Margie's Candies, 1960 N Western Ave; 773.384.1035
An old-timey ice cream parlor that’s right near the Gorilla Tango, so grab sweets here first, and then catch a burlesque show matinee. Actually that might be awkward. Just stick to the nostalgic candies and sundaes.
Palm Court at the Drake, 140 E Walton Pl; 312.787.2200
Take tea and finger sandwiches as you listen to soothing sounds of live harp music, interrupted only by the sounds of you scarfing way too many finger sandwiches. If your grandparents happen to be British this becomes an even stronger move.
THE GUEST: YOUR SISTER AND HER THREE-YEAR-OLD KID
It's rough dealing with toddlers who are too young to be good at video games and too old to be entertained by a mobile. Do your sister a solid and keep the kid occupied, proving that you're the cool uncle and not the creepy uncle.
Candyality, 3425 N Southport Ave; 773.472.7800
Let ’em ride that sugar high as you indulge in candies you didn't even think they made anymore (Zots?!), because you don't have to take care of them later when things come crashing down (note: does not work for diabetics).