Matt Kirouac

Long gone are the days when hotel dining meant room service or cliched banquet fare. The new guard of hotels taking shape in Chicago, in fact, are home base to some of the best new dining and drinking destinations in town.

The finest example of Chicago's fresh new hotel dining scene is the Chicago Athletic Association Hotel, a property that just opened across the street from Millennium Park. This renovated and reimagined property, a modernization of a long dormant hotel that originally opened in the late 1800s, is a beautiful homage to Americana and old-school Chicago. Leading the charge on that modernization is a collection of some of the greatest dining and drinking destinations downtown. On the ground floor is Shake Shack (above), the second Chicago outpost of the feverishly popular burger chain. Across the lobby will soon be a chocolate wonderland in the form of a new Vosges store.


Matt Kirouac

Ascend the glam staircase to the second floor and immerse yourself in a whole world of gustatory delights. Here, Land & Sea Dept. takes the lead, a venerable local restaurant group responsible for such hot spots as Longman & Eagle and Lost Lake. The Drawing Room is a splendid lounge-y area serving coffee and pastries during the day, booze and snacks by night. Down the corridor is Game Room (above), an adult playground of billiards, bocce and table games adjoined by classic American cocktails and a dreamy menu of contemporary comfort foods, like fried pickle pops, boozy freeze pops, and lime-splashed popcorn. The man behind the cocktails here is the one and only Paul McGee. The world renowned bartender flexes his dexterous mixology muscles by curating classics for Game Room and upscale libations with rare spirits at micro-bar Milk Room.

Meander past Game Room and you'll find yourself in Cherry Circle Room, a dimly lit throwback dining room reminiscent of a scene from Mad Men. The restaurant, presided over by Chef Peter Coenen, is a renaissance for the original Cherry Circle Room, which first existed when the hotel opened more than a century ago.

In case all of that isn't enough to dazzle you, the Chicago Athletic Association is also home to one of the chicest new rooftop restaurants in town. Cindy's can be accessed on the 13th floor, where contemporary cocktails contain ingredients like cardamom and pistachio milk. Christian Ragano oversees a menu of seasonal share plates, and an enormous balcony ledge provides a stunning vista of Lake Michigan, Millennium Park and Grant Park.


Matt Kirouac

The Chicago Athletic Association is ravishing enough by itself, let alone the other hotels and on-site restaurants popping up around the city. The new Loews Hotel pays homage to Argentine steakhouse traditions with Rural Society, a restaurant manned by Iron Chef Jose Garces and Chef Cory Morris. Freehand Chicago is a new outpost of Miami's beloved Freehand hostel and hotel, complete with a location of Miami's world famous Broken Shaker cocktail bar (Cocoa Puff-infused Old Fashioneds included).

And billionaire Sir Richard Branson made his mark in a big way with the Loop's new Virgin Hotel, the first and currently only Virgin Hotel in the world. Here, Chef Rick Gresh runs a handful of dining operations, including Miss Ricky's diner (get the Death by Chocolate cake, complete with an edible, caramel-filled "knife"), The Commons Club bar and restaurant, and Cerise, a sleek rooftop lounge on the 26th floor with quasi-Japanese izakaya fare.

Photos: Shake Shack, Game Room, Freehand Chicago