LoopThe literal crown jewel of the recently renovated Chicago Athletic Association not only offers some of the best views of Millennium Park, it also shakes up some of the area’s finest cocktails for both indoor and outdoor consumption. The multi-page menu is a treat in itself, listing cheekily titled tipples like Right on Thyme (Pau Maui vodka, Bigallet Thym Liqueur, Rhum Clement Coconut, cream sherry, blueberry, lavender, lime, saba, Lagunitas Hoppy Water) and Grandma's Candy (Lapostolle XO pisco, St. George Spiced Pear, Manzanilla sherry, lime, miso, Peychaud's) alongside colorful little illustrations. As for food, brunch is big business in these parts, when hearty best-sellers like chorizo-laden chilaquiles, rich biscuits and gravy, and chicken and waffles take center stage.

A constant bustle of locals, tourists, and suburbanites pervades Cindy's terrace at the Chicago Athletic Association hotel, which has some of Chicago's most spectacular views over Millennium Park, the Art Institute, and Lake Michigan. The cocktails make clever use of fresh produce, juices, kombucha, tea, and interesting spirits, resulting in drinks that are refreshing, inventive, seductive, and overall delicious. No matter if you want to come with family for a nice lunch or bring a date for late-night cocktails on the terrace, this is an all-purpose spot for locals and visitors.

A stylish rooftop bar and restaurant atop the Chicago Athletic Association Hotel. Why we love it: Whenever we want to impress out-of-towners, we book a table at the Chicago Athletic Association Hotel’s 13th-floor rooftop bar, from which Millennium Park, Lake Michigan and the city skyline are on glorious display under a glass atrium. The drink lineup complements the vistas with easy-sipping selections that are best enjoyed in the sun—like Trouble Will Find Me, made with tequila, mezcal, watermelon, and yuzu soda.

For unrivaled views of Chicago’s best sights, head to rooftop bar Cindy’s for its sweeping take of Millennium Park and “The Bean,” Pritzker Pavilion, and the expansive lakefront. Cindy’s offers its entrées in two different sizes: the half portion is intended for one or two people while the full portion is meant to be shared with three to four people. Executive chef Christian Ragano relies on independent purveyors to inform his New American menu (with options like Porterhouse Au Poivre for Two).

Cocktails are always the way to go at Cindy’s, a rooftop bar high above the Chicago Athletic Association Hotels. During the warmer months when the firepits are not in use, everyone spills onto the outdoor section – where there are unobstructed views of Millennium Park and The Bean – clutching highballs and piña coladas. The food menu is just as expansive as the bar itself, and on weekends brunch is served, with stacks of buttermilk pancakes and chilaquiles flying out of the kitchen.

Cindy’s in the Loop has one of the best panoramic views of everything that makes this city great. It’s located on the roof of the Chicago Athletic Association Hotel, and because this place is incredibly busy there can be an hour-long wait just for the elevator. But once you’re upstairs, you’re rewarded with an unbeatable view of the illuminated skyscrapers (during the day, the twinkling skyline is traded for the beautiful view overlooking Millennium Park and Lake Michigan).

A self-described “glass atrium overlooking Millennium Park,” Cindy’s at the Hyatt's Chicago Athletic Association has some of *the* best view of the city, according to the patrons who love it—especially if you happen to be seated on the outdoor terrace. While lines are fairly common here without a reservation, once you’re in, you’ll be treated to relaxing concoctions, like the Citrus Party CBD soda, and refreshing bites, à la oysters on the half shell. You can also indulge your inner big kid post-dinner with Executive Chef Christian Ragano’s Grasshopper ice cream sandwich of chocolate mint ice cream and chocolate.

On top of the Chicago Athletic Association Hotel, Cindy's continues to be one of the hottest spots since it opened in 2015—much due to the sprawling views from the terrace overlooking the lake, Millennium Park and the Art Institute. While people come for the views, they stay for seasonal, local cuisine and inventive cocktails, which incorporate fresh juices, kombucha, high-end tea and drinking vinegars. Insider tip: Reservations open 30 days in advance and book up early, but Cindy's stays open between lunch and dinner, so snagging a table eases up midafternoon.

