Upstairs at The Gwen

Skyline Sips and Elevated Bites at The Gwen

Modern and stylish, Upstairs at The Gwen is a rooftop restaurant and lounge perched atop The Gwen Hotel in downtown Chicago. Just steps from Michigan Avenue and a short walk to major concert venues, this chic urban escape blends Art Deco elegance with a trendy rooftop vibe. Offering a creative take on American cuisine, curated cocktails, and stunning skyline views, it’s an ideal spot for both relaxed afternoons and lively pre-show evenings.

Why Concert-goers love it

Location, location, location—Upstairs at The Gwen is perfectly situated for concert-goers heading to venues like the Chicago Theatre or House of Blues. The rooftop setting offers a lively yet not overwhelming atmosphere, making it a great place to grab a drink and a bite before or after a show. Service is typically attentive and fast, which means you can enjoy your meal without stressing about missing the opening act. In the warmer months, the open-air terrace creates a festive ambiance that pairs well with a night of live music.

Who this Restaurant is great for

• Groups of friends looking to kick off the night with craft cocktails and shareable plates
• Solo travelers wanting a scenic spot to relax before a show
• Couples planning a romantic weekend with rooftop views and downtown energy
• Fans seeking a trendy, social space to fuel up before the concert
• Budget-conscious music lovers who still want a taste of luxury (especially during happy hour)

What People Say

Reviewers on TripAdvisor and OpenTable consistently praise the ambiance, calling it “stylish,” “elegant,” and “perfect for a night out.” The rooftop setting is a huge hit, especially during sunset hours. Guests love the inventive cocktails and small plates, with favorites like truffle fries and sliders. Many note the friendly staff and great music, creating a vibe that feels festive without being overpowering. The location is repeatedly highlighted as a major plus for those attending downtown events.

Areas for Improvement

Some guests mention that the rooftop can get a bit crowded during peak hours, and seating may be limited without a reservation. Prices lean toward the higher end, which may be a consideration for those looking to keep things budget-friendly. Also, while the rooftop is open seasonally, indoor options are available year-round—but may lack the same wow factor as the terrace.

The Bottom Line

Upstairs at The Gwen offers concert-goers a stylish, convenient, and scenic spot to dine and unwind before the show starts.

Heading to ? Here's Why This Restaurant Fits the Bill

Perched atop The Gwen Hotel, Upstairs at The Gwen offers a chic rooftop escape with sweeping skyline views and a menu full of inventive American bites and cocktails. Conveniently close to House of Blues Chicago, this stylish spot is perfect for concert-goers looking to elevate their night with a touch of glamour. Whether you're sipping a craft cocktail on the open-air terrace or sharing small plates with friends, the vibrant yet relaxed atmosphere sets the perfect tone for an unforgettable evening downtown.