The dining room of Stephen Gillanders’s restaurant has never felt particularly stuffy, but perching yourself atop one of the velvet stools in the bar delivers an additional dose of conviviality: The bartenders are quick with both the one-liners and your order of lobster dumplings, and you’ll have an easier time buttonholing sommelier Charles Ford for intel on the wine list’s hidden gems. 1239 W. 18th St., Pilsen, skyrestaurantchicago.com