Visiting Cindy’s is a must for those with even a passing interest in Chicago hospitality. “I love Cindy’s at the top of the Chicago Athletic Association,” says Ari Bendersky, writer and author of the Something Glorious with Ari Bendersky substack. “The view overlooking Millennium Park and Lake Michigan is unparalleled and shows locals and visitors a glimpse of the city’s history while also soaking up all its beauty.” Bendersky recommends starting with oysters and a cocktail like an Oaxaca Old Fashioned or a glass of crisp dry Provençal rose.

Enjoy the panoramic views of the Millenium Park, sparkling Lake Michigan, and The Art Institute of Chicago from Cindy’s open air terrace. Serving food and drinks sourced from local ingredients, executive chef Christian Ragano and his team will provide you family style comfort food and award-winning cocktails. The bright, tropical, and crisp Spontaneous Publicity cocktail made with leblon cachaça, bacardi superior rum, bénédictine, lemongrass, and lemon is one worth trying from a series of different concoctions at the bar.

This glass atrium bar in the Loop in downtown Chicago is perched on the 13th floor of the Chicago Athletic Association Hotel, across the street from Millennium Park. Cindy’s rooftop restaurant offers some of the best views of the park, and as a bonus, you can see Lake Michigan from here, too. The bar got a design refresh in early 2024, with a new layout and seating suitable for both intimate and large parties, timed with executive chef Kaleena Bliss’ appearance on Top Chef: Wisconsin.

Cindy’s Rooftop is, without a doubt, the perfect spot to go for dinner or appetizers on a Chicago rooftop with a stunning view of Millenium Park and Lake Michigan. With a modern and roomy glass atrium lounge and an outdoor rooftop terrace, this lively rooftop restaurant and bar is available all year round for lunch, dinner, and even weekend brunch. Presented by executive chef Christian Ragano, you can savor a wide variety of traditional comfort foods from around the world.

There is a good reason Instagrammers flock to Cindy’s, and that’s the sweeping views of Millennium Park that can be enjoyed from the unique rooftop. Self-described as “the jewel in the crown of the Chicago Athletic Association”, the rooftop restaurant and its open-air terrace were once an exclusive club owned by wealthy Chicago businessmen. Back then only special members could enjoy the extreme extravagance and you can see within that the elegance has not faded one bit.

Cindy’s Rooftop is one of those rare restaurants that’s a hit with both tourists and locals looking for a great night out. The beautiful space — located on the rooftop of the Chicago Athletic Association Hotel — has a covered, spacious inside area and a terrace offering unbeatable views of Millennium Park. The restaurant serves lunch, dinner and a weekend brunch, with classics like oysters, roast chicken, branzino and so many delicious desserts, you’ll want one of each.

One of the most popular and famous Chicago rooftop restaurants, Cindy’s is perched atop the Chicago Athletic Club building overlooking Millennium Park, making it a great spot to enjoy a birthday dinner in Chicago with an amazingly expansive view of the skyline, park and lakefront. It’s a popular spot in the summer, where they have an endless selection of signature cocktails and boozy popsicles, as well as a menu with elevated large and small plates.

Cindy’s is a restaurant and bar on the rooftop of the Chicago Athletic Association Hotel located near Millennium Park. Make sure to spend some time outside on its famous open-air terrace which offers panoramic instagram worthy views of Millennium Park and Lake Michigan. This is a popular spot due to the amazing views and the wait for the elevator can be long but if you visit around the time it opens you can enjoy the great views without the crowds.

The FAQ page on their website states that guests of all ages are welcome at any time and are able to enjoy non-alcoholic beverages at any time. Cindy’s Rooftop is a popular rooftop restaurant located in the Chicago Athletic Association Hotel building in Chicago, Illinois. The bar is situated on the 13th floor of the building under a glass atrium and boasts breathtaking views of Lake Michigan, Millennium Park, and the iconic skyline of Chicago.

