Friday 16 April 2021
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The Big City Blog: The Chicago festivals not to miss this summer

It’s officially summer festival season, and we’ve put together a little list of what to look forward to

By Brian Burke


Chicago Kids and Kite Festival: On May 2, the 17th annual Chicago Kids and Kite Festival will provide free kite kits and other activities for children. The event will be located at Cricket Hill in Lincoln Park. Admission is free. Visit here for more information.

Chicago Zine Fest: A literature festival on May 8-9 offers free workshops in comics, poetry and button-making. Admission is free and open to the public. Friday will be at 115 W. Chicago Ave., and Saturday will be at 1340 W. Washington. Visit here for more information.

Chicago Craft Beer Week: The fifth annual Chicago Craft Beer Week has more than 300 venues participating from May 14-24. The theme this year is “Chicago: A City of Neighborhoods.” Visit for more information.

Belmont-Sheffield Music Festival: On May 23-24, located right off the Belmont red Line, the Belmont-Sheffield Music Festival will celebrate its 31st anniversary with a variety of performers. Click here for more information.


Photo: Adam Alexander Photography

Bike the Drive: On Sunday, May 24, the MB Financial “Bike the Drive” will open Lake Shore Drive to bikers. Visit to sign up.

Maifest: From May 28-31, Maifest will host a weekend of German food and cultural entertainment at Lincoln and Leland Avenues. For more information, visit

Millennium Art Festival: Ambur’s Millennium Art Festival will bring art festivities to Lake St. and Michigan Ave. downtown from May 29-31. Visit here for more information.

Chicago Gospel Music Festival: The 30th annual Gospel Music Festival will showcase multiple performers in Millennium Park from May 29-31. For the schedule and more information, visit here.

Do Division Street Fest & Sidewalk Sale: Original live music, family activities, independent retailers and artisans in West Town from May 29-31. Visit for more information.


Taste of Little Village: Flavors of Mexico: From June 5-7, authentic Mexican food will be sold at the Taste of Little Village at 26th & California. There will be a Mexican carnival for children. Visit here for more information.

Pilsen Food Truck Social: On 18th Street from Racine to Throop, more than 25 Chicago trucks will be stationed for this social June 6-7. For truck and general information, visit There’s a $5 optional donation to benefit the Illinois Food Truck Owners Association and Saint Procopius food bank and soup kitchen.

Printers Row Lit Fest: From June 6-7, a two-day showcase with more than 200 authors, 200 booksellers and 150,00 book lovers. You can find the fest on Dearborn, from Congress to Polk. To reserve tickets and for more information, visit

Ribfest Chicago: On June 12-14, Ribfest Chicago will take place at the Lincoln/Damen/Irving intersection with more than 30 vendors grilling and smoking tons of ribs, pulled pork, brisket, etc. Visit for the schedule and more information.

Photo: Adam Alexander Photography

Photo: Adam Alexander Photography

Chicago Blues Festival: The world’s largest free blues festival returns to Grant Park June 12-14. For more info on the 32nd annual event, visit here. Admission is free.

Spring Awakening Music Festival: Catering to electronic dance music fans, Spring Awakening will return to Solider Field June 12-14. For the lineup, tickets and more information, visit

The Old Town Art Fair: One of the most earthy art festivals in Chicago, the Old Town Art Fair takes place on June 13-14 at Lincoln Avenue and Wisconsin St. Along with the 250 artists, the fair includes a garden walk of 60 urban home gardens, music, food and children activities. Visit here for more information.

Taste of Randolph Street: From June 19-21, head to the West Loop for live music, a ton of food and after-parties. Check for the lineup and more information. There will be a DJ dance stage hosted by The Mid. After-party tickets are available for purchase on the site.Chicago-Festivals&Parades_AA_PRIDE_07 WEB

Chicago Pride Fest/Pride Parade: The Boystown neighborhood will be throwing its massive two-day LGBT festival on June 20-21. A week later, on June 28, the annual Pride Parade will be held down N. Halsted and meandering through the north side. For more information, visit

Chicago SummerDance: Every weekend from June 26-September 13, there will be dance lessons and live music at the Spirit of Music Garden in Grant Park. Visit here for more information. Lessons and admission are free.

World’s Largest Block Party: On June 27, the self-proclaimed “World’s Largest Block Party,” will throw another huge celebration at its new location, the UIC