The Best Bars with Live Music in Chicago

The Empty Bottle has been a staple of Ukrainian Village since 1992. Proudly described by the bar itself as a “hole,” this indie-rock dive bar has built its reputation on cheap drinks, a lack of pretension, a dedicated crowd and, of course, live music. Over the years it has hosted a ridiculous number of bands that have gone on to become huge, like the Yeah Yeah Yeahs, The Flaming Lips, Vampire Weekend, and The Strokes.

Alongside purportedly being the oldest music venue in Wicker Park having opened in 1954, Phyllis’ Musical Inn is most famous for putting on local bands. Most nights have free live music, with a cover at weekends depending on the bill. If hearing young Chicago bands while enjoying cheap drinks in a no frills setting is for you, make Phyllis’ your next night out.

Talking of longstanding dive bars, The Hideout takes longstanding to the next level, dating all the way back to its legal opening in 1934 and beyond. This “regular bar for irregular folks” is to be found in a 19th century house between factories and empty lots along the North Branch of the Chicago River. Chicago legends Billy Corgan and Wilco have performed low-key and unusual sets here over the years, alongside a wide array of genres and styles.

Another bar that goes back a long way is The California Clipper in Humboldt Park. Alongside the classy, retro interior and extensive range of classic cocktails, there is live music most nights, with the cover charge typically $5. A range of acclaimed acts play the Clipper, spanning soul, jazz, blues and more. Whether you settle into a booth bathed in moody red light or get up and dance with the regulars, it’s all good.

Though it’s more a restaurant than a bar, live music seven nights a week and some of the city’s best barbecue make Smoke Daddy a must-visit on this list. Blues, jazz, alt-rock, folk, country, and bluegrass are just some of the genres you can expect to hear every night of the week and on Sunday afternoons.

Pizza, craft beer, and live music? Under one roof?! If you think you can handle such a perfect combination, Wicker Park’s Piece Brewery and Pizzeria is the place, with regular live music to complement the thin crust pizza, and beers like the “Top Heavy Hefeweizen” and “Dysfunctionale.” Live band karaoke is also held every Saturday at 11pm. Expect a queue.