits won’t feel out of place. Jeans are fine if styled up; avoid ultra-casual athleisure.
Noise level: Moderate-to-loud—high energy with music. Fine for conversation early; later nights get louder and more lounge-like.
Weekend wait: 45–90 min without a reservation (prime 7–10pm fills fastest).
Weekday lunch: Not a lunch-first spot—typically minimal waits earlier in the day, but happy hour can still run 15–30 min.
Dietary Options
Vegetarian options: Yes—shareable-friendly options like empanadas and vegetable-forward small plates work well; you can build a full meal with a couple of plates.
Vegan options: Limited—possible with careful ordering (often more snack/small-plate style than a full entrée lane). Ask what can be made plant-based.
Gluten-free options: Moderate—ceviche and certain shareables can fit, but cross-contact is possible in a rooftop lounge kitchen. Ask staff to guide you.
Best For
Better for: Retractable-roof rooftop energy that still works when the weather turns—plus a cocktail-forward menu that makes the night feel like a ‘scene’ rather than just dinner.
Consider Alternatives If: You want quiet conversation, a steakhouse-style formal meal, or guaranteed seating without planning—pick a calmer dining room or a reservation-required restaurant when timing matters.