For a Chicago rooftop meal with the very best views over Millenium Park and Lake Michigan, Cindy's Rooftop is undoubtedly the place to visit. Perched 13 floors up at the Chicago Athletic Association hotel, this vibrant rooftop restaurant and bar is open for both lunch, dinner and rooftop weekend brunch. With a stylish and spacious glass atrium lounge, complemented with an open-air rooftop terrace, Cindy's is at your service year round.

Imagine clinking glasses with your partner amidst a refreshing breeze while gazing at our city’s many wonders, including Millennium Park and The Bean. To top that up, Cindy's offers a selection of carefully crafted cocktails and a menu highlighting fresh, local ingredients - ideal for a sophisticated yet relaxed evening. For those who love sharing their moments, the stunning views provide the perfect backdrop for selfies.

Nestled within the historic Chicago Athletic Association Hotel, Cindy's Rooftop is a beacon of culinary and mixology excellence. This rooftop bar features a glass atrium and airy open-air sections with fantastic panoramic views of Millennium Park, the Art Institute, and the shimmering waters of Lake Michigan. This spot features a menu emphasizing fresh, seasonal ingredients in its food and drink offerings.

The Chicago Athletic Association Hotel is a landmark 1893 establishment that adds a flourish of Venetian Gothic architecture (it was modeled off the Doge of Venice’s Palace) to Michigan Ave. It’s a stone’s throw from Millennium Park, The Art Institute, and Lake Michigan so it’s virtually impossible to find a more central downtown location. Women were initially persona non grata at the CAA back in the day.

Cindy’s Restaurant brings some of the best waterfront views and an open air terrace for one of the more unique Chicago rooftop restaurants. You can dine in their gorgeous glass atrium overlooking Lake Michigan if the weather isn’t suitable for outdoor seating. Located in the Chicago Athletic Association building, you’ll find panoramic views of Millenium Park and Lake Michigan, paired with a killer menu.

It was hard to know whether to put this in restaurants or where to drink, and I accidentally came here twice in the same day—for afternoon drinks, then a late dinner with friends. And I was honestly surprised how delicious the food was…I’d expected them to phone it in and rely on the appeal of the view. Rooftops are super popular in Chicago, and Cindy’s is always one of the first that people mention.

Inspired by a Great Lakes beach house with its glowing string lights and picnic table seating, Cindy’s is the breathtaking rooftop restaurant perched atop the Chicago Athletic Association Hotel. The vaulted glass-and-steel restaurant features jaw-dropping views of Millennium Park and Lake Michigan. Choose dishes from Cindy’s menu of refined American fare, including delectable seafood options.

Cindy’s, also known as Cindy’s Rooftop, is the place to be if you want to enjoy some drinks and food along with your sunset viewing. The venue is located on the roof of the Chicago Athletic Association Hotel and offers coverage so you can enjoy your visit even during cold Illinois winters. Cindy’s isn’t exactly under the radar, however, you’ll usually encounter more locals here than tourists.

Cindy’s sits on top of the Chicago Athletic Association Hotel, offering an amazing view of Millenium Park. The menu is split between spirits, wine, beer and unique options like potions, elixirs, tisanes and mocktails. Try the full apothecary service, a $250 to $280 package that comes with 20 drinks designed to “cure your life.” No wonder Cindy’s calls its bar “the original pharmacy.

Head straight up to Cindy’s Rooftop Terrace, where the friendly bartenders will mix you a mean Old Fashioned to take out to the balcony and enjoy sweeping views of Millennium Park, the Art Institute and sparkling Lake Michigan. Be sure to drop into the Game Room on your way out to have a friendly face off over a foosball or shuffleboard table, or try your luck in the bocce bay.

If you’re looking for brunch with a view, look no further than Cindy’s. Atop the historic Chicago Athletic Association Hotel, this open-air terrace boasts some of the best views and overall atmosphere in the city. Fill up on breakfast classics such as Steak & Eggs and Buttermilk Pancakes while taking in views of Millennium Park, The Art Institute of Chicago, and Lake Michigan.

