The perfect blend of old-time tradition and swanky charm, Cindy’s Rooftop Restaurant is located in the Chicago Athletic Association hotel. The food, ambiance and social scene at the restaurant are great, but what makes this gem a top destination is the spectacular view of the city from the restaurant’s outdoor patio.
Unlike other iconic spots in the city, Cindy’s offers a view that encompasses Millennium Park, Maggie Daley Park, the Art Institute Museum and the iconic city skyline – all from one vantage point. Whether I’m enjoying the summer weather at brunch or escaping the cold for warm spirits indoors, I always make sure to spend time at the restaurant’s outdoor fire pit and lounge to take in the beautiful city view.
Though little can compare to such city views, the atmosphere indoors doesn’t disappoint. The space is enclosed with dome-window ceilings, allowing for natural sunlight to highlight the wood furnishings and natural décor, making the venue a warm, inviting atmosphere to enjoy the delicious food and drinks served.
For Sunday brunch, my friends and I usually order one of the sharable platters, along with a round of mimosas. If we’re there for lunch, we’ll likely share a few appetizers and entrées – our favorites being the Shrimp a la Plancha to start and the Lobster Roll or Seasonal Vegetable Torchio to share. For drinks, the restaurant offers a mix of elixirs and “potions”, as they call them – all of which add to the flavor and flare of this Chicago hot spot.