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Visiting downtown Chicago this year? In addition to Loop landmarks such as the Bean and the Art Institute, make a point of stopping at one of Michigan Avenue’s newest landmarks.

The Chicago Athletic Association Hotel has found new life in the heart of the city.  Founded in 1893 as a private, men’s-only club, it thrived for over 100 years before closing in 2005.

Just over a year ago, it found new life. It was renovated, restored and reopened with public spaces and private hotel rooms. It’s been such a hit with locals and tourists alike that Eater Chicago proclaimed it “the most ambitious — and influential — hospitality projects downtown Chicago has seen in years.”

From those seeking a quick bite on the ground floor, to those who opting to savor a specialty cocktail on the trendy roof bar, the CAA now welcomes anyone to see its new look, and get a glimpse of its history.

Whether you’re a guest, or just stopping by, here are a few places to enjoy the luxury of the Chicago Athletic Association Hotel.


Cindy’s is the hotel’s crown jewel of sorts. The rooftop restaurant/ bar offers craft cocktails, sharable plates and is a great place for sight-seeing. Its outdoor patio overlooks the Art Institute of Chicago, Millennium Park and Lake Michigan. Stop by on a Wednesday or Saturday night during the summer to get one of the city’s best views of fireworks at Navy Pier.

Cherry Circle Room

The Cherry Circle Room is a reinvented, iconic, fine-dining restaurant tucked deep inside the hotel’s second floor. It has been restored and renovated but gives a nod to the hotel’s history by basing its offerings onoriginal menus from the 1890. Developed by Land & Sea Dept. – the group responsible for foodie hot spots such as Longman & Eagle and Lost Lake – the room has original features, along with a few touchups.

Game Room

True to its name, the Game Room hosts plenty of pastimes. The dim-it, wood-paneled room – which offers a bar and its own food menu – keeps patrons busy with activities such as a built-in bocce bay, pool tables, shuffleboard, and chess and checkers tables.

Milk Room

This one-time speakeasy evokes the prohibition era with rare, whiskey-based cocktails and spirits. Of all the places to eat and drink in the hotel, this one is the smallest, with seating for just eight. Located near the Game Room, Time Out Chicago likens the Milk Room to “drinking in an old monastery.” There are candles lining the walls, stained glass and iron light fixtures hanging above.

Shake Shack

This New York import may offer burgers, fries and of course, shakes, but it’s far from a typical fast-food joint. Located on the hotel’s ground floor, the sandwich shop comes with a view of the lobby’s sky-high ceilings, stained glass and a marble staircase.