The Loop • $ $ $ $
12 S Michigan Ave Chicago, IL 60603
Nineteenth-century grandeur meets twenty-first century schwank at the Chicago Athletic Association. This historic private club in the heart of the loop has been reimagined as a multi-storied palace of chic consisting of five restaurants, four bars, and an entire hotel. Honestly, this is the only place that would make us stay in the loop after 7p.m.
While each bar and restaurant within the Chicago Athletic Association has a unique vibe of its own, what permeates each equally trendy space is the jaw-dropping 19th century detailing from the spot’s club days. From vaulted ceilings and huge fireplaces to old works of art, the Chicago Athletic Association is truly a sight to behold. Of course, the older days weren’t known for its LED lighting, so don’t be surprised if some parts of the Association are a bit on the dark side.
The Cherry Circle Room, the Association’s premier bar and restaurant. You can expect a wait, so squeeze in a game of bocce in the Game Room before your table’s ready. Equally popular for the cocktail-centric crowd is Cindy’s, the CAA’s airy and bright rooftop bar and restaurant, which offers creative libations, a full menu, and views overlooking all of Millenium Park.
From the Shake Shack hamburgers on the ground floor to the rooftop views of Lake Michigan, The Chicago Athletic Association dazzles from top to bottom. The Milk Room’s craft cocktail are made with a variety of rare vintage spirits that will wow even the most discerning of boozehounds, while the Game Room feels like what would happen if Hogwarts had a sports bar. Every inch of this place is amazing, but what gets us the most is their rooftop restaurant, Cindy’s—the menu’s so good you’ll be grateful for the extra mouth room the view gave you after your jaw hits the floor.
4.0 / 5