What if I told you it was possible to have perfectly prepared blueberry pancakes, creatively prepared chilaquiles and much more while taking in stellar views of Millennium Park and beyond? And oh yes: there’s downtempo soul music carefully curated as well. It’s all possible and it happens every Sunday from 10am-3pm at Cindy’s on the 13th floor of the Chicago Athletic Association Hotel in the Loop.

Yes, it might seem to good to be true, but it is so very real. Since its opening last year, folks from Dubuque to Doha have been zooming up the elevator for drinks, shareable platters, and priceless terrace views.

The design aesthetic at Cindy’s is remarkable, and it includes repurposed woods, an elaborate backbar area that provides a cornucopia of color, and long wooden benches that are perfect for families or couples.It’s one of the touches that creates a fine mood for conversation and communion with others.

Cindy's Rooftop (bar) at Chicago Athletic Association Hotel

Cindy's Rooftop (beverages) at Chicago Athletic Association Hotel

Before tucking into some of their fine brunch entrees, you’ll want to pay close attention to their beverage program, which includes a host of cocktails curated by Nandini Khaund. I can personally recommend any of the hot chocolates (the perfect accompaniment on a cold winter morning) or the kombuchas. My personal favorites include the strawberry basil crabapple or the gentle sweetness of the raspberry-chocolate mint concoction.

Cindy's Rooftop (blueberry pancakes) at Chicago Athletic Association Hotel

In terms of main dishes, you’ll definitely want to order a few to pass along with friends and other culinary companions. The pancakes have the perfect consistency, and the Michigan blueberries combined with the blis barrel aged maple syrup are some of the best I’ve ever had. You don’t need much of that syrup, as a little goes a long way.

In terms of savory items, I’d also recommend the cast iron chilaquiles, which include Indiana corn, charred scallions, salsa verde, and pickled fresno chiles. Folks with a passion for fruits of the sea will want the elaborate shellfish platter, which features lobster, oysters on the half shell and king crab. Also, the salt and pepper biscuits are perfect for sharing, and the serrano honey has a bit of kick that makes these baked goods eminently memorable.

Cindy's Rooftop (DJ) at Chicago Athletic Association Hotel

The entire experience is made even more wonderful with the fine mixes of DJ Dave Mata (he brings the soul in this here soulful brunch) as he weaves his way through Motown favorites, deep dusties, and a mix of other musical excursions. Make sure and stop by and say hello and don’t forget to check out his amazing rings. He’s plied his trade as a music educator and talented DJ for years in Chicago and he’s quite a friendly fellow.



12 S. Michigan Avenue 13th Floor, Chicago, IL

  • Open for dinner, cocktails and Sunday brunch
  • Reservations are available for parties of four or more; private dining also available


Photos: Max Grinnell, Cindy's