Cindy's Rooftop — Restaurant in Chicago

Cindy's Rooftop: A Haven Above the City

Nestled atop the historic Chicago Athletic Association, Cindy's Rooftop is more than just a dining experience; it's a picturesque escape from the city's relentless pace. As you step out of the elevator onto the 13th floor, you're greeted by an ambiance that's both chic and inviting, a rare find in the heart of downtown Chicago.

The open-air terrace offers a breathtaking panorama that stretches from Millennium Park to the vast blue expanse of Lake Michigan. It's a view that can only be described as one of the city's finest, transforming a simple meal into a visual feast.

But Cindy's is not just about the view. The menu, crafted with a nod to Executive Chef Kaleena Bliss's Pacific Northwest roots, offers a seasonal array of dishes that are as fresh as they are flavorful. From the brunch offerings to the late-night bites, each plate is a testament to the kitchen's commitment to quality.

The service at Cindy's matches the excellence of its cuisine and views. Attentive yet unobtrusive, the staff ensures that your experience is seamless from start to finish. Whether you're there for a casual brunch or a special dinner, you feel welcomed and valued.

And let's not forget the cocktails. The bar at Cindy's is a destination in its own right, with creative concoctions that perfectly complement the menu. Each drink is a blend of art and science, with seasonal ingredients that make every sip a new discovery.

Cindy's Rooftop is not just a restaurant; it's a destination that offers a unique perspective of Chicago. It's a place where memories are made, whether you're a local or just passing through. It's a reminder that sometimes, the best way to appreciate a city is from above, with good food, great company, and a view that's second to none. Cindy's Rooftop is a must-visit for anyone looking to experience the best of Chicago's...

I've been here twice and had 2 different experiences.

The first visit was for a late night dinner. I was with my sister and did not have a reservation but we were promptly seated and despite it being right before closing, the service wasn't rushed at all. I had the best pesto gnocchi and was so excited to return and try something else delicious.

The second visit was also without a reservation but for lunch on a Friday. I had tried to make a reservation the morning of but there weren't any available. We had to wait in the lobby for about 15 min in the walk up line before being sent up to the restaurant level where there was a second host stand. This is where they take your phone number and give you the run down of your dining options (seating and menu types). I wish they would have done this at the first host stand in the lobby as the noise from the restaurant level made it difficult to communicate with the second host stand. My phone number must have gotten written down wrong because after waiting for 30ish more min I went to ask how much longer the wait would be and they said that they had already paged me and I'd have to wait as if I'd just gone up the elevator all over again for a table. At this point their lunch service had ended and they would only be serving drinks for the next 30 min until their bar snacks menu opened up. Their website hours don't mention this gap in food service, it's only when you click on each individual menu that you see which hours of the day are for each menu. I was hangry by this point so since we'd already seen the view and taken pictures while we were waiting we left and had a nice lunch at Acanto instead (I recommend!). Do your best to avoid the 2PM-2:30PM no food part of the day if you wanna...

A classic downtown wannabe “posh” place (as people seem to call it) with no refinement of any sort. This was my second time in many years and im not going back. With 3/4 of the tables being empty but reserved to ‘eating’ customers, and no other place to sit, we are kinda forced to order food. Ok…

The host shows us the 6-7 item snack menu to make sure we want to order sth, because there is no going back once we are honored with a table. Ok… I already said we’ll eat? One drink menu for four people, oh ok, I guess we’ll share.

But none of these prepared me to the culinary horrors that could fit into that small tray. We get chips and white bean roasted garlic dip. We need to order extra crackers on the side bcs the dip only comes with seasonal vegetables, which turn out to be celery, a very tasteless cucumber and raw string beans (!) seriously? The dip was the worst thing I tasted in a while, made me long for store bought ones. Chips pretty much looked like store-bought ones rolled in some nori crumbles. Zero originality. I guess the tiny bowl it’s served in should suffice to make it look cool.

As I need to pick up a phone call in a silent spot, I ask one of the waiters if I can take a call in one of the empty areas. He suggests that I can use one of the bathrooms downstairs because all areas are reserved for events not starting in the next two hours. 🤯

Apart from this interaction, the wait staff was nice, I really like that it’s so spacious and not super loud. But the rest of the experience simply lacked any value. With that said, I don’t really expect much from downtown places, but this was below my lowest...