Kentucky Corpse Reviver Twinkie
at Longman & Eagle
There’s something so gleefully transgressive about pairing a retro Twinkie with the accoutrements of a Corpse Reviver cocktail and a whole lot of bourbon. Logan Square, 2657 N. Kedzie Ave., longmanandeagle.com
Tex’s Hot Cocoa
at Homestead on the Roof
The ultrarich hot chocolate hides any evidence of an alcohol burn from the crème de cassis and walnut liqueur—and it’s supertasty, too. West Town, 1924 W. Chicago Ave., homesteadontheroof.com
Prosecco Affogato
at Nico Osteria
This is literally a drink (a pour of good prosecco) with dessert in it (three scoops of even better apricot and burnt honey gelato), equal parts basic and brilliant. Gold Coast, 1015 N. Rush St., nicoosteria.com
Warm Rum Sponge Cake
at Paris Club Bistro & Bar
Not only does this cake get doused with your choice of rum, the whole shebang happens tableside. Dessert, a drink, and a show. River North, 59 W. Hubbard St., parisclubbistroandbar.com