Below is just a sample of the summer events you'll find throughout Chicago: 

• Chicago Pride Fest (June 21-22, 2025) - Each year, more than 100,000 revelers flock to the historic LGBTQ+ neighborhood of Northalsted to take part in the festivities, including three stages with live music, more than 100 arts and crafts vendors, food from local restaurants, drag shows, dance performances, a high-heel race, and more. This year's headlining artists include Natasha Bedingfield, JoJo Siwa, Sapphira Cristál, Bob the Drag Queen, Amber Riley, and more across two stages. 

• Argyle Night Market (Every Thursday from July 3 - August 28, 2025) - Started in 2013 by Uptown United, the Argyle Night Market is an annual event that features food from local Argyle restaurants plus live cultural and musical performances on Thursday evenings each summer. This vibrant and award-winning event is located on Argyle, the city's first shared street, which prioritizes pedestrians, celebrates green infrastructure, and encourages community engagement.

• Windy City Smokeout (July 10-13, 2025) - The nation's premier outdoor country music and BBQ festival returns to Chicago's iconic United Center for its 12th year. The star-studded weekend will feature country music's biggest names, including Kane Brown, Old Dominion, Jon Pardi, Bailey Zimmerman, and Megan Moroney, along with an impressive roster of up-and-coming talent and over 25 of the best BBQ teams from across the country. In addition to the top performer in country music, the festival offers a selection of curated events, such as the “Biggest Happy Hour of the Summer” on Friday, July 11 and an epic “BBQ Brunch” on Sunday, July 13 from 11:30 a.m. to 1 p.m. The bottomless BBQ Brunch will include a variety of dishes from the Windy City Smokeout's Pitmaster Buffet, featuring a special Bacon Bar. Guests can also sip on mimosas and build their own Bloody Marys with all the fixings at the Bloody Mary Bar.

• Chinatown Summer Fair (July 26-27, 2025) - This iconic event is one of the most ethnically unique outdoor events in Chicago and the Midwest. Attracting more than 50,000 people from throughout the region, Chinatown Summer Fair is a true celebration of Far East beauty and culture including food, art, and music. This neighborhood street festival will open with a lion dance procession, followed by Asian performances; kung fu demonstrations; samplings from Chinatown's restaurants and unique gift shops; arts & crafts exhibits; street vendors with an array of merchandise; and a children's area.

• Lollapalooza (July 31 - August 3, 2025) - One of Chicago's most highly anticipated summer events, this genre-defying lineup is packed with the music industry's biggest names, along with local favorites and emerging artists.The full Lollapalooza lineup features more than 170 musical acts across nine stages, with headliners such as Olivia Rodrigo, Tyler, the Creator, Sabrina Carpenter, Rüfüs du Sol, Luke Combs, A$AP Rocky, Gracie Abrams and Doechii

• Chicago Air and Water Show (August 16-17, 2025) - The Chicago Air and Water Show has been an iconic Chicago event since 1959. The annual summer spectacle is the largest and oldest free-admission air and water exhibition in the United States. The two-day event draws an audience of over one million to the city's stunning lakefront to see pilots perform astonishing stunts above the waters of Lake Michigan.

• Chicago House Music Festival and Conference (August 22-23, 2025) - The Chicago House Music Festival is an annual celebration of the Chicago-born genre that has revolutionized dance music globally. Held in Millennium Park every summer, this joyous event attracts house fans from across the globe to hear today's top DJs and up-and-coming talent.

• Chicago Jazz Festival (August 28-31, 2025) - The Chicago Jazz Festival is a Labor Day weekend tradition that promotes all forms of jazz through free, high-quality music programming at Chicago Cultural Center and Millennium Park. The festival showcases Chicago's local talent alongside national and international artists to raise awareness and appreciation for one of the city's most beloved art forms.

For the ultimate guide to summer festivals, you can expect to see in Chicago, please visit: https://www.choosechicago.com/articles/chicago-music/top-summer-music-festivals-in-chicago/