Chicago music festivals boast must-see legendary lineups this summer

Lollapalooza returns to Grant Park — Photo courtesy of Ismael Quintanilla III for Lollapalooza

Music fans know that Chicago is the best city for summer music festivals, as there is an abundance of world-class entertaining events happening all around the city. When the temperature rises, the Windy City comes alive with many new and legendary musical acts, performing at various iconic venues around town.

If you’re traveling to Chicago, you’re in luck! There’s so much to see and do in the area beyond these major musical events, as this fantastic city features unparalleled architecture, a beautiful lakefront, easy transportation, friendly citizens and a vast array of dining options.

Check out these noteworthy Chicago music festivals and learn a local’s insider tips to best enjoy them.

Do Division Street

Do Division Street kicks off summer festival seasonDo Division Street kicks off summer festival season — Photo courtesy of Niko Sulek

Kicking off the city’s 2023 festival season on June 2-4, Do Division Street Fest welcomes more than 30 bands on two stages programmed by two Windy City live music venues: The Empty Bottle and Subterranean. Fest goers appreciate the variety of indie shops, delectable food offerings and ice cold beer, including brews from local favorite Goose Island Beer Co.

The inclusive event welcomes little rockers, too, with a dedicated “Do Division Family Fun Fest.” (Don’t miss “Do Chicago Fashion Fest” with local designer runway shows and vendors.)

Tip: For a trippy vibe, visit The Cauldron, a brand-new magic and wizard-themed restaurant and bar that’s nearby, featuring a Potion-Making Experience that combines high-tech magic wands and molecular mixology for drinks that bubble, smoke and change color.

Chicago Blues Festival in Millennium Park

Los Lobos will perform at the free Chicago Blues FestivalLos Lobos will perform at the free Chicago Blues Festival — Photo courtesy of Piero F. Giunti

More than a half-million fans gather over four days for the free Chicago Blues Festival in Millennium Park. The 40-year-old festival shines again on June 8-11 with a 2023 line-up that includes Blind Boys of Alabama, Los Lobos, Eddie Cotton and a Centennial Tribute to Albert King featuring Donald Kinsey, Larry McCray, Rico McFarland and other top performers.

Be sure to see what’s happening at the Visit Mississippi Juke Joint Stage. Peek into Rosa’s Lounge, which features a daily showcase of Chicago blues legends and new artists who have been calling Rosa’s home for nearly 40 years.

Tip: To picnic at the fest, grab an Asian noodle salad, Mediterranean bento box, falafel bowl, avocado summer roll or a spicy turkey and cheddar sandwich, plus all kinds of snacks and drinks, at Chicago’s popular convenience store, Foxtrot. (The Streeterville store is nearest the park.)

Windy City Smokeout

The best barbecue and country music equals one fine Chicago festivalThe best barbecue and country music equals one fine Chicago festival — Photo courtesy of Windy City Smokeout

Windy City Smokeout — recognized twice as the “Festival of the Year” by the Academy of Country Music Awards and No. 2 in USA Today’s Readers’ Choice for Best Specialty Food Festival — celebrates its 10th year in 2023 with performances by GRAMMY Award winners Zac Brown Band and Darius Rucker, Luke Bryan, Zach Bryan, Jo Dee Messina and other major artists.

Attendees will enjoy some of the country’s best craft beer, while over 30 pro “pit masters,” hailing from Texas, Missouri, New York, California, Kansas, Arkansas, Tennessee, Illinois and points in between will be smoking and cooking throughout the entire event. 2023 dates are July 13-16.

Tip: You’ll need a solid place to lay your body down after a day of beer, barbecue and songs about cheatin’ hearts and pickup trucks. Just a little over a mile away, Nobu Hotel Chicago is the epitome of serenity. Or, for deals on last-minute bookings on professionally managed homes and condos look into Whimstay.

Pitchfork Music Festival at Union Park

More than 60,000 music fans enjoy 40-plus bands over three days at Pitchfork Music FestivalMore than 60,000 music fans enjoy 40-plus bands over three days at Pitchfork Music Festival — Photo courtesy of Julian Bajsel

Since 2006, Pitchfork Music Festival has been expanding psyches by bringing the finest emerging artists and musical luminaries to the stages at Chicago’s Union Park. In 2023, fans look forward to the US debut of The Smile (which includes Radiohead members, Thom Yorke and Jonny Greenwood), as well as sets by 700 Bliss, Big Thief, indie icon Bon Iver, Panda Bear, Alvvays — just a few of the more than 40 acts playing July 21-23. Count on an array of quirky vendors, local food and a specialty record fair.

Tip: A 15-minute walk from the park, WNDR Museum houses the U.S. debut of the yellow Dots Obsession, a three-story immersive infinity installation by iconic artist Yayoi Kusama. The exhibit features floating yellow and black polka dots alongside walk-in and peep-in installations that may make you feel positively celestial.

Lollapalooza in Grant Park

Kendrick Lamar, Billie Eilish, Diplo and and Lana Del Rey take the Lolla stage in 2023Kendrick Lamar, Billie Eilish, Diplo and and Lana Del Rey take the Lolla stage in 2023 — Photo courtesy of Charles Reagan for Lollapalooza

Look up the word “lollapalooza” and you’ve got the gist of this massively popular festival that began in 1991 by Perry Farrell of Jane’s Addiction. This year’s Lollapalooza, slated August 3-6, includes over 170 bands on nine stages for four full days of music and programming in Chicago’s Grant Park. Headliners include Billie Eilish, Karol G, Kendrick Lamar, The 1975, Odesza, Red Hot Chili Peppers and others.

This world-famous festival has become a tradition for so many music fans and attracts thousands of attendees from across the globe. If you’re planning to go, be sure to pay close attention to the concert schedule, as bands play on a variety of stages simultaneously. It’s best to purchase tickets in advance and reserve your accommodations before arriving in the city, as many hotels tend to sell out.

Chicago Jazz Festival on Labor Day Weekend

The free Chicago Jazz Festival is a Labor Day weekend traditionThe free Chicago Jazz Festival is a Labor Day weekend tradition — Photo courtesy of Chicago DCASE

For more than 40 years, the free admission Chicago Jazz Festival showcases a diverse lineup of modern music wizards and jazz legends. It’s a fun Labor Day weekend tradition that brings all that jazz to Millennium Park, the Chicago Cultural Center and various other venues in the city. 2023 dates are August 31 to September 3.

Tip: You never know who might take the stage at The Jazz Showcase, the oldest historic jazz club in Chicago that still thrives. The downtown venue has witnessed the genius of legends from Dexter Gordon and Yusef Lateef to Dizzy Gillespie and Art Blakey.

More Chicago music festivals this summer

ARC Music Festival is an immersive journey into dance musicARC Music Festival is an immersive journey into dance music — Photo courtesy of Courtesy of ARC Music Festival // KURSZA

Other notable music fests in town include Heatwave, a two-day dance music blowout and ARC Music Festival that celebrates the birthplace of house music. Meanwhile, alt rock and punk fans will head to Riot Fest in September.

Do you have an aversion to crowds? The city’s neighborhood festivals will give you a sweet sense of Chicago’s welcoming residents, stellar food and drink, interesting vendors and local artists. Chicago’s Little Italy Festa and Andersonville Midsommarfest fit the bill, or check out the list to see what’s cooking during your visit.

Where to stay? Virgin Hotels Chicago, in the heart of the Loop, is a short walk from Millennium Park. Throughout festival season, the hotel hosts many fun events, including themed after parties with DJ entertainment, on-site hairstylists (with braid bars) and pre-festival brunch events.

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