Chicago is such a great city, and there are so many places to see and experience, whether you live here or are visiting for a few days. The one place I take every visitor to is CINDY’S ROOFTOP. It’s not exactly a “rooftop”, but it has a spacious balcony that overlooks the gorgeous Millennium Park. On a clear day, you see every aspect of the park as well as the blue Lake Michigan beyond it. While the view is amazing, you’re also there for the delicious food, creative cocktails and that signature photo opp. 🙂

I’ve been to CINDY’S many times, and have many photos of the meals and drinks I’ve had there, but here are 4 of my favorites.

SHELLFISH PLATTER | maine lobster, shrimp, oysters on the half shell, king crab legs, white balsamic mignonette, lemon & tobasco


Need I say more about a seafood platter? It’s an indulgence and Cindy’s has the right amount of each component; all extremely fresh!

SHRIMP A LA PLANCHA | charred scallion and marcona almond pistou, sweet garlic puree, grilled lemon


This is easily my favorite dish on the regular menu. The prawns are perfectly seasoned and come bathed in a garlic-y sauce that’s just made for dipping the grilled bread in as well. There are 6 to an order, and I while I usually share it among other dishes, I could absolutely have this on my own. I end up asking for more toast points so none of that yummy sauce goes to waste.

[TIP] You can order anything on the menu from the Torchio entree up as a half order.

WESTERN CAPE | fields of france rooibos-infused absolut elyx, crĂšme de pĂȘche, rare tea cellar’s demerara-ginger syrup, lemon, soda


My favorite cocktail at Cindy’s also happens to be an homage to my homeland, South Africa. It’s a rooibos tea base, and basically a South African version of the Moscow Mule. You’ll love it.

Lastly, if you’re at Cindy’s for a weekend brunch, do yourself a favor and try the Matcha Latte. Yes, matcha has been a trend over the last couple of years, and while it obviously makes for a great photo, the latte itself is stellar. A great buzz to start your day!

MATCHA LATTE | with almond milk


These views though…


If you haven’t been yet, local or visitor alike, add CINDY’s to your list of stops! It’s also in the Chicago Athletic Association hotel, which is gorgeous in itself. So roam around the hotel’s library or game room, maybe have some Shake Shack if you’re in the mood, and make your way up to Cindy’s for a cocktail and amazing views.

CINDY’S ROOFTOP | 12 S Michigan Ave, Chicago, IL 60603

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