If you’re into city views, outdoor/indoor rooftop lounge with heated lamps to keep you at the perfect temperature, then Cindy’s Rooftop Restaurant and Bar is calling your name. Cindy’s rooftop restaurant is located on Michigan Ave across from Millennium Park. It has crafted cocktails (and mocktails) and unparalleled views of the city and park. It is among my personally favorite locations for tourists and locals alike! Although if you’re planning a visit, be prepared to stand in line at the lobby by the elevators for there are always people wanting to visit this beautiful location. To avoid the lines, it’s best to come earlier in the day and on a weekday instead of weekend. The building which Cindy’s occupies is the Chicago Athletic Association hotel. It is quite the possibly a part of the best kept secret because not only does it have Cindy’s amazing rooftop bar, but it also has a few more hidden treasures worth the visit!
Inside the hotel on the second floor there is the James Beard award winning Cherry Circle Room connected to the Game Room. Like the light beacon from a lighthouse, the secret entrance is illuminated in the alley of Madison Street. The door is marked by a cherry like sign that leads to a stairwell into the Game Room entrance. The Game Room has a casual atmosphere with a fun variety of, as you can guess, games. The club vibe games include: Bocce ball, shuffleboard, foosball, cards and checkers to name a few. If you’re not into the games you can walk through The Game Room and leave the new world for the old. The new world melts into the old world at the Cherry Circle Room. The atmosphere changes from casual to a dark library-esque lounge with leather chairs, the kind of place to order and sip an Old Fashioned and/or enjoy a tastefully selected award winning dinner menu. The building itself has so much to explore and lends itself to drink hopping and exploring. Whether you go there for one or all of the lounges, Shake Shack or to see where the old pool used to be, the building itself is multi-faceted with many different pockets, each its own world offering an interesting visit. Observe and relax at the many worlds offered at the Chicago Athletic Association from the bottom to the rooftop.