Photo by Nick Gerber, courtesy of Cindy’s

The One Who Keeps the BookChicago

How to Get Into Cindy’s, Chicago’s Most Epic Rooftop


Opened in 2015 on the roof of the Chicago Athletic Club Hotel and boasting epic views of Millennium Park, Lake Michigan, and the Chicago skyline, Cindy’s Rooftop has quickly become one of the city’s hardest-to-nab reservations. On any given weekend, it’s near-impossible to grab even a drink at the bar, as many guests have made dinner reservations months in advance. After temporarily closing during the pandemic, Cindy’s reopened this spring and hasn’t missed a beat since.

Welcome back to another installment of The One Who Keeps The Book, where we give you the keys on getting in to some of the city’s most popular spots. This time, we’re chatting with Cindy’s general manager Lindsay Bolster on what to eat, drink, and how to snag a table at the most talked about (and Instagrammable) restaurant on Michigan Avenue. 

Resy: How many seats are at Cindy’s? 

Lindsay Bolster: There are 103 seats in Cindy’s, but only 42 bookable seats online, which comes out to 12 tables.  We have 15 bar stools, and while there are 26 seats in our library and private dining room, they are usually booked for private and semi-private events.

Then, of course, there are the couches that face the lake–which can’t be booked online–but they add an additional 20 seats. 

Behold, Lake Michigan!
Behold, Lake Michigan!

How many covers do you do on a given night?

For brunch, we’re doing about 250 covers, and for dinner, probably around 350–excluding bar seats. 

When do reservations drop? 

If we’re opening up reservations for a Friday (which is 30 days out), every single reservation will be booked that same day. No exaggeration–as soon as they’re released, they are booked. We’re saying Mondays are the new Thursdays, and those are booking quickly, too. Brunch during the week takes a little bit longer to book, but I would say the day that reservations are released for a weekend, whether it’s brunch or dinner, they’re booked immediately because again, there are only nine bookable tables online. 

We give our sales team up until a week before to book private dining spaces, and if they don’t, that’s when we release that seating, too. So that’s a little trick of the trade. 

What’s the busiest night? The least busiest night? 

I would say Tuesday and Wednesday nights are the quietest. And I think the same goes for brunch, which we now serve seven days a week. Again, if you’re looking to get a weekend reservation, especially for a large party, just look at your calendar 30 days out — those are released at midnight. 

How long is the usual Resy Notify list? 

It could be upwards of 500 people on any given day, and people show up that are on that Notify list thinking it’s an actual reservation. So that can get a little tricky for us in our host team.

Are any seats held for walk-ins? 

We highly encourage reservations but there is an opportunity to walk in. Your best opportunity would be to come right when we open for brunch or right when we open for dinner (we start serving dinner at 5 p.m.). If you come right when the bar opens, we also have four countertops in the corners of the dining room, and we reserve those for walk-ins. But we will prioritize hotel guests.

How long is the wait-list for walk-ins? 

If we can’t seat you when you walk in, we’ll put you on a waitlist. We can’t quote a time. And we can’t quote whether or not you’ll be guaranteed to be seated before brunch is over. But we do work our way through a good amount of the waitlist and are able to seat people.

If I’m flying solo, how likely is it for me to pull up to the bar (without a reservation) and order a glass of Albarino and oysters by the half shell? 

I love that–Albarino is my favorite, by the way. You know, there’s a good chance. If you’re patient and you want to sit at the bar and eat, you might have to wait maybe 10 to 15 minutes for somebody to close out their tab. And we do allow up to three people standing behind anybody who’s seated. We don’t want guests sitting at those high top tables to feel like their spaces are being infiltrated. When it starts to get too crowded, that’s when we’ll start a line downstairs. We don’t start the line to make ourselves look exclusive or anything like that; it’s to take some pressure off the bartenders so they don’t see a sea of people flagging them down.

What would you say is the best seat in the house? Can someone request that specific table, or their favorite table? 

Looking through our Resy reservations, I would say 50 percent of them have a note saying a table with the “best view.” Unfortunately, regular diners don’t always understand that you can’t walk into a restaurant and pick your table. We have this strategically plotted so that one server doesn’t get overwhelmed and the other standing around doing nothing.

The best seats in the house, I would say, are those couches that face the windows and the lake. But with that the challenge is that it’s a lower table to couch setup — it’s like sitting at home, eating on your couch at a coffee table, which might be a little uncomfortable for some. But a lot of people are willing to make that sacrifice to sit at an awkward table and get that prime view. As far as the worst seats go, there are three that are terrible: the two countertops that face a brick wall, and the one table in the library that faces a pillar. 

The cuisine at Cindy’s is described as ‘New American’ with seasonally-rotating, family-style comfort food. How often does chef Christian Ragano change the menu, and what are some dishes guests can expect to see? 

If Chef had his way, he would change the menu every month. We change it at least two times a year, and usually four times a year with a complete overhaul of the dishes. In between that time, we might just swap out a couple of ingredients and some of the dishes. We focus on local producers and purveyors, really shining a light on produce from the Midwest. 

Oysters will always be on our menu, and there will always be a chicken, fish, and meat dish. We’ve also started to incorporate a lot more vegan and vegetarian dishes. And for brunch specifically, we will always have chilaquiles, as well as aguachiles, to honor chef Trace, a sous chef who helped open Cindy’s, but unfortunately died in 2020 due to gun violence. 

Okay, so my friends and I have been able to snag a four-top on an early Saturday dinner before catching a show at the Goodman Theater. What should we absolutely order to eat and drink? 

I definitely encouraged sharing different dishes. If this is a dinner experience, get some oysters and burrata for the table to start. I’d then order the whole fish with a few of the seasonal sides as well as the chicken thigh. I would ask for a large format cocktail (we call them apothecaries), then you can self-serve at the table.

Are there any exciting new things happening at Cindy’s Rooftop right now?

We brought back DJ Will Galvin for Sunday brunch, and he plays all soul music from 11 a.m. to 3 p.m. It creates a really fun environment. Not like a club or a total party, but it helps to elevate the vibe overall. 


Chasity Cooper is a writer and wine culture expert. When she’s not traveling, you can find her exploring the newest cocktail bar or restaurant Chicago has to offer. Follow her on Twitter at @bychasitycooper. While you’re at it, follow @Resy, too.