photo credit: Sandy Noto

Cindy’s image



LoopMagnificent Mile

$$$$Perfect For:Big GroupsBrunchBusiness MealsDrinking Good CocktailsEating At The BarImpressing Out of TownersOutdoor/Patio SituationPeople WatchingPrivate DiningSee And Be Seen

Included In

You Divvy’d around the lakeshore, squeezed your butt into a tiny chair at Second City, and took Snaps, Instas, and profile pics at the Bean. What’s left to show your high school crew who are from out of town? How do you appease someone who clearly wants to check off all 20 items on “Top 20 Things in The Windy City!” How do you impress Rebecca, who continuously reminds you that Chicago just doesn’t compare to that one summer she spent in New York? All signs point to Cindy’s.

The location (in the midst of throngs of tourists), the wait (anywhere from 15 minutes to an hour to get into the elevator alone), the reservations (or lack thereof for groups under four) - are all irritating. It’s loud, busy, and the crowd can be slightly obnoxious. But you’re willing to put up with some pretty annoying sh*t for for the best view in town. In the Chicago Athletic Association hotel on Michigan Avenue, Cindy’s is one giant greenhouse with communal seating, a large over-crowded bar, and the crown jewel - the patio. When you step out on that magnificent overhang, it’s suddenly all worth it as you take in the sun setting over Millennium Park. Plus, this deck is good almost year-round due to some strategically placed fire pits and heaters.

Cindy’s image

Foodwise, expect a good enough meal, but know you’re not really there for the food. The dinner menu consists only of large platters and sides, which isn’t always practical even if some items come in half portions. And when you add that to the unpredictable waits and inordinate level of noise, Cindy’s is only practical for certain situations like happy hour drinks, boozy brunches, and showing off to your out-of-town friends. But man is it perfect for those occasions. Our favorite situation is to go to Cindy’s early for a cocktail, head downstairs to the ground level Shake Shack for food, and then move to the mid-level Game Room for some bar games and follow-up drinks.

Make sure to set your expectations properly. But your friends will be happy if you save them from the $22 Sears Tower ticket and put it towards a cocktail here instead.

Food Rundown

Crunchy Lettuces

Crunchy lettuces and veggies bathed generously in a creamy, peppercorn dressing. Heavy-handed on the dressing, but still tasty.


Good burrata with a lot crusty bread. The candied pecans and melon are a nice touch. Get it.
Cindy’s image

Stone Ground Grits

Thick, creamy grits with undercooked cherry tomatoes and balsamic. A nice side to share with the group.

Pan Roasted Scallops

Scallops aren’t really built for sharing, and that’s still true here despite the fact this is meant to be a shared scallops platter.

Crispy Potatos

Basically a side of truffle fries. Get them.

Shellfish Platter

A quality shellfish platter with lobster, shrimp, oysters, and crab legs. If you’re sharing with a group, the $50 or $100 options aren’t a bad idea.

Double Cut Pork Chop

It’s not real Chicago if it’s not pork. This one comes with eggplant and a sherry vinaigrette. Not great, not terrible, but filling and a safe bet.


In any form, forgettable. We’ve tried both fried and roasted, and neither impressed. Your money is better spent on another cocktail.
Cindy’s image


Brunch is always a great time to go, as long as you have all the time in the world and nowhere else to be. Nineteen dollars for eggs benedict is expensive, but remember, you’re partially paying for the view.

Apple Cider Funnel Cake

If we could funnel ourselves right inside this cake with bourbon vanilla parfait, apple butter, and salted caramel, we would. It’s an excellent dessert.

Included In


Suggested Reading

Woodwind image


Woodwind is a small plates restaurant on the 18th floor of a high rise in Streeterville.

Francois Frankie image

Francois Frankie is an all-day French restaurant in the Loop with a rotating carousel bar.

Stocks and Blondes image

Stocks and Blondes is a bar in the Loop.

Raised  image

Raised is a rooftop spot in the Loop with a view of the river.

Infatuation Logo


2024 © The Infatuation Inc. All Rights Reserved.
The views and opinions expressed on The Infatuation’s site and other platforms are those of the authors and do not reflect the official policy or position of (or endorsement by) JPMorgan Chase. The Infatuation and its affiliates assume no responsibility or liability for the content of this site, or any errors or omissions. The Information contained in this site is provided on an "as is" basis with no guarantees of completeness, accuracy, usefulness or timeliness.


Get it on Google PlayDownload on the App Store