Austin may get most of the attention, but Chicago is one of the best places in the world for live music. The biggest names play Soldier Field, Wrigley Field, the United Center, and festivals like Lollapalooza. But there are also several smaller venues across the city, including the iconic Chicago Theater—the first large, lavish movie theater in the U.S. and where I saw Elvis Costello live.
Chicago is a city that’s made for music tourism, and whatever kind of performance you’re looking for, you can find it here. Experience the Chicago Blues at Kingston Mines in Lincoln Park. Catch live jazz at the Green Mill in Uptown, a former hangout of Al Capone’s, or Andy’s Jazz Club near the DuSable Bridge. See a show at the intimate 250-seat City Winery in Fulton Market. Catch a rock band at Schubas Tavern in Lakeview, or see a free show at the Pritzker Pavilion.
For The Biggest Names
United Center isn’t just the home of the Chicago Bulls and Chicago Blackhawks. It’s also where performers you’ll find performers like Madonna, Justin Timberlake, Katy Perry, Olivia Rodrigo and Dua Lipa.
When it’s not football season, the Chicago Bears clear out of Soldier Field to make room for performers like Billy Joel, Stevie Nicks, Metallica, The Rolling Stones, Taylor Swift and Beyonce.
Pearl Jam, Bruce Springsteen, Lady Gaga and Paul McCartney have all played at Wrigley Field, the baseball stadium that’s home to the Chicago Cubs.
Look for smaller shows at the Vic Theater or Schubas Tavern in Lakeview, Lincoln Hall in Lincoln Park, Thalia Hall in Pilsen, Concord Hall in Logan Square, and the Aragon Ballroom in Uptown. Chicago Theater and the Auditorium Theater also host live musical performances.
The newest live music destination in Chicago is the Near North Side where you’ll find The Salt Shed and Outset. The Salt Shed is inside what used to be a Morton’s Salt Factory, and there’s a cannabis lounge onsite.
My favorite venue in town is City Winery. Catching a show at the venue, which seats under 250 people, feels like watching a performance in your friend’s living room. And the lineup might surprise you.
For Dive Bar Vibes
Nothing says Chicago like a good dive bar, except maybe a good dive bar with a stage. For local musicians, indie bands and alternative rock groups, check the schedules at Subterranean in Wicker Park and Empty Bottle in Ukrainian Village.
Subterranean is just off the Blue line El train between Chicago O’Hare International Airport and downtown.
If you’re in Chicago for an event at McCormick Place, it’s about a fifteen-minute walk to Reggie’s, a lively restaurant and bar with a rock club and recording studio.
Chicago Live Music Map
For Jazz
Jazz began to make its mark on Chicago around 1915, and the city is still one of the best places to experience American jazz music. Chicago even has its own style of jazz, a combination of Mississippi Delta and New Orleans Dixieland styles.
In River North, head to Andy’s Jazz Club or the Tortoise Supper Club. For a more historic vibe, go to Jazz Showcase in the loop. Jazz Showcase has been open since the late 1940s, and its stage has hosted jazz legends like Count Basie and Dizzy Gillespie. Kids get in free to the family-friendly Sunday matinee.
Head Uptown to see a show at the Green Mill, a former speakeasy that was a favorite of Al Capone’s. Green Mill has been hosting live jazz since the 1930s, and catching a show here is one of the best ways to spend a night in Chicago.
For Blues
Like jazz, Chicago put its own twist on the Blues. Riffing off the Delta blues, Chicago musicians created their own signature sound, one that would reverberate across genres providing a foundation for the development of soul music and rock ‘n roll.
Get a taste of the Chicago blues by catching a show at Kingston Mines, an epicenter of the Chicago blues community and the city’s oldest and largest continuously operating blues club. This Lincoln Park blues club opened its doors in 1968 and hosts live music every night of the week.
It’s also not far from Weiner’s Circle, Chicago’s legendary hot dog spot, and one of the city’s most popular late-night eats.
Or head to the other epicenter of the local blues scene, Buddy Guy’s Legends. This downtown blues club is an ode to the blues legend Buddy Guy, a GRAMMY award winner known for his influence on other musical legends including Jimi Hendrix, Eric Clapton and Stevie Ray Vaughan. Guy still plays a concert at his namesake club each January.
Free Live Music
You don’t have to be wealthy to afford live music in Chicago. Just visit during the summer when the city has a full calendar of free concerts.
The Chicago Blues Festival takes place in Millennium Park each June. It is the largest free blues festival in the world. B.B. King, Ray Charles, Buddy Guy and Etta James have all played at this festival. Chicago hosts the free Chicago Jazz Festival each Labor Day weekend. It also hosts free house music and gospel music festivals.
The Grant Park Music Festival takes over the Jay Pritzker Pavilion in Millennial Park for the nation’s largest free classical music festival. Check the festival website for dates and performers.
Millennium Park hosts its own free concert series with weekly shows featuring local, national, and international artists. The Museum of Contemporary Art hosts free jazz performances on its terrace between late June and late August.
Neighborhood festivals like Wicker Park Fest and Belmont-Sheffield Music Festival are great options for free shows by local performers.
Chicago Music Festivals
Summer in Chicago means musical festival season, and this city puts on shows worth traveling for. If you travel for the blues, visit in June during the Chicago Blues Festival. If jazz is more your speed, plan your trip over Labor Day weekend when the city hosts the Chicago Jazz Festival.
The biggest event of the year is Lollapalooza, a multi-day multi-genre festival that attracts several hundred thousand music fans each year. This is one festival that always sells out and sends downtown hotel prices soaring, so plan ahead. And don’t miss out on the after-shows held at venues around the city.
If you’re looking for punk, heavy metal and lots of points in between, plan your trip around Riot Fest, which happens each September. For reggaeton, visit for Suenos in May. The Hideout Block Party raises money for local charities and draws surprisingly big names to an intimate backyard-style setting. I once saw Wilco, Iron & Wine and Belle & Sebastian at a Hideout Block Party.
Meena Thiruvengadam co-authored the 2025 edition of the Lonely Planet Chicago guidebook.
