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The 2019 Chicago Blues Festival in Millennium Park, June 2019.
Millennium Park; photo courtesy city of Chicago

Top Chicago spring and summer festivals

Chicago’s festival season heats up with the arrival of warm weather. May though August is a great time to bring your group to the city and attend some of the most anticipated free and ticketed events of 2023. From watching the first urban NASCAR race zoom through downtown streets to listening to live blues and joining in Pride Month celebrations, Chicago offers something for every group.

Free festivals

During the Millennium Park Summer Music Series, held from June 22 – Aug. 21, watch diverse performers and groups as they bring a variety of rhythms to the Jay Pritzker Pavilion stage on Monday and Thursday evenings. You’ll hear a range of music, from jazz and hip-hop to world beats, pop, and everything in between.

Classical music never sounded so good during free summer concerts at Millennium Park’s Jay Pritzker Pavilion. Under the umbrella of the Grant Park Music Festival, the Grant Park Orchestra opens its series with Schumann Symphony No. 4 on June 14. Other shows include a patriotic lineup for An American Salute: Rhapsody in Blue on July 5, powerful vocalists performing in the Bravo Broadway program July 28 – 29, and aerialists accompanying the orchestra for Cirque Returns on Aug. 9. The Grant Park Orchestra and its chorus close the season with Rachmaninov Symphonic Dances from Aug. 18 – 19.

Pride Fest
Chicago Pride Fest

There are scores of exciting LGBTQ+ events held throughout the year in Chicago, but Pride Month promises fun-filled weekends in June. Must-attend events include the two-day Chicago Pride Fest in the Northalsted neighborhood June 17 – 18, the Pride in the Park outdoor music festival on June 23 and 24 in Grant Park, and the four-mile Chicago Pride Parade, stepping off on June 25 from Halsted and Broadway streets.

On June 3, listen to the rousing sound of voices lifted in praise during the Chicago Gospel Music Festival in Millennium Park. Hear inspirational music by performers ranging from top traditional choirs to contemporary artists.

Catch the world’s best blues musicians at the Chicago Blues Festival in Millennium Park, held from June 8 – 11. Up-and-coming talent and established virtuosos perform during this Chicago tradition that’s also the city’s largest music festival. With 500,000 people attending, your group will want to arrive early for seating in the Jay Pritzker Pavilion or on the Great Lawn.

Chicago Air and Water Show
Chicago Air and Water Show

Spectators flock to the Lake Michigan shoreline for the annual Chicago Air and Water Show, held Aug. 19 – 20. Stake your group’s viewing spot along the beach between Oak Street and Fullerton Avenue. Watch daredevil acrobatic maneuvers, see members of the U.S. Army Golden Knights parachute team land on North Avenue Beach, and marvel at the sight and roaring sound of a precision performance by U.S. Air Force Thunderbirds fighter jet pilots.

Ticketed events

Sueños Music Festival
Sueños Music Festival

Watch top Latin and reggae performers at the Sueños Music Festival from May 27 – 28 in Grant Park. First-day headliners at the age 18+ event are Wisin y Yandel and Feid. Closing day highlights include performances by Grupo Firme and Nicky Jam. Over the two days, see 14 other bands on the main stage and watch DJs spin tunes. Between sets, visit food vendors, bars, and merch stores, and get a bird’s-eye view of the event on a Ferris wheel ride.

Like fast cars and live music? Hear the thunder of engines revving July 1 – 2 during the inaugural Chicago Street Race, part of the NASCAR Cup Series. During the NASCAR Chicago Street Race Weekend festivities, see top drivers exceed 100 mph on the 2.2-mile (3.5 km) course that winds through Grant Park and surrounding downtown streets. Meet drivers, admire cars parked along the pit lane, and catch concerts featuring The Chainsmokers, Miranda Lambert, The Black Crowes, and Charley Crockett.

Windy City Smokeout Chicago
Windy City Smokeout

From July 13 – 16, enjoy your fill of country bands, barbecue, and beer when Windy City Smokeout takes over the grounds of the United Center. Top pitmasters serve up their best barbecue. Wash down your ‘cue with a cold craft beer from local and national breweries. Country music superstars headlining the festival include Luke Bryan, the Zac Brown Band, Zach Bryan, and Darius Rucker.

Lollapalooza ©Experience by Pooneh Ghana
Lollapalooza ©Experience by Pooneh Ghana

Rock out at Chicago’s iconic Lollapalooza music festival from Aug. 3 – 6 in Grant Park. Nine stages host more than 170 bands, ranging from metal to punk, pop, rap, R&B, and more. Premium experiences include seats with prime viewing, food and beverage packages, air-conditioned lounges, and golf cart shuttle service between venues.

Learn about more upcoming Chicago festivals.

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