12 S Michigan Ave, Chicago, IL 60603312-792-3502 Visit Website. Located in an enclosed glass space on the roof of the Chicago Athletic Association Hotel, Cindy’s Rooftop is a stylish industrial-chic restaurant and bar. You can dine and drink from a seasonal menu of elevated comfort foods with birds-eye views of the famous Bean sculpture, Millennium Park, and Lake Michigan.

Located directly across from Millennium Park, Cindy’s Rooftop Bar has a magnificent view over Grant Park, the lakefront, and the surrounding buildings. As the sun sets, enjoying a nightcap on the balcony is an unforgettable experience as you watch the city lights come on. Book your reservations ahead because its popularity makes it a difficult destination to get in.

Topping off the historic Chicago Athletic Association at 13 stories high is the rooftop bar called Cindy's. It provides a breathtaking scene of Millennium Park, Lake Michigan, and of course the magnificent sculpture "Cloud Gate" a.k.a. "The Bean". As one of the best rooftops in the Loop, Cindy’s cocktails are balanced and aesthetically pleasing, to match the view.

Arguably, the gold standards in the Loop are the LondonHouse, where you’re treated to a vista straight down the Chicago River from 22 floors up, and Cindy’s, a farm-to-table restaurant on the 12th floor of the Chicago Athletic Association. It’s enclosed, but the glass back wall leads out to a terrace overlooking Michigan Ave., Millennium Park, and Lake Michigan.

Cindy's has been a long-time favorite of mine in Chicago, and for good reason. This public rooftop (part of Chicago Athletic Hotel) offers stunning views of Lake Michigan, Millennium Park and the Chicago Art Institute. It has floor to ceiling windows (and actually... the ceiling is glass too) so the place is bright and cheery and flooding with natural light.

Located atop the Chicago Athletic Association Hotel, Cindy’s Rooftop offers panoramic views of Millennium Park, Lake Michigan, and beyond. The open-air terrace is complemented by a glass atrium, making it a year-round destination. The menu features seasonal cocktails and a selection of sharing plates inspired by classic American comfort food.

Located atop Chicago’s Athletic Association Hotel, this spot is a must if your sport of choice is brunching. The rooftop is open year-round, with fireplaces to keep you toasty or a glass atrium if you’d rather soak in the iconic views of Millenium Park and Lake Michigan inside. Where: 12 S Michigan Ave, Chicago, IL, 60603

🍽️ New American | $$$ | Website | 📍 Google Maps | 📞 (312) 792-3502 | Neighborhood: The Loop. Cindy’s Rooftop is the place to go for rooftop dining and views. Delicious brunch, lunch, and dinner menus are available, but most people head to Cindy’s to enjoy creative cocktails, lighter fare, and the rooftop ambiance.

On the rooftop of the Athletic Association Hotel, you’ll find the cool and hip eatery called Cindy’s Rooftop. Cindy’s offers a stunning view of Millennium Park, The Art Institute of Chicago and Lake Michigan. You’ll find delicious meals and bar snacks at this restaurant and a generous list of booze-free beverages.

Cindy’s Rooftop is a must-visit rooftop restaurant in Chicago that offers a breathtaking view of Lake Michigan and Millenium Park. The place boasts a hip and eclectic atmosphere, perfect for a night out with friends. Cindy’s is where you want to be if you’re looking for an unforgettable rooftop dining experience.

If you’re looking for a Chicago restaurant with a view of Millenium Park, we highly recommend visiting Cindy’s. Your view won’t be obstructed by towering buildings in the slightest. Their balcony makes it easy to see miles of these gorgeous parks and the lake beyond while chowing down on seasonal American fare.

Cindy’s, the centerpiece of Chicago Athletic Association Hotel, offers one of the best views of Millennium Park. More of a restaurant than a bar, it’s best to make reservations in advance at this popular rooftop. Head to the hotel’s recently reopened Game Room for a round of drinks and Bacci ball after dinner.

Many restaurants with rooftop seating boast pleasant views, but Cindy's Rooftop offers one of the finest vistas in all of Chicago. The beauty of the Windy City unfolds in every direction, creating a stunning backdrop for your dining experience. As you glance at the menu, you'll discover even more to savor.

