Sixteen was an American restaurant on the sixteenth floor of the Trump International Hotel and Tower in the Near North Side community area of Chicago.

The eastward view included Lake Michigan, Chicago River, and the Wrigley Building clock tower.

Sixteen was designed by Joe Valerio, whose previous credits included the Garmin flagship store on the Magnificent Mile.

[4] Valerio's design had to work within spatial constraints determined by the tower's architects, Skidmore, Owings & Merrill, leaving him to deal with complications stemming from a variety of column shapes — some square, some round, and others rectangular.

Kamin regarded these views to be "more intimate" than the panoramic ones of the Signature Room, a restaurant near the top of the 100-story John Hancock Center.

After a five-year tenure, he moved to Dublin, Ireland, where he worked as a sous chef at the Michelin two star-rated Thornton's Restaurant.

During his time abroad, Lents staged in acclaimed kitchens, including the Michelin three star-rated Waterside Inn in Bray and Le Manoir Aux Quatres Saisons in Great Milton.

"[18] According to a 2008 review from Time Out Chicago, the restaurant is more a place to impress clients and dates, rather than a top–notch dining experience with top-notch cuisine, due to its association with Donald Trump and its views.

[10] The magazine's annual Eating & Drinking guide describes the dining room as stately and impressive, the staff as attentive and professional, and the food as "well-presented.

[22] When Chicago became one of three American Michelin Guide star-rated cities in November 2010, Sixteen was one of 23 restaurants to receive at least one star for 2011.

[3] The Terrace, opened on June 25, 2009,[34] has views of the Chicago River and Lake Michigan as well as Navy Pier's seasonal Wednesday and Saturday evening fireworks and was designed for al fresco dining.

[35] It is located adjacent to Sixteen on the first setback of the tower,[4] and it was part of a larger 2009 movement to supply al fresco dining options to the Chicago marketplace.

[37] Although it offered a menu of appetizers and entrees, it was said to focus on serving drinks,[35] and Time Out Chicago describes it as a posh playground for consuming cocktails.

[40] In 2008, one member of the WMAQ-TV Street Team commended it for its signature cocktails and sushi,[45] while another preferred to highlight its stainless steel swizzle sticks.