You walk into the lobby of the Chicago Athletic Association, and it feels like you've accidentally stepped into a 19th-century secret society. Dark wood. Gothic arches. Stained glass. It’s heavy. But then you cram into that express elevator, the doors slide open on the 13th floor, and everything changes. The air gets lighter. The view hits you like a physical weight. Honestly, the chicago athletic association rooftop—specifically known as Cindy’s—is one of those rare places that actually lives up to the Instagram filters.
It's a glass house in the sky.
Most people come here for the view of Millennium Park, which, yeah, is spectacular. You're looking directly down at the "Bean" (Cloud Gate) and the Pritzker Pavilion. But there’s a nuance to this place that people miss if they’re just there to snap a photo and leave. It’s a transition from the "Old Boys Club" vibe of the lower floors—originally a private men's club founded in 1890—to a bright, communal space that feels remarkably inclusive for a luxury hotel bar.
What Most People Get Wrong About the Chicago Athletic Association Rooftop
There is a common misconception that Cindy’s is just a seasonal spot. People think, "Oh, it's Chicago, it's freezing, I can’t go to a rooftop in January." That's wrong. Because the space is designed like a conservatory, it’s actually better when it’s snowing. You’re sitting under a massive steel and glass canopy, warm as a toast, while Lake Michigan looks like a frozen wasteland just a few blocks away.
The terrace is the only part that's truly "outside."
Even then, they’ve got those massive fire pits. People huddle around them with spiked hot chocolate. It’s a vibe.
Another thing? The food. A lot of rooftops in the Loop or River North treat food as an afterthought—greasy sliders or overpriced truffle fries just to keep you drinking. Cindy’s does family-style dining. We’re talking massive platters of Lake Superior Whitefish or roasted chicken that are meant to be passed around. It’s not a "snack while you look at the view" place; it’s a "sit down and lose two hours of your life to a meal" place.
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The Design Philosophy of Roman and Williams
The firm behind the restoration, Roman and Williams, did something really clever here. They didn't try to make it look brand new. They leaned into the "faded glory" aesthetic. You’ll notice the mismatched textures and the way the light hits the apothecary-style bar. It feels like it’s been there forever, even though the hotel only opened in its current form in 2015.
Before the 2015 reopening, this building was basically a time capsule. The Chicago Athletic Association club had closed in 2007, and for years, it just sat there. When you stand on the chicago athletic association rooftop now, you’re standing on top of a building that once hosted the city’s elite athletes and power brokers. The ghosts of old Chicago are in the walls, but the rooftop is where the city breathes.
The Logistics of Actually Getting a Table
Let’s be real: getting in can be a pain.
If you show up at 7:00 PM on a Friday without a plan, you’re going to be standing in a line in the lobby next to a velvet rope feeling like a tourist. Don’t do that.
- Reservations are for dining. If you want a seat and a full meal, book weeks out. Especially in the summer.
- The "Bar" is first-come, first-served. This includes the terrace.
- Go for lunch. This is the pro move. The light is better for photos, the crowds are thinner, and the "Great Lakes" fish sandwich is actually one of the best things on the menu.
- The side door. Sometimes, if the main elevator line is long, you can wander through the second-floor "Game Room" (which you should see anyway) and find the back elevators. It doesn't always work, but when it does, you feel like a genius.
The drink menu changes seasonally, but they always have "Spirit-Free" options that aren't just sugary juice. They take their mocktails as seriously as their Old Fashioneds. It’s refreshing. Chicago has a massive drinking culture, but Cindy’s manages to feel sophisticated without being exclusionary to the sober-curious crowd.
Why the View is Different Here
You aren't as high up as you are at the Willis Tower or the John Hancock. And that’s a good thing.
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When you’re on the 100th floor of a skyscraper, the cars look like ants and everything is abstract. On the 13th floor of the Chicago Athletic Association, you’re at "human scale." You can hear the music from the Jay Pritzker Pavilion if there’s a concert going on. You can see the expressions on the faces of people walking through Millennium Park. You feel connected to the heartbeat of the city, not hovering above it like a gargoyle.
Beyond the Rooftop: The Rest of the Building
You can't talk about the rooftop without mentioning what’s underneath it. The building is a playground.
After your drink, you should definitely head down to the second floor. The Game Room has bocce ball, billiards, and shuffleboard. It’s loud, it’s fun, and it smells like expensive leather and popcorn. If you need something quieter, the Drawing Room is basically a massive library with three ginormous fireplaces. It’s the best place in the city to answer emails or read a book while pretending you’re a 1920s millionaire.
Then there’s Cherry Circle Room.
It’s tucked away, dark, and intimate. If the rooftop is the "wow" factor, Cherry Circle Room is the "soul." It won a James Beard Award for its design, and the leather booths make you feel like you're about to plot a heist or a merger.
What to Order (Real Talk)
Don't just get a gin and tonic.
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The cocktails at Cindy’s are curated by people who clearly care about bitters and botanicals. Look for anything involving seasonal shrubs or house-made syrups. For food, the "Cast Iron Cornbread" is basically mandatory. It comes with honey butter that I’m pretty sure is addictive.
Is it expensive? Yeah. You’re paying a "view tax." A cocktail will run you $18 to $22. A large format dinner platter can easily hit $80. But you aren't just paying for the liquid in the glass; you're paying for the fact that you’re sitting in one of the most iconic architectural triumphs in the Midwest.
Practical Insights for Your Visit
To make the most of the chicago athletic association rooftop, you have to time it right. The transition from "Golden Hour" to twilight is the sweet spot. The way the sun reflects off the glass of the surrounding skyscrapers—specifically the Aqua Tower and the St. Regis—is a light show that no money can buy.
- Check the weather. If it’s extremely windy, the terrace might be closed. The wind coming off Lake Michigan at that height is no joke.
- Dress code. It’s "Chicago Casual." You’ll see people in suits next to people in nice sneakers and jeans. Just don't look like you just rolled out of bed and you'll be fine.
- The Fire Pits. If you're there in winter, snag a spot by the fire early. Once people sit down, they don't move for an hour.
- The Secret View. Walk all the way to the ends of the terrace, not just the middle. The angles of the Art Institute from the south end are incredible.
The Chicago Athletic Association isn't just a hotel; it’s a gift to the public. For decades, this building was closed off to everyone but the wealthy members. Now, anyone can walk in, head to the roof, and claim a piece of that view. That’s the real magic of the place. It’s a democratized luxury.
Next Steps for Your Chicago Trip
If you’re planning to visit, your first move should be checking the Cindy's Rooftop website for any private event closures—they happen often because it's a prime wedding spot. Once you've confirmed they're open, aim for a late afternoon arrival. Start with a walk through the Art Institute of Chicago right across the street, then cross Michigan Avenue and head straight up to the 13th floor. Order the seasonal sangria or a local craft brew, find a spot on the railing, and just watch the shadows stretch across the park. After the sun goes down, head to the second-floor Game Room for a round of shuffleboard to round out the night. This isn't just a tourist stop; it's the definitive Chicago experience.