401 N Wabash Ave
Wrapping around the 16th floor of Trump Hotel Chicago, this seasonal sky-high lounge offers unparalleled views of Lake Michigan and the Chicago River. Drinks are exquisitely balanced, and some include flavor-infused ice cubes to make ‘em good to the last drop. Catch fireworks on Wednesdays and Saturdays all summer long.
505 N State St
When a bar’s beverage menu is equipped with a table of contents, you know it means business. Balanced and blended with top-shelf booze and predominantly local juices and herbs, each cocktail offered is a veritable work of art. Overwhelmed by all the options? The refreshing, gin-based War of the Roses and warming East of Omaha are perennial standouts.
412 N State St
With its weathered awning, unassuming Rossi’s is a breath of fresh air from the neighborhood’s swankier spots -- provided your idea of “fresh air” includes inexpensive drinks, a jukebox, and remarkably diverse clientele.