Coolest Bars to Catch Live Music in Chicago

Whether your poison of choice veers more towards local brewski or stiff cocktail, there’s no shortage of Chicago bars to sidle up to when it’s time to unwind. If it’s drinks and live music you’re after, however, we’ve got a handful of venues worth moving to the top of your list. For quality beats and...

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Whether your poison of choice veers more towards local brewski or stiff cocktail, there’s no shortage of Chicago bars to sidle up to when it’s time to unwind. If it’s drinks and live music you’re after, however, we’ve got a handful of venues worth moving to the top of your list.

For quality beats and beverages, here are the coolest bars in Chicago to catch live music.

Redhead Piano Bar

The iconic Redhead Piano Bar has been on the Chicago scene since the early 90s, standing the test of time with talent that just won’t quit and a recently renovated, sleek interior. Everything from Top 40s to Broadway show tunes fill the request jar at this piano bar until the wee hours of the morning every night of the week (4 a.m. Su-F, 5 a.m. Sat).

And while you’re there, don’t forget to cap off your night with a smoke in their newly opened “Cigar Den.” With over 150 cigars to choose from their walk-in humidor, you’ll have no problem finding something suited for your palate.

Howl at the Moon

We’ve got two words: dueling pianos.

This hyped party bar in Chicago’s River North neighborhood is not for the faint of heart or voice. Taking requests for everything from pop to classic rock to hip hop, the performers at Howl at the Moon are both musicians and entertainers. Plan a group night out full of singing, dancing, and sipping from an 86 ounce bucket o’ booze.

Hard Rock Cafe

Rock history meets live bands at this music mecca. From an amazing collection of memorabilia from the likes of Prince, Billy Joel, and Buddy Guy to delicious dining, a trip to Hard Rock Cafe gives you a true music experience you don’t want to miss. Enjoy live music from guest artists, plus weekly live band karaoke if you’re feeling inspired to channel your inner Mick Jagger.

Andy’s Jazz Club

Get your jazz fix seven nights a week at Andy’s Jazz Club. This intimate lounge sits two blocks west of the Magnificent Mile and has kept patrons coming back with lively entertainment since 1951.

Aragon Ballroom

From Buddy Guy to Styx, Fall Out Boy to Lupe Fiasco — if the walls at the Aragon Ballroom could talk, they’d most certainly sing. You’ll find this concert hot spot right off the Lawrence Red Line stop with a one-of-a-kind, starry night ceiling in the main hall.

Empty Bottle

When we say, “cheap”, you say, “drinks!” While a bit off the beaten path in Chicago’s West Town/Ukranian Village, The Empty Bottle is popular for their indie and alternative lineups, and Free Mondays!

Green Mill

Go to the Green Mill for the jazz, stay for the historic ambiance. Operating since 1907, you can find Al Capone’s favorite booth from Prohibition days situated west of the short end of the bar.

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Craft cocktails and an alluring speakeasy vibe pair all too well with this River North establishment’s unique calendar of live music, burlesque, and circus-inspired shows.

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