Old Town Ale House

"Character is not something Old Town Ale House is short on. At its core, Old Town Ale House is a funky dive bar and historic hangout full of locals and comedians because of its location near Second City. The longtime owner also treats it as his own art studio, which includes pictures of Vladimir Putin as a ballerina and Kim Jong Un and Dennis Rodman together on the wall. It’s the total opposite of everything else you’ll find near it on Wells St., which makes Old Town Ale House the perfect escape for a lowkey couple of drinks." - josh barnett, sam faye, john ringor

"With walls completely covered in portraits of regulars and celebrities, plus some less-than-flattering paintings of political figures in less-than-savory situations, there truly is no bar like Old Town Ale House. Going strong since 1958, this cash-only institution attracts every form of Chicagoan—people in the neighborhood, students, resident funny people from Second City across the street, and even Michael Shannon. If you’re an expat looking to inherit some Chicago pride from longtime regulars, or are a born-and-raised city-dweller simply seeking cold beer and maybe a chance encounter with an icon, this is the place to be. Possible Conversation Topics: How many celebrities you can recognize from the portraits on the wall, highlights from the cash-only jukebox, favorite Michael Shannon movie (Kangaroo Jack is valid)." - john ringor

"The longstanding central heart beat of the Old Town neighborhood is most definitely the Old Town Ale House. Open since 1958, the Ale House is home to regulars and new faces alike, and its location directly across the street from The Second City makes it a watering hole for local comedians. Owner Bruce Elliot is famous for the politically charged, and quite raunchy, paintings he creates that line the walls of the Ale House. The smell of cheap beer and the sounds of the vintage jukebox make the Old Town Ale House truly special. If you're looking to grab a beer, listen to some Muddy Waters, and experience a true Chicago landmark then the Old Town Ale House is for you." - Kake

"The Old Town Ale House is a slice of Chicago history. They don’t make dives like this anymore. A staple in Old Town since the 1950s since the neighborhood was a bohemian hangout, the bar features portraits of a few famous folks, including some regulars, all painted by owner Bruce Elliot, and a lending library for bookworms." - Eater Staff

"This late-night den was a favorite of the late Anthony Bourdain who filmed several TV segments here as it’s the antithesis of many of the yuppie Old Town bars around the corner on Wells. The dive sports inappropriate paintings of Chicago history, including depictions of formerly incarcerated ex-Gov. Rod Blagojevich and is a destination for many, drawing a diverse group of patrons from all walks of life. Keep the drink orders simple." - Ashok Selvam, Naomi Waxman