simon's tavern bar chicago

Simon’s Tavern

The neighborhood’s Swedish history lives on in this worn-and-warm tavern, which dedicates one whole wall to a deer-hunting mural featuring regulars from years past. There are also goblets of seasonal…

delilah's bar chicago


Any lived-in, urban dive that pays homage to Joe Strummer, pinball and whiskey in equal measure, could be a potential classic. Delilah’s—dark, friendly and loud—is. It boasts more than 600…

Cole's Chicago dive bar


An offbeat, welcoming joint surrounded by craft breweries and fancy cocktail houses, Cole’s is a throwback that hosts revolving art exhibits, variety shows, live bands and a mentalist. It also…

carol's bar chicago

Carol’s Pub

The clientele at this rowdy 4 a.m. country bar is unlike any other in Chicago. Old winos, yuppies, cougars, college kids and urban hillbillies all come together to dance and…

The Matchbox Chicago dive bar

The Matchbox

The Matchbox is a Chicago institution that dates to the 1990s, well before mustachioed mixologists entered the scene. This is the kind of place where classic Collinses are still mixed…

Big Star Chicago day drinking

Big Star

A little slice of Austin in Wicker Park, Big Star is about as country as Chicago gets—which is to say, not very. Vintage neon and a vinyl soundtrack are the…