Chicago Athletic Association Hotel
12 S. Michigan Ave.
For those liquor connoisseurs able to pony up for a $50 ticket, this intimate bar is required boozing. Cocktail visionary Paul McGee—see also Lost Lake (No. 3)—enhances classic drinks with ultrarare (and ultrapricey) vintage spirits.
Who’s there:High rollers and rare-booze nerds
What to order:Armillita Chico ($32): tequila, mezcal, pomegranate, lime, Angostura bitters