When President Barack Obama’s 2012 reelection win was announced on television, the patrons at Simon’s paused just long enough to clap and exchange pleasantries with one another. Then it was back to business as usual: middle-aged couples wrapping up their date night; young theater kids making merry with slightly more energy than necessary; the regulars holding the bar up. In short, Simon’s is unflappable. It manages the same energy whether packed with holiday revelers looking for their glögg and ginger cookies or hosting a few neighborhood denizens quietly nursing their weeknight beers. One of the oldest bars in the city, it’s potentially haunted, but these might be the mellowest ghosts in Chicago — perhaps their only unfinished business is getting to the bottom of their glasses.
Address: 5210 N. Clark St.
Year opened: 1932
Drink of choice: Hot glögg in the winter, glögg slushies in the summer, or a beer and a shot year-round
Clientele: Anyone who enjoys leaning — on the bar, on the jukebox, or against the wall waiting for the bathroom
Song you might hear: The staff regularly switches the jukebox CDs, which can range from the Cocteau Twins to Lana Del Rey