Cindy's Rooftop Restaurant Chicago

Trendy scenic bar

Sydney from Chicago

About me I am a Chicago native best defined for my curiosity and willingness to explore. I value uniqueness and quality, which attributes to my appreciation for the city and for the entertainment it provides. With a close-knit set of friends and family nearby, I am often exploring the areas around me with peers by my side. Whether it’s through travel or leisure activities, I am...
""Cindy's Rooftop Restaurant" on Chicago Athletic Association hotel has great food, ambience and a social scene, but I just love the rooftop views the most."

The perfect blend of old-time tradition and swanky charm, Cindy’s Rooftop Restaurant is located in the Chicago Athletic Association hotel. The food, ambiance and social scene at the restaurant are great, but what makes this gem a top destination is the spectacular view of the city from the restaurant’s outdoor patio.

Unlike other iconic spots in the city, Cindy’s offers a view that encompasses Millennium Park, Maggie Daley Park, the Art Institute Museum and the iconic city skyline – all from one vantage point. Whether I’m enjoying the summer weather at brunch or escaping the cold for warm spirits indoors, I always make sure to spend time at the restaurant's outdoor fire pit and lounge to take in the beautiful city view.

Though little can compare to such city views, the atmosphere indoors doesn't disappoint. The space is enclosed with dome-window ceilings, allowing for natural sunlight to highlight the wood furnishings and natural décor, making the venue a warm, inviting atmosphere to enjoy the delicious food and drinks served.

For Sunday brunch, my friends and I usually order one of the sharable platters, along with a round of mimosas. If we’re there for lunch, we’ll likely share a few appetizers and entrées – our favorites being the Shrimp a la Plancha to start and the Lobster Roll or Seasonal Vegetable Torchio to share. For drinks, the restaurant offers a mix of elixirs and “potions”, as they call them – all of which add to the flavor and flare of this Chicago hot spot.

028-beach-bar-1
Bars
021-spoon-and-fork-1
Restaurants

This week 25% off

with the code fall25

*on our yearly membership

Chicago Spotter Sydney

About me I am a Chicago native best defined for my curiosity and willingness to explore. I value uniqueness and quality, which attributes to my appreciation for the city and for the entertainment it provides. With a close-knit set of friends and family nearby, I am often exploring the areas around me with peers by my side. Whether it’s through travel or leisure activities, I am always looking for the next opportunity to discover my surroundings and enjoy the entertainment and livelihood I find. Why Chicago? Having lived in Chicago my entire life, I am a p...

About this spot

12 South Michigan Avenue

Shrimp:

USD

15

3127923502

Oct 2, 2025

Our Chicago City Guide

Find your way with 116 Insider Tips from our Local Spotters

Discover hidden gems and all our locals’ favourites! Get full access to our Chicago guide.

Loved it? Join us!

Loved this Spot?Join your international community. Share your favs and become part of our international community!

Nice place right!? There’s so much more to discover:

Discover all other hidden gems in Chicago

FLW Home & Studio

Architecture of the ages

Step into Frank Lloyd Wright’s first project in Oak Park — an inspiring tour through the birthplace of the Prairie Style, just off Chicago’s Green Line.

002-building
Art & culture

by

Sophie

Amado

Nov 11, 2025

Wormhole

Time-traveling coffee shop

Wormhole in Wicker Park, Chicago is my favorite coffee shop in the city. When you walk in, it feels like you have stepped back in time to the '80s...

020-coffee-cup-1
Coffee & tea

by

Sophie

Amado

Nov 10, 2025

Will's Northwoods Inn

Wisconsin in Chicago

Will’s Northwoods Inn brings Wisconsin charm to Chicago with Packers pride, fried appetizers, quirky decor, and a moose-topped patio near Wrigley Field.

028-beach-bar-1
Bars

by

Sophie

Amado

Nov 10, 2025

Side Street Saloon

Dive bar with pizza

Side Street Saloon in Lakeview is the perfect no-frills dive bar with a cozy Italian vibe in back, great pizza, pool, and a quirky neighborhood charm.

028-beach-bar-1
Bars

by

Sophie

Amado

Nov 10, 2025

Christkindlmarket Chicago

German Christmas market

I've been going to the Christkindlmarket Chicago for as long as I can remember. I definitely recommend visiting on a weekday!

002-building
Art & culture

by

Sophie

Amado

Nov 10, 2025

Tesfa Ethiopian

East African comfort food

The food here is prepared by Moses Sake, chef and co-owner of Tesfa, who learned how to cook from his mother. He runs Tesfa with his brother, Samuel Sake.

021-spoon-and-fork-1
Restaurants

by

Lydia

Schultz

Nov 8, 2025

Mella Cafe

Local spot for Eritrean food

I recommend getting the traditional breakfast combo, a sampler with three dishes, that comes with complimentary warm, crispy bread!

021-spoon-and-fork-1
Restaurants

by

Lydia

Schultz

Nov 8, 2025

De Luna Taco Grill

Spicy Truck Tacos

The star of the show is De Luna's "volcano" taco, made with spicy poblano pepper and melted cheese. It may be one of the best tacos I've eaten in my life!

021-spoon-and-fork-1
Restaurants
024-burger-1
Snacks

by

Lydia

Schultz

Nov 8, 2025

Nhà Hàng Vietnam

Traditional Vietnamese

Although this street is dominated by Vietnamese eateries, Nhà Hàng is a quieter, no-frills joint as opposed to the touristy, upscale restaurants nearby.

021-spoon-and-fork-1
Restaurants

by

Lydia

Schultz

Nov 8, 2025

Irazu

Chicago's Only Costa Rican

Here diners sit in the naturally lit patio while enjoying traditional homemade Costa Rican food: sweet plantains, grilled veggies, rice and beans.

021-spoon-and-fork-1
Restaurants

by

Lydia

Schultz

Nov 8, 2025

Bolivar & Lincoln

Venezuelan Haven

My favorite thing to order here is the vegetarian arepa, which is stuffed with black beans, a generous portion of avocado, and sweet plantains.

021-spoon-and-fork-1
Restaurants
024-burger-1
Snacks

by

Lydia

Schultz

Nov 8, 2025

Superdawg Drive-in

Classic Chicago hot dog spot

Founded in 1948, "Superdawg" is THE quintessential Chicago hot dog place - they'll bring your order right to your car, like they did in the '50s!

021-spoon-and-fork-1
Restaurants

by

Sophie

Amado

Nov 1, 2025

Heading to Chicago?

116 Insider Tips from our local Spotters

Authentic Stories by Real People

Escape the Crowd & Travel Slow 🐌

... for just €9.99

Chicago app Home
Chicago app Home
Chicago app Map
Chicago app Home

Heading to Chicago?

0 Insider Tips from our local Spotters

116 Insider Tips

✓ Escape the Crowds

✓ Find Spots nearby

✓ Authentic Stories

... for just €9.99

City guides by those who know the city in and out!

Our Locals' Favorite Bars

Our team loves Chicago

Get to know our other Spotters from Chicago

As featured on:

New-York-Times
the-guardian
mashable
the-sunday-times
[paywall_activator]
false
0
false
71
Made with the 💚 of 496 Spotters.
Filters