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Homestead on the Roof
ZipPicks Awards
Best Rooftop Restaurants in Wicker Park & West Town
Best Outdoor Dining Restaurants in Wicker Park & West Town
Best Tasting Menus in Wicker Park & West Town
Master Critic Review
Homestead on the Roof
8.4
Homestead on the Roof is a garden-topped restaurant above Roots Handmade Pizza, pairing a seasonal, globally influenced menu with an intimate rooftop setting. Diners come for pork belly, seafood, and tacos built around produce and herbs grown in the rooftop garden. It leans more like a date-night or small-group dinner spot than a casual drinks-only patio.
Must-Try Dishes:
Pork Belly, Scallop, Duck Rice
Scores:
Value: 7
Service: 7.4
Consistency: 8.1
Food Quality: 8.7
Atmosphere: 9.1
Cultural Relevance: 7.9
What makes it special: A tucked-away rooftop garden restaurant focused on seasonal, chef-driven plates.
Who should go: Couples and small groups craving cozy, upscale rooftop dinners.
When to visit: Warm evenings at golden hour for garden views and lighting.
What to order: Pork Belly, Scallop, Duck Rice.
Insider tip: Book earlier in the season; menus and availability change frequently.
Logistics & Planning
Parking: Street parking in West Town is available but can be competitive during dinner hours; allow extra time or consider rideshare.
Dress code: Smart casual — elevated but relaxed. Jeans are fine if styled nicely.
Noise level: Moderate — you can comfortably hold a conversation, though it gets livelier during peak dinner service.
Weekend wait: Reservations are strongly recommended; walk-ins may face long waits or limited availability.
Weekday lunch: Typically not applicable — service is primarily dinner-focused.
Dietary Options
Vegetarian options: Yes — seasonal vegetable-driven dishes are usually available.
Vegan options: Limited — menus change, but vegan items may be available with modifications.
Gluten-free options: Yes — several dishes can be prepared gluten-free; alert your server.
Good to Know
Is this good for a first date? Yes — the intimate rooftop garden, warm lighting, and seasonal menu make it an ideal romantic setting without feeling overly formal.
Can I get a table without a reservation? Sometimes, but it’s risky — the rooftop space is small and books up early, especially in warm weather. Walk-ins are best attempted early evening or on weekdays.
Is it kid-friendly? It’s technically allowed, but the atmosphere leans adult and date-night oriented. Older kids or teens may be fine; younger children may feel out of place.
Best For
Better for: Cozy, garden-style rooftop dining with chef-driven food in a more intimate, hidden-away setting than larger, party-driven rooftops.
Skip if: You’re looking for a loud rooftop bar scene, late-night energy, or a drop-in patio focused mainly on drinks rather than dinner.