Brunch Bucket List: Meet Us At Cindy's Rooftop
When you talk about Sunday mornings, they sound hopeful — radiant even! In your mind, each and every time, they’re sunny blocks of free time, seemingly conjured up out of voodoo, where exploration is possible and adventure...
by Jake Kilroy

When you talk about Sunday mornings, they sound hopeful — radiant even! In your mind, each and every time, they’re sunny blocks of free time, seemingly conjured up out of voodoo, where exploration is possible and adventure is inevitable. They carry a weight in your heart and a (mild) delusion in your mind that you can, if only for a few hours, return to the endless sunset skies of your summertime youth. 

Enter the soul-reviving wonderland that is brunch, and welcome to this week's Sunday #BrunchBucketList. Today, we dine, dream, and do it up properly at the newly opened Cindy’s Rooftop.



Rooftop Brunch Vibes

Rooftop atmospheres suit brunch, as a breeze cruises through like the eatery best-dressed regular and and the horizon seems very much part of the matinee. At Cindy’s Rooftop. in Chicago, morning-after rituals come into play at a rooftop restaurant and open-air terrace that treats diners to panoramic views of Millennium Park, the Art Institute, and Lake Michigan. 



The charming cafè, practically the crest of Chicago, welcomes sunshine from what feels like the top of the world. It’s the jewel in the crown of The Chicago Athletic Association Hotel, a stunning edifice where, in the 1890s, male-only members of the athletic club worked out and (assumedly) twisted their moustaches. Now a stylish boutique hotel, the chic getaway keeps its breathtaking sky-filled hideaway above Michigan Avenue, where it has the unmistakable look of having always been there. 



Windowed ceilings, exposed-brick walls, and fashionable lighting make for a modern host of a brunch spread, but with the relaxed ambience of a Great Lakes beach house and the familiar atmosphere of a dinner party for old friends, all of whom brought recent eager transplants to the city, Cindy’s Rooftop is all the right vibes in one cooked-up masterpiece—chic yet casual and comfortable. The menu takes poetic note from its dapper surroundings and offers au courant dishes without any of the hypebeast bark.



Bring your Militia of Maids

So let’s assume your crew isn’t some well-to-do batch of moguls, tycoons, and socialites, and you don’t all have high-class interiors in a high-rise lofts with highly touted views. Otherwise, you could have your crowd of chefs bring you and your lot a feast for the simple holiday that is Sunday Morning with your militia of maids left to tend to clean-up. Given such a lack of windowed empire in the Windy City, Cindy’s Rooftop is the closest venue to offer up the vibrant vibe of a big-city lounge with a world-class view. 


Photo: @megendisanto 

Brunch Sunrise Potions, Elixirs, Tisanes, and Mocktails

Promising to cure your ills with creations from the bar, "the original pharmacy" as the menu reminds you, harkening back to its broad-shouldered and bearded origins, the boozy concoctions will turn your liver into a ballroom and your mouth into a garden.

Take (down a few helpings of) the dusty lavender-colored Grey Garden, a vodka-based headliner, swirled and ready to stun with Dolin Blanc, crème de violette, Emperor's Jasmine Pearl Tea, and lemon. If you roam town with a posse, Cindy’s generously offers Apothecary Service, so 20 of you late-morning wildcats can turn your gut into a drunken farm with the Grey Garden. Cindy’s Rooftop also does large-format servings of The Hesitant Elephant, named for an elephant that wouldn't leave the old-timey athletic club's annual circus at the turn of the century. It’s Rittenhouse Rye batten-down with Sailor Jerry Rum, Averna, Campari, Letherbee Bësk, and cold-brewed coffee, topped with Edmund Fitzgerald Porter.



If you’be got a booked-up Sunday afternoon ahead, following your rise-and-truly-shine escapades, then maybe a good dive into the grand drink isn’t a specialty you’re on the lookout to down. Cindy, bless her namesake idyll , hears you. That’s why the menu pops and rolls with a downplay of drink, from its ancient health tonics of fermenting sweetened teas to mulled cider that's a fervent festival of flavor, given the tasty appearances of apple, cinnamon, clove, pecan, star anise, and ancho chile at the same party. Don’t worry, though, if your plans suddenly get canceled and the magic hour of brunch stretches its beloved reach into your day, you can always turn your mocktail into a potion by way of rum or gin.


Photo: @mksportsanista


Chicago’s Class-Act Cuisine

Guided by Executive Chef Christian Ragano, creator of Glencoe’s much-loved Guildhall and former Chef de Cuisine at NoMi, this restaurant’s celebrated menu of fresh seasonal cuisine enraptured guests, Backed by Chef de Cuisine Heff Arasi and renowned Spirit Guide Nandini Khaund, the brunch haven invites foodies for large-format-style dining, complemented by cocktails and apothecaries. 



Currently Craving

Brunch platters—consciously built for sharing between a handful of hungry locals—make good on their promise to squash any appetite, with them ranging from classic Lox and Bagels or Granola and Yogurt Parfaits to the new wave outings of Cast-Iron Quiche Lorraine or Croque Madame. In fact, word on the street has it that you MUST TRY the following pairing: 

Cast Iron Chilaquiles with the Beer for Breakfast, made with strawberry syrup, fresh orange, and local Eille saison (pictured above) - yum!



Whether you spent your Saturday night in with a book or bonked out at a blissful bash, you’re coming into Sunday morning with need of reward or redemption. If you’re anywhere between the beating heart or outskirts of the Windy City, head to The Chicago Athletic Association Hotel and go straight to the top. Cindy’s Rooftop will be waiting for you.

Wanna meet us there?



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