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You live in Chicago. You don’t need to stay in a hotel here. But play in one? Sure--especially when it’s as much fun as the just-opened Chicago Athletic Association Hotel. Once a boys’ club where the likes of Marshall Field and Cyrus McCormick swung their racquets, it’s now a restored showplace filled with jaw-dropping woodwork, major art and stained glass galore. And even non-guests are welcome to come in and take a break from real life. Here’s what’s not to be missed.

CAA 1

Relax on the Roof

At Cindy’s, a restaurant with terrace on the 13th floor, snag a picnic table with a lake view and order craft cocktails created by spot’s “spirit guide,” Nandini Khaund.

CAA Game Room1
Clayton Hauck

Rule the Game Room

Pool sharks and chess whizzes, this is your new hangout. A public space filled with leisurely diversions reminiscent of the building’s 125-year history is the place to be for billiards, beer and street-food-inspired bites.

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Huge Galdones

Order the Millennium Perk

The hotel is the site of the most beautiful Shake Shack location we’ve ever seen. Go for the Chicago-centric frozen vanilla custard with Intelligentsia coffee beans, marshmallow sauce and a crumbled Glazed & Infused old-fashioned doughnut.

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Score New Shades

The Chicago retailers behind the chic “urban general store” Space 519 are opening a new shop, Madison Hall, on the ground level of the hotel. If you find yourself downtown and besieged by a glare, consider it an excuse to pop in for a pair of Illesteva shades.

CAA McGee
Clayton Hauck

Drink in Chicago’s Tiniest Bar

You know how the epically bearded Paul McGee is always the mixologist at the coolest new bar in town? Find him here slinging rare whiskies in the eight-seat Milk Room (it’s a Prohibition reference, people). McGee also created cocktails for the Cherry Circle Room, the hotel's full-service restaurant where the food and drinks are full of historic references dating back to CAA's original heyday. 

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Catch Some Zzz’s

Like the rest of the place, the rooms are gorgeous. A staycation in a suite overlooking Millennium Park--complete with custom Egyptian cotton sheets on the king bed and a mini bar stocked with locally made goodies? Don’t mind if we do.

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