From Taste of Chicago to Lollapalooza, the Windy City knows how to throw a good fest. Don’t forget to mark these standout summer festivals on your calendar.
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Date: Fri., May 16 - Sun., May 18
Located in the historic district of Lincoln Park, this festival will feature two stages with live music from artists including Sixteen Candles, School of Rock Chicago, One Night Band and more. The heart of the event is the Spring Fine Art Mart, which showcases local visual artists and features live interactive demonstrations. A $15 cash-only donation is suggested and can be made at the gate. 1000 W. Armitage Ave.
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Date: Sat., May 24 & Sun., May 25
Founded in 2022 by the producers of Baja Beach Fest in collaboration with C3 Presents (the production team behind Lollapalooza), this Grant Park music festival celebrates Latin music, culture and cuisine with an emphasis on reggaeton and Latin trap. This year’s headliners include icons like Shakira, Don Omar, Peso Pluma, Grupo Frontera and more. 337 E. Randolph St.
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Date: Fri., May 30 - Sun., June 1
Enjoy three days of live music programmed by local venues The Empty Bottle and Subterranean, accompanied by food trucks, a fashion presentation and family-friendly events for guests of all ages. Division Street, Between Ashland Ave. & Leavitt St.
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Date: Thurs., June 5 - Sun., June 8
The annual Blues Festival is a summertime must for music fans, with four stages and over 40 performances from more than 250 artists. Pay tribute to the city’s oldest musical tradition and listen to some of the best blues, soul, R&B, gospel, rock and hip-hop creators in Millennium Park, including Chicago icon Mavis Staples, Grammy Award-winning musician Bobby Rush, Chicago Blues Revival and more. 201 E. Randolph St.
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Date: Fri., June 6 - Sun., June 8
Celebrate the art of barbecue with this event, featuring 50,000 pounds of pork and more than 20 food vendors. Roam the vendor-filled streets of Lincoln, Damen and Irving Park Road and enjoy some of the world’s best barbecue, accompanied by live music. 4000 N. Lincoln Ave.
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Date: Fri., June 13 - Sun, June 15
Celebrate Swedish culture with three days of street revelry, including live music, unique vendors, food stands and activities for the whole family. All proceeds from donations and beverage sales go toward the Andersonville Chamber of Commerce, and a portion of donations directly support over a dozen local nonprofit organizations, including the Peirce and Chappel Elementary Schools, the Chicago Women’s Health Center, the Brave Space Alliance and more. 5217 N. Clark St.
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Date: Sat., June 14 & Sun, June 15
This neighborhood festival features an artist gallery, food vendors, a garden walk, a children’s corner and live music performances from artists like Fifth Star Band, Soulbillys, North Park Strummers and more. The event showcases fine art from more than 200 artisans in mediums like drawings, painting, photography, mixed media, printmaking, glasswork, ceramics, fiber, jewelry and woodwork. 1763 N. North Park Ave.
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Date: Sat., June 21 & Sun., June 22
Get a head start on Pride with this festival, which takes place one weekend before Chicago’s Pride Parade. Explore three live music stages, drag shows, dance exhibitions, guest speakers, pet parades and over 150 food and merchandise vendors. A $20 cash-only donation is suggested and can be made at the gate. Halsted Street, Near The Intersection of North Halsted St. & West Addison St.
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Date: Thurs., July 10 - Sun., July 13
With country music and barbecue from the city’s top pitmasters, Windy City Smokeout is a guaranteed good time. Headliners this year include big names like Kane Brown, Bailey Zimmerman, Old Dominion, Riley Green and more. 1901 W. Madison St.
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Date: Thurs., July 31 - Sun., Aug. 3
Chicagoans and visitors worldwide couldn’t get enough of Lollapalooza—so they added a fourth day in 2016. The iconic annual Grant Park fest always offers a stellar lineup on all eight stages and some of the city’s best bites. This year, more than 170 acts, including headliners Sabrina Carpenter, A$AP Rocky, Olivia Rodrigo, Tyler, The Creator and Luke Combs, are on the roster. 337 E. Randolph St.
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Date: Sat., Aug. 9 & Sun., Aug. 10
This year is the street festival’s 43rd iteration, and it features a half-mile of five stages and more than 250 vendors selling arts, crafts, food and drinks. Plus, the weekend includes dance exhibitions and drag performances, so there’s something in store for everyone. Halsted Street from Belmont Ave. to Addison St.
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Date: Sat., Aug. 16 & Sun., Aug. 17
Chicago’s Air & Water Show is a beloved annual tradition that draws thousands to the lakefront each year, featuring military performers, including the U.S. Air Force F-16 Viper Demo Team, the U.S. Air Force Heritage Flight Demo Team, the U.S. Navy Super Hornet Demo Team and more. This action-packed event thrills with spectacular plane maneuvers and boat shows. 1600 N. Lake Shore Drive
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Date: Thurs., Aug. 28 – Sun., Aug. 31
To bring awareness to the art of jazz and provide access to all, the Chicago Jazz Festival has hosted some of the best musicians in the biz for over 40 years and is a perfect way to close out the summer. This year will include performances from an array of legendary jazz icons and emerging artists. 201 E. Randolph St.
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Date: Fri., Aug. 29 - Sun., Aug. 31
This Bridgeview-based music festival is celebrating its 15th anniversary this year with a lineup of headliners like Zedd, Excision, REZZ, Chris Lake, RL Grime, Zeds Dead, Seven Lions and more. Along with a range of electronic, hip-hop, folk, jam band and rock acts, the weekend also showcases performance and installation artists. 7000 S. Harlem Ave., Bridgeview
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Date: Fri., Sept. 5 - Sun., Sept. 7
Since 1980, this Grant Park food festival has offered guests the chance to try eats and drinks from some of the best Chicago restaurants. This year, there will be three live music stages and food from over 40 city eateries. Grant Park, Buckingham Fountain Plaza
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Date: Fri, Sept. 19 – Sun., Sept. 21
With an emphasis on rock, punk, alternative, hip-hop and metal music genres, this three-day music festival has remained a cornerstone of the city’s subculture scene since its 2004 inception. Visit to enjoy live performances, carnival rides, food vendors, merchandise booths and more. Douglass Park at The Corner of Ogden Ave. and Sacramento Drive
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Date: Fri., Sept. 26 – Sun., Oct. 5
The World Music Festival Chicago has been a cherished event for over twenty years, featuring over 31 musicians from 16 countries. Well-known instrumentalists and emerging artists will perform at 11 venues throughout the city this year, including the Chicago Cultural Center, Millennium Park and Navy Pier. Multiple locations
See also: The 10 Best Farmers Markets In Chicago
Photography by: Photography by Gary Miller, courtesy of Getty Images
