Whether you prefer yours shaken or stirred, there's no shortage of cocktail spots to provide your fancy-drink fix.
First, order up at The Barrelhouse Flat (2624 N. Lincoln Ave. 773-857-0421), a sexy two-floor lounge where progressive bartenders push the envelope when it comes to fun ingredients while still respecting the classics.
Next, head to the historic Pump Room (1301 N. State Parkway 312-229-6740) inside Gold Coast hotel Public and grab a seat at the sleek white bar, which still preserves all the old-Hollywood glamour of the '30s and '40s.
Scoot over to the Raffaello Hotel and take the narrow elevator to 18th-floor spot Drumbar (201 E. Delaware Place 312-933-4805) for cocktails, a rooftop lounge and fantastic views.
Still standing? Good, because it's time to take your pick of both classic and modern creations from the bar talent at subterranean lounge The Drawing Room (937 N. Rush St. 312-266-2694).
Wind down with a nightcap at Bernard's Bar (11 E. Walton St. 312-646-1400), an intimate lounge tucked inside the swank Waldorf Astoria hotel.