Hotel Rooftop Bar · River North
Upstairs at The Gwen
67
now
Upstairs at The Gwen is a polished hotel rooftop retreat above Rush Street, pairing skyline views with cocktail-bar and Mediterranean/American dining service. It is a strong replacement candidate because the official source exposes current structured hours and clear rooftop positioning.
Go here if
- You want cocktails.
- Rush Street hotel rooftop with broad daypart utility and source-backed hours.
- You need some weather backup instead of a fully exposed deck.
Skip if
- You want a budget-first night.
Booking reality
Use the OpenTable flow linked directly from the official Upstairs at The Gwen page.
Source confidence
official
Official source exists, community signal still worth checking.
Hours confidence
source-backed
Official Upstairs page visible service hours list breakfast/brunch Monday-Friday 7 AM-11 AM and Saturday-Sunday 7 AM-2 PM, lunch Monday-Friday 11 AM-4 PM, and dinner Monday-Thursday 4 PM-9:30 PM, Friday 4 PM-10:30 PM, Saturday 2 PM-10:30 PM, Sunday 2 PM-9:30 PM; JSON-LD/Rooftop Guide still summarize broader public hours as Sunday-Thursday 7 AM-11 PM and Friday-Saturday 7 AM-1 AM.
Weather caveat
source-backed
Best for mild rooftop weather, with some source-backed fallback: official copy supports a rooftop terrace plus cozy indoor lounge, and directory cross-checks support fire pits/cold-weather activation. Still not a fully covered/retractable-roof venue.
Score card
Why now
Why now: Good brunch timing and good afternoon fit.
84°F · 15 mph wind · 5% rain risk
67
now
Sunset
7/10
How strong the views land at golden hour.
Shade
5/10
Useful when the sun starts acting rude.
Resilience
6/10
Cover, heaters, and weather tolerance.
Late night
5/10
Whether this still works after dinner.
Why it belongs
Rush Street hotel rooftop with broad daypart utility and source-backed hours.
Best for mild rooftop weather, with some source-backed fallback: official copy supports a rooftop terrace plus cozy indoor lounge, and directory cross-checks support fire pits/cold-weather activation. Still not a fully covered/retractable-roof venue.
Best for
- cocktails
- hotel rooftop drinks
- out-of-town guests
- sunset views
Vibe
Ratings and reviews
Nearby alternatives
Similar choices if this one misses
Hotel Rooftop Restaurant
Cindy's Rooftop
Chicago Athletic Association rooftop with Millennium Park, Lake Michigan, and skyline views.
Hotel Rooftop Bar
LH Rooftop
Tri-level LondonHouse rooftop with iconic river, skyline, and Lake Michigan views.
Rooftop Restaurant
Offshore Rooftop
Massive multi-season Navy Pier rooftop with lakefront views and full-service bar-and-kitchen scale.