Chicago’s Best Outdoor Summer Festivals: Fun Music, Food, Dance

Joyful pleasures and summer treasures are already in the air! Across the United States, peak festival season kicks off now. In Chicago — the mecca of music, food, drink, crafts, art, dance — its 2022 outdoor festivities have kicked into high gear. Over the next three months, more than two dozen major events, as well as dozens of community fairs and festivities, salute the colossal cultural and culinary talents of Windy City. It can be pleasantly dizzying to choose from so many mind-blowing activities, great must-sees and free entertainment. Check Choose Chicago for animated programming, as well as other useful details for planning your trip. Presented by the Chicago Department of Cultural Affairs and Special Events, the full program is at Here’s the lowdown on a handful of favorite highlights.

Chicago Blues Fest

Chicago Blues Fest (June 9 to 12). Where: The Jay Pritzker Pavilion in Millennium Park, as well as at various stops in the neighborhood. Best bets: This city-wide blues-boost is the biggest Admission fee gathering of blues around the world, saluting Chicago’s blues-born heritage. Applaud a luminous assemblage of masterful musicians, such as Billy Branch & The Sons of Blues, Eric Gales (also known as Raw Dawg), Grady Champion, Joanna Connor, Rico McFarland, The Kinsey Report, The Mike Wheeler Band, Thornetta Davis and Toronzo Canon. During each of the four days, a different tribute theme is also deployed, acclaiming the achievements of distinctive artists: Erwin Helfer and The Boogie Woogie Ensemble, Bob Stroger & Friends, Chicago Soul and Women in Blues.

Grant Park Music Festival

Grant Park Music Festival (June 15 to August 22). Where: The Jay Pritzker Pavilion in Millennium Park; seated ticketing fees, as well as free spaces available. Best bets: Say it, “Wow!“This amazing program is very uplifting and has been heralded as a transformative artistic extravaganza. It features spectacular classical pieces, such as Beethoven Heroic Symphony, Tchaikovsky Sleeping Beauty and Rachmaninoff Piano Concerto No. 2, as well as popular contemporary selections at Independence Day Salute and Lights on Broadway. His The Circus goes to Hollywood spotlights live aerials performing incredible feats above the stage.

Millennium Park Summer Music Series

Millennium Park Summer Music Series (June 20 to August 18). Where: The Jay Pritzker Pavilion in Millennium Park; free. Best bets: Prepare to be thrilled by the rousing roster of American and global artists, such as DakhaBrakha, a folk-fusion quartet from Kyiv, Ukraine; Femi Kuti, Nigerian afrobeat saxophonist; the Chicago Immigrant Orchestra, a 12-piece ensemble expressing musical flair harvested from around the world; Cimafunk, an Afro-Cuban voice that skilfully blends funk with Cuban music and African rhythms; Abigail Washburn, an Illinois-born, Nashville-based singer-songwriter and clawhammer banjo player; and Samantha Crain, from Oklahoma, Choctaw singer-songwriter, poet and musician, two-time Native American Music Award winner.

Chicago SummerDancing

Chicago SummerDancing (July 6 to September 17). Where: Pop-up events downtown and across the city; free. Best bets: This beloved series, led by professional dance teachers, teaches attendees of all ages and skills how to get out and in. Learn memorable moves: afrobeat, bachata, ballroom basics, east coast swing, hula, line dancing, merengue, polka hop, salsa and more. Expect lots of smiles and upbeat rejoicing.

Taste of Chicago

Taste of Chicago (July 8 to 10). Where: Grant Park along Buckingham Fountain, with over 30 vendors; FREE ENTRANCE. Best bets: Food galore! Entertainment is also on the agenda: three stages with free musical performances, including Aterciopelados (a Colombian rock band), Drive-By Truckers (an American rock band based in Athens, Georgia) and Sadie Woods, originally from Chicago (artist and DJ) — plus dance sessions and family entertainment. Additionally, a series of three Taste pop-up events are taking place on back-to-back Saturdays in neighborhoods from Chicago to Austin (June 11) featuring Caribbean bites, tacos, gumbo; Pullman (June 18) with ribs, artisan sandwiches, gourmet sausages; and Little Village (June 25) with Mexican-style popsicles, macaroni and cheese, and gazpacho, among other delicious dishes.

Hearty appetites flock to this feast-a-thon, founded in 1980. It sets iconic Midwestern tunes on fire and features innovative treats. Chicago’s vibrant and diverse restaurants are represented including: Arun’s Thai Restaurant, Auntie Vee’s Kitchen, Barangaroos Aussie Pies, BJ’s Market & Bakery, Buona Beef, Chicago’s Doghouse, Churro Factory, Classic Cobbler Baked Goods Company, Connie’s Pizza, Cynthia’s Gumbo Express, Decadent Flavor, Doom Street Eats, Eli’s Cheesecake Company, Esperanza Kitchen Delights, Haire’s Gulf Shrimp, Healthy Substance, Josephine’s Cooking, La Cocinita Food Truck, Mr. Quiles Mexican Food, Mr. E Chef Catering, Mrs. Tittle’s Cupcakes, Original Rainbow Cone, Prime Tacos, Franco’s Ristorante, Robinson’s No.1 Ribs, Seoul Taco, Taco Sublime, Tandoor Char House, The Sole Ingredient Catering, Whadda Jerk and Yum Dum. The thirst-quenching bonus: a brasserie, a wine cellar and a cocktail bar.

“After an all-virtual Taste in 2020 and community pop-ups in 2021, we are excited to bring Taste back to Grant Park and our neighborhoods in 2022,” said Erin Harkey, Commissioner of the Department of Cultural Affairs and Special Events. “There’s something for everyone to enjoy at this year’s Taste, citywide.”

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