There’s something magical about watching the sun dip below a city skyline, especially when you’re doing it from a rooftop oasis above the buzzing streets of Chicago. At The Robey, nestled in the heart of Wicker Park, that magic becomes your everyday view. With its art deco charm, sweeping rooftop panoramas, and a vibe that mixes vintage cool with contemporary luxury, The Robey isn’t just a place to stay—it’s where you come alive above the city. Whether you’re sipping a craft cocktail poolside, soaking up golden-hour hues, or simply lounging on a rooftop daybed, The Robey transforms your Chicago stay into something cinematic.
A Rooftop That Captures the City’s Soul
The real star of The Robey is its rooftop lounge, aptly named Up Room. Perched on the 13th floor, this sleek yet intimate space offers one of the best views of the Chicago skyline. By day, you can settle into a modernist couch with a cold drink in hand, and by night, you’re enveloped by a moody ambiance with dim lights, deep conversations, and the city glittering in the distance. It’s a rare place where you can feel both completely connected to the city and totally removed from the chaos below.
Up Room doesn’t just offer a view—it creates a mood. The decor blends minimalist design with warm textures, inviting guests to unwind in style. Whether you’re starting your night or winding it down, this rooftop is the kind of place you linger a little longer than planned.
A Rooftop Pool That’s a Hidden Gem
Not many hotels in Chicago can brag about a rooftop pool, and even fewer can match the charm of The Robey’s Cabana Club. Located one floor below the Up Room, this space features a plunge pool with unobstructed skyline views. It’s not oversized, and that’s exactly the point. Instead, the intimate scale gives it a boutique-like atmosphere—exclusive yet unpretentious.
During summer months, guests gather here to sip frozen cocktails, stretch out on sun loungers, and take in the sounds of the neighborhood’s indie energy drifting up from the streets below. With palm-style umbrellas, stylish deck chairs, and curated playlists, the Cabana Club gives serious rooftop beach club vibes—without leaving the city.
Timeless Design in Every Detail
Staying at The Robey feels like stepping into a Wes Anderson film—if Wes Anderson did Chicago. The building itself is a restored 1929 art deco masterpiece, with rooms that honor their historic roots while embracing modern comforts. Think crisp white bedding, warm wooden floors, industrial-style windows, and curated artwork that hints at Chicago’s layered history.
From the café downstairs (serving up fresh pastries and cold brews) to the friendly staff who remember your name, every corner of this hotel feels considered. It’s not over-the-top luxury; it’s quiet, confident, and effortlessly cool.
Q&A: Planning Your Rooftop Escape
Q: What time is best to visit the rooftop at The Robey?
A: Sunset is prime time. Arrive an hour before dusk to secure a cozy seat and watch the golden light dance off the cityscape.
Q: Is the rooftop open year-round?
A: The Up Room is open all year, with a cozy indoor bar for colder months. The pool at Cabana Club, however, is seasonal—typically open from May through early September.
Q: Do you have to be a hotel guest to access the rooftop?
A: The Up Room is open to the public, but the Cabana Club and rooftop pool are for hotel guests only—one more reason to book a room and stay the night.
Other Hotels with Elevated Rooftop Experiences
1. LondonHouse Chicago – Right on the river, this hotel’s rooftop boasts a sweeping tri-level terrace and is a favorite for brunch with a view.
2. The Gwen – Tucked into the Magnificent Mile, its rooftop terrace offers art-inspired cocktails and creative city vibes.
3. Viceroy Chicago – Stylish and upscale, the rooftop bar here is perfect for a polished night out with panoramic views of the Gold Coast.
The Final Word
To lounge in rooftop paradise at The Robey is to experience a side of Chicago that’s refined, relaxed, and just a little bit rebellious. You’re not in the tourist zone—you’re in the neighborhood where the city breathes culture, art, and style. Whether you’re sipping rosé beside the pool, mingling over cocktails in the Up Room, or simply gazing out from your vintage-inspired room, The Robey offers a rooftop escape that’s far from ordinary. It’s elevated—not just in altitude, but in experience.