August is upon us in Chicago but summer’s just starting to heat up. And what better way to soak up the day’s rays and warm, balmy nights than on the city’s most coveted rooftops? From our very own eleventh-floor deck at One Two Pru to the rooftop restaurant and bar at Cindy’s (just steps away from our landmark address), there’s no shortage of sweeping city views and stellar cocktails to drink up this month in Chicago. Below, read up on our team’s favorite rooftops to savor the last of summertime in the city. 

Rooftop Deck at One Two Pru

Set high above Millennium Park with incredible lakefront and skyline views, the 7,000-square-foot rooftop deck at One Two Pru offers the most idyllic set-up for tenants to kick back with colleagues or indulge in some me-time in an exclusive, sky-high environment. Featuring a grassy lawn, multiple lounge spaces and amphitheater seating, the eleventh-floor rooftop deck is surely our go-to rooftop in the city…particularly after-hours when Chicago is set aglow and we have a beverage in hand.


Down the street from One Two Pru at the Chicago Athletic Association Hotel lies the ultimate spot for cocktail-lovers: Cindy’s. Set to our same views, just from a different angle, Cindy’s rooftop restaurant and bar is helmed by Executive Chef Christian who dishes out seasonal, family-style comfort food, bio-dynamic wines and award-winning cocktails. For summer? Be sure to sip on a Stoop Hangs that’s made with pau maui vodka, rhine hall pineapple brandy, orgeat, pineapple cordial, lemon and tarragon.