Cindy’s Rooftop


Who: Cindy’s Rooftop

What: A rooftop restaurant and open-air terrace with panoramic views of Millennium Park

When: Monday to Friday 11am-2am, Saturday 10am- 3am, Sunday 11am-12am

Where: Inside of the Chicago Athletic Association Hotel at 12 S Michigan Ave, Chicago, IL 60603

Why: The Chicago Athletic Association Hotel has a deep rooted history in the city of Chicago, and was built around 1890. “Membership was available only to the most elite Chicagoans who had to be voted in by existing members, making the experience an exclusive one. It’s no wonder, then, that the Association’s founding members included names like Marshall Field, Cyrus McCormick, and William Wrigley, who later adopted the club’s C-shaped logo for his newly-purchased baseball team, the Chicago Cubs.”

It has a very unique and interesting story, built by a famous architect, it operated as a mens only club and was established as a Chicago landmark. Needless to say, this place is famous. In 2007, the athletic association closed it’s doors. Only to be purchased by hotelier John Pritzker, AJ Capital Partners LLC, and Geolo Capital with plans to turn it into a luxury hotel. They intended to keep the name and to preserve and restore the hotel to it’s original beauty and that is exactly what you’ll see when you visit her now. 

We stayed across the street in a different hotel, but were told about Cindy’s Rooftop by a few different people. So it didn’t take a lot for us to make our way over, and up the elevator 13 stories to the elusive rooftop bar and restaurant. Next time I go, I’d love to eat there, but this time we only had time (and an appetite) for drinks. 

The space is beautiful, with big floor to ceiling windows looking out towards Lake Michigan, and the windows in the roof making it feel like it’s open to the sky, it was just perfection. We made our way over to the bar to grab a drink before we dashed to the outside patio. 

The drinks were fairly pricey, but we considered it the price to hangout at such a popular establishment and they were appropriately strong. It was Sunday around 1pm and the place was packed. I ordered a Kick in the Daisy, made with avion reposado, ancho reyes, licor 43, fresh watermelon, lime, and maldon sea salt. My sister had the Howl at the June, made with citadelle gin, ‘jun’ kombucha, grapefruit, and sparkling rosé. They were just what the doctor prescribed, fresh, flavorful, aromatic, and strong. 

We took our drinks straight to the patio and found a spot nestled at a stand-up table overlooking Millenium Park. It was bliss!

We had such a fun time looking at the city from this vantage point. You can see Lake Michigan, Cloud Gate ( the famous bean!), Grant Park and Millenium Park, and the sailboats in the harbor. It really is a special restaurant nestled right off Michigan Avenue with million dollar views. This is one place you have to see to believe. 

I can’t wait to go back, and hope when you go you’ll let them know Dine With Shayda sent you! And follow my daily food adventures on Instagram and Snapchat at @DineWithShayda.