If you’re in Chicago, it’s nearing sunset, and you’re a sucker for a rooftop bar, book it to Cindy’s Rooftop. Cindy’s is located 13 stories above Millenium Park atop the Chicago Athletic Association Hotel. It has two seating areas: a glass-enclosed indoor dining area and an outdoor terrace.

Located on the 13th floor of the Chicago Athletic Association Hotel, Cindy’s Rooftop offers stunning views of Millennium Park and Lake Michigan. The restaurant serves American cuisine with a focus on seasonal ingredients. The rooftop bar is also a popular spot for cocktails and live music.

Cindy’s is our all-seasoned rooftop restaurant atop the hotel with sweeping views of Millennium Park and Lake Michigan. Providing a remarkable backdrop for Top Chef contestant Executive Chef Kaleena Bliss and her inspired menu featuring local wild and seasonal produce and fresh seafood.

You’ll get panoramic views of the lake, Millennium Park, the bean, etc. They have a well-rated restaurant and bar—an excellent spot to enjoy a cocktail on the outdoor terrace with a camera in hand. They have fire pits during the colder seasons to keep you cozy while you enjoy the view.

Cindy’s serves a platter of pancakes meant for three to four people to share. Weekend brunch (10 a.m.-3 p.m.) includes a deliciously huge plate of buttermilk pancakes with blueberries and aged maple syrup, all with the killer views that Cindy’s on Michigan Avenue is known for.

Cindy’s Rooftop certainly offers a very different view from other rooftops mentioned here. The rooftop patio opens into a view of vast green space of Grant Park blending into blues of Lake Michigan in the horizon. I love how tiny the Bean in Millenium Park looks from up here.

Cindy’s is a restaurant and open-air terrace on the roof of the Chicago Athletic Association. Situated 13 floors above the street, Cindy’s offers views of Millennium Park, Grant Park, and Lake Michigan. You can enjoy the view from Cindy’s terrace or inside the glass atrium.

This place is mostly known for it’s cocktails, but last year I went for brunch with some of my girlfriends. I’m so glad we did, because it definitely wasn’t on my radar for that at all!. I personally think this is the best brunch spot for an out of town group.

Editor's Note: Photo taken from the establishment's official social account. A post shared by Chicago Athletic Association (@chicagoathletichotel). Situated on the roof of the Chicago Athletic Association hotel is the trendy and hip rooftop bar called Cindy’s.

Cindy’s is Chicago’s other must-see rooftop bar and one of the best bars in Chicago. Set atop the Chicago Athletic Association, this rooftop bar offers incredible views of Millennium Park and the harbor. Cindy’s is definitely a bar to dress to impress.

Whether you’re eating, drinking or just enjoying the views, Cindy’s Rooftop is another Chicago staple to check out. Located in the Chicago Athletic Association Hotel the vibe here is always lively, fun and bumping!. 12 S Michigan Ave, Chicago, IL 60603

For some of the best views in the city, head up to Cindy's rooftop terrace, a restaurant and bar with commanding views across Millennium Park, the Art Institute of Chicago and Lake Michigan. STOP 5: A WATERFRONT LANDMARK

For one of the best restaurants in Chicago, you should definitely go to Cindy's Rooftop. You can get here delicious food. But besides great food, it is also a great photo spot in Chicago.

I like Cindy’s at the Chicago Athletic Association for lakefront views and a chic scene, but there’s plenty of places to choose from! There you Have it – The Perfect Chicago Itinerary!

You’ll find this rooftop bar on almost any Chicago itinerary. Cindy’s isn’t known for skyline views (although you can see skyscrapers from here). Instead, it looks over Millenium Park.

Cindy’s Bar has the perfect view of Chicago: go on the outdoor terrace to see great views of Lake Michigan and the legendary Chicago Bean.

Sip cocktails with stunning views of the city at venues like Cindy’s, LH ON 22, Raised, Cerise, VU, Upstairs at the Gwen, or J.