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Upstairs at The Gwen
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Master Critic Review
Upstairs at The Gwen
8.3
Upstairs at The Gwen turns the hotel’s fifth-floor terrace into an Art Deco-inspired rooftop with fire pits, city views, and a menu of cocktails and shareable New American plates. It balances hotel polish with a relaxed, social feel that works for dates, small groups, and seasonal events like Tipsy Tea.
Must-Try Dishes:
Curried Carrot Deviled Eggs, Spanakopita with Honey, Apricot-Cranberry Scones
Scores:
Value: 7
Service: 8.3
Consistency: 8.2
Food Quality: 8.2
Atmosphere: 9
Cultural Relevance: 8.1
What makes it special: Art Deco-inspired rooftop terrace with cocktails, snacks, and fire pits.
Who should go: Groups or couples wanting polished rooftop vibes above Michigan Avenue.
When to visit: Thursday evenings for Terrace & Tunes and sunset light.
What to order: Curried Carrot Deviled Eggs, Spanakopita with Honey, Apricot-Cranberry Scones.
Insider tip: Reserve early; terrace tables go first on mild nights.
Logistics & Planning
Parking: Hotel valet available at The Gwen (typically premium pricing); nearby garages along Rush & Michigan; limited street parking in the area.
Dress code: Smart casual — jeans are fine but most guests lean dressy with polished tops, jackets, or cocktail-casual attire.
Noise level: Moderate — social rooftop energy with music but you can generally hold a conversation at standard tables.
Weekend wait: 30–60 minutes without a reservation during warm, clear evenings.
Weekday lunch: Usually no wait when daytime service is offered; many visits are evenings/seasonal only.
Dietary Options
Vegetarian options: Yes — several small plates and snacks can be made or ordered vegetarian.
Vegan options: Limited — usually 1–2 items or modifiable plates; best to ask your server.
Gluten-free options: Several naturally gluten-free options and modifications available, but no dedicated prep area.
Good to Know
Is this good for a first date? Yes — the terrace lighting, city views, and fire pits create an intimate but relaxed atmosphere that works well for conversation without feeling overly formal.
Can I get a table without a reservation? Sometimes — walk-ins are possible earlier in the evening or on cooler nights, but prime weather and event nights fill quickly; arrive early or join the wait with the host.
Is it kid-friendly? Lightly — older kids and teens are fine during earlier hours, but the vibe skews adult-social and is better suited to dates and small groups than families with young children.
Best For
Better for: Art Deco ambiance, relaxed-luxury rooftop seating, and polished hotel service without the party-hard vibe of louder rooftops.
Skip if: You want a full dinner-centric menu, late-night party energy, or budget-friendly pricing — consider a more casual rooftop or lounge instead.