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Upstairs at The Gwen
Master Critic Reviews (2 Lists)
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.
Upstairs at The Gwen
8.0
Perched above Rush Street, Upstairs at The Gwen is a rooftop lounge where skyline views, cocktails, and happy hour bites—including sauced wings—drive the experience more than volume eating. It’s the move when you want wings and drinks wrapped in fire pits, city views, and hotel-bar polish.
Must-Try Dishes:
Happy Hour Chicken Wings, Lux Chicago Dog, Truffle Fries
Scores:
Value: 6.8
Service: 8.4
Consistency: 7.9
Food Quality: 7.8
Atmosphere: 9.2
Cultural Relevance: 8.2
What makes it special: Rooftop happy hour where wings, cocktails, and skyline views land on the same table.
Who should go: Groups prioritizing views and drinks but still craving wings.
When to visit: Weekday happy hour for daylight-to-dusk views and space.
What to order: Happy hour wings, truffle fries, one of the seasonal cocktails.
Insider tip: In cooler months, aim for a fire pit table so wings and drinks don’t cool too fast.
Logistics & Planning
Parking: Hotel valet in the Gwen/AC Hotel garage is the most reliable option; street parking nearby is limited and fills quickly during evenings and weekends.
Dress code: Smart casual leaning dressy — elevated rooftop vibe; jeans are fine if styled, athleisure and beachwear may feel out of place.
Noise level: Moderate to lively — conversation is doable at lounge seating, but bar and fire-pit areas get louder as the night progresses.
Weekend wait: Expect a wait or slower seating without a reservation, especially during prime sunset hours.
Weekday lunch: Typically no wait — service is lighter outside of peak rooftop and happy hour windows.
Dietary Options
Vegetarian options: Yes — shareable snacks, salads, and sides usually offer a few vegetarian-friendly options.
Vegan options: Limited — some sides or modified plates may work, but menus skew toward bar snacks and proteins.
Gluten-free options: Moderate — several cocktails and a handful of dishes can be prepared gluten-free on request; confirm with staff.
Good to Know
Is this good for a first date? Yes — the rooftop setting, skyline views, and fire-pit seating create a relaxed, scenic atmosphere that works well for a conversational first or second date, especially around sunset.
Can I get a table without a reservation? Often yes during weekdays and earlier hours, but on warm evenings and weekends walk-ins may be waitlisted; arriving early or aiming for bar or lounge seating improves your chances.
Is it kid-friendly? Better suited to adults — it functions primarily as a cocktail-forward rooftop lounge; older teens may be fine during daytime or early evening, but it’s not designed for young children.
Best For
Better for: Scenic happy hour wings, polished hotel-rooftop ambiance, and drinks with skyline views rather than large-format dining.
Skip if: You’re seeking big portions, casual sports-bar pricing, or a wings-first destination — choose a dedicated pub or wing spot instead.