14. Rebar at the Trump Chicago

CITY: Chicago
ADDRESS: 401 North Wabash Ave.
WEBSITE: trumpchicagohotel.com

In a Trump establishment, you should know walking in that cocktails are gonne be expensive, but if you nab a seat by the window, the views of the Chicago River and Michigan Avenue Bridge will take the ease off the price of your $17 cocktail. Rebar is arranged so you can get comfortable, with stuffed chairs replacing bar seating around dimly lit low tables, condoning a night of conversation and exuberant spending, just the way the Donald would have it.