Sixteen has transformed itself under chef Thomas Lents—with creative themed tasting menus like Chicago History, more approachable service and two Michelin stars, the restaurant is solidly in the top tier of fine dining restaurants in Chicago. While the tasting menu is firmly in "splurge" category (dinner for two with wine pairings is around $1,000), the patio offers an even better view of the Wrigley Building and Tribune Tower, as well as less expensive food.
Trump Hotel, 401 N Wabash Ave
|Cross street:||at Kinzie St|
|Opening hours:||Breakfast, brunch (Sun), lunch, dinner|
|Transport:||El stop: Red to Grand. Bus: 29, 36, 65.|