The Up Room
Thanks to a recent makeover, this towering Wicker North haunt atop The Robey’s iconic flatiron building sports an interior aesthetic just as sexy as its exterior panorama. Settle into the plush mid-century modern lounge seating and revel in the atmosphere as you dive into seasonal cocktails (don’t miss the Oaxacan on Broken Glass, a mix of mezcal, Ancho Reyes, lime, Angostura Bitters, and Hellfire Bitters) and killer charcuterie boards. This intimate and approachable space, set to a soothing soundtrack, makes for an ideal venue for romantic post-dinner nightcaps and first dates alike. A few floors down, Cabana Club’s rooftop oasis in the same building will open for the season on Cinco de Mayo until Labor Day. Located on the 6th floor, people know this comparatively pint-sized patio for its 180-degree vistas overlooking the L tracks, as well as its chic wading pool. Cabana Club 2023 sports a drink menu heavy on summer-inspired quaffs, like Spiked Sweet Tea, Pisco Punch, and a new frozen iteration of The Up Room’s Oaxacan on Broken Glass. Meanwhile a new food menu from chef Michael Eliott draws inspiration from Mexican and barbecue cuisines, resulting in equally summery flavors like Barbecued Pork Tacos and Chipotle Chicken Quesadillas.
How to book: Stop by for first come, first served seating.