Old Town Ale House Chicago

Walking down the bustling streets of Old Town, you're likely to pass their ratty, algae-green awning without a second glance—choose to take a peak and stop inside this dive bar, though, and you’ll be taking a seat among some of Chicago’s richest, most historic spots in the city.

Spend enough time there and you’ll become part of the walls… literally. One of the bar’s most notable features is the portraits of historic bar dwellers hanging throughout almost every inch of the interior. Located directly across the street from Second City, it’s no surprise that some of comedy’s most famed faces reign high above on the walls, including Tina Fey and Michael Shannon. These odes to Second City greats aren’t the only comedic references amongst the paintings—peruse around and you’ll see a naked Sarah Palin strapped with a rifle, international leaders in compromising positions, and a whole lot more.

My advice to first-timers? Grab a seat at the bar, order the negroni on ice, queue up an instrumental melody on the cash-only jukebox, settle in, and buckle up for a visual ride through the bar’s eclectic, famed story.

Whether you stop by for the notoriety or spend an entire day pleading your case to get your portrait painted, Old Town Ale House is one of my favorite spots to enmesh myself in the history, art, and unique company found in Chicago.