A Giant’s Guide to Music in Chicago

Chicago—home of da Bulls, da Bears, and da Cubs. The place where Catherine Zeta Jones and Renee Zeilweger once shot their husbands and then did a song and dance to celebrate… But that was a different time and a different place.

All really dumb musical theatre jokes aside, the Windy City is home to some of the best food, booze, and blues music you can find this side of the Mason-Dixon Line. In this post I’ll be discussing three of the best music bars in Chi-town.

Kingston Mines (2548 N Halsted St.)

Perhaps the most famous of all the dive blues bars in all Chicago, this unique venue has live music from 8 PM till the crack of dawn (4 AM!!!) every night. Unlike most music venues which have 1 stage for live music, Kingston Mines has two stages which allows one band to finish and another one to keep the music going all night long without stopping.

Jess and I went on a Tuesday night after going to see da Cubs (dat’s right, da Cubs) play. Cover was a reasonable $15, and it was worth every dollar. There was a sizeable crowd for a work night, but I’m pretty sure none of us had to work the next morning. One Chicago’s finest musicians was on stage—Joanna Connor. The woman can absolutely shred on the guitar like few I’ve head. While listening to those sultry sounds of the blues, we kicked back a few cinnamon snake bites—a cocktail which I can’t really tell you what’s in it, but it’ll get the job done.

Once the first act got done, it was time to change locations—to the other room. Up next was another outstanding blues group (Mike Wheeler Band) which mixed in some of the hits of Motown. A few snake bites (and beers) later, and we were both thoroughly liquored up and enjoying ourselves immensely. Staying up till the crack of dawn never felt so easy.

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Mom’s Place (650 N Dearborn St.)

The North Side local dive, Mom’s Place, is another must go-to for anyone who enjoys good beer, good vibes, and some good music. We went there on a Friday night, when the live band was playing all the hits from Motown, classic rock, and even pop. However, we didn’t first stop in for the band, but instead headed to the back for some karaoke… Oh, I didn’t mention that in one room there is a live band and in the next is a karaoke bar.

All in all, this pub has a cozy feel and decent atmosphere with an entertaining music scene. If you are feeling like you want to hear “Don’t Stop Believing” by Journey, but you can’t decide if you want to hear someone sing it or hear yourself ruin it, then this is the bar for you.

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Blue Chicago (536 N Clark St)

My personal favourite venue, though, was Blue Chicago. This hole-in-the-wall blues bar has a cozy feel and atmosphere that is hard to be. If I was gonna order 1 bourbon, 1 scotch, and 1 beer then this would be the place I’d do it—in fact a 70 year old man did it right next to me. Located a 15 minute walk from our hotel in the Near North Side neighborhood, this place has a blues scene that you just have to experience.

Now the bouncer ($10 cover), I hear, is a local blues legend. But don’t try to talk to him because he’s not fucking interested. Now we didn’t try this personally, but we definitely saw a few people trying to chat him up and getting flat out denied….of course, the rumor is if you slip him a $20 he’ll take a picture with you. Regardless of the less-than-warm reception you’ll get at the door, the wait staff is friendly and the bartender will pour you some good strong drinks too. Just don’t expect to find any upscale cocktails on special. Here you’ll be enjoying $5 Bud Lights or $5 whiskey sours with strongly poured well whiskey.

But the blues here! You’ll be swinging your head and smacking your knee while the notes tickle your ear. It’s a small venue, so they feature 2 bands each night with 3 sets in total. Each band offers a different flare—Motown, classic blues, or maybe blues rock. If you love live blues music, this is a must see in Chicago.

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