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Tom, Dick & Harry’s Guide to Chicago (and a few nearby) Music Festivals

By: Steve H.

Sweet sweet summer has arrived in Chicago. If only there were countless ways to soak up the short-lived weather, imbibe to the nth degree and listen to live tunes…

Oh, right! We live in one of the best music festival cities in the world. In honor, here are some recommendations from a former college DJ and our resident “oh you’ve never heard of them?” guy.


Spring Awakening

When: June 12-14

Where: Soldier Field

Who: While I’m not the biggest EDM-head I can imagine screaming and dancing to Jack Ü (The DJ duo of Skrillex and Diplo) in the middle of an NFL stadium will be nuts in all the right ways. Consider it your cheap alternative to being at a Super Bowl halftime show.


When: June 13-September 12

Where: Highland Park, Ravina Pavilion

Who: Ravinia runs all summer, so pick and choose. If I were going to trek out to the burbs on the Metra, I’d go see Lady Gaga and Tony Bennett. While I don’t recommend the show on musical merit alone, the fact that these two are touring the world together is too weird to miss. If you’d prefer music over spectacle, find tickets for the sold out Aretha Franklin show on July 11th.

Chicago Blues Festival

When: June 12-14

Where: Grant Park

Who: Chicago is the birthplace of electric Blues music, so be a damn Chicagoan and enjoy. This is my dad’s favorite festival so I’d be a disgrace to the family if I didn’t recommend multiple acts. Namely: Buddy Guy, Eddy Clearwater and Clarence Carter. And be sure to pay your respects to the late B.B. King by pouring out some brew on the Grant Park grass. 

Windy City LakeShake

When: June 19-21

Where: First Merit Pavilion at Northerly Island, Chicago

Who: If somehow you get roped (cowboy pun) into going to this thing, I know from a few first-hand experiences that Florida Georgia Line pairs well with Pabst Blue Ribbon.


When: June 24-28, June 30-July 6

Where: Henry Maier Festival Park, Milwaukee, WI

Who: “The World’s Largest Music Festival” has a lineup to match. But a shortlist includes Kendrick Lamar (with a likely cameo from Schoolboy Q), Stevie Wonder, Shakey Graves, Sylvan Esso, Charles Bradley and Milwaukee hometown-hero WebsterX.

Taste of Chicago

When: July 8-12

Where: Grant Park

Who: Erykah Badu. All hail queen Erykah. Also chill the heck out to Spoon.

Mamby on the Beach

When: July 11-12

Where: Oakwood Beach

Who: This is the first-annual Mamby so no one really knows how it’ll go. That said, listening to Passion Pit on a beach can’t go wrong. 


When: July 17-19

Where: Union Park

Who: For your Chicago fix: early money is on Wilco but smart money is on Chance the Rapper (my favorite live performer in the history of my life) and SAVEMONEY comrade Vic Mensa. Portlandia fans should go see Sleater-Kinney just to get an Instagram of Carrie Brownstein. But the show you can’t miss? Freddie Gibbs & Madlib. TRUST! 

Eaux Claires

When: July 17-18

Where: Eau Claire, WI

Who: Bon Iver reunion. In Justin Vernon’s town. In a grassy field. DON’T BE A DINGUS!


When: July 31-August 2

Where: Millennium Park

Who: Ah, the sloppy Chicago standby. Artists with big font size on the poster: Paul McCartney (just to say you were there), Alabama Shakes, Alt-J and A$AP Rocky. Artists with small font size on the poster: Raury, Mick Jenkins and SZA.

Chicago Jazz Festival

When: September 3-6

Where: Millennium Park and Chicago Cultural Center

Who: This year’s festival honors 100 years of Billie Holiday so go see José James playing the music of Billie Holiday.

North Coast Music Festival

When: September 4-6

Where: Union Park

Who: Low key festival, high key lineup: must-sees include D’Angelo, Action Bronson, Future Islands, Washed Out and The Youngblood Brass Band.

Riot Fest

When: September 11-13

Where: Douglas Park

Who: Blow summer into the wind to the smooth sounds of Snoop Dogg, turn up one last time to Chicago-native Alex Wiley or go out in true TDH fashion and rock out to our newest Production Artist Dave jamming with his band The Arrivals.

Just remember kids, apply sunscreen and drink lots of water. Now, in the spirit of partying, music and Chicago, I’ll close with the words of our sonic Lord and Savior Yeezus: “Summertime Chi, ahhhh. Now throw your hands up in the sky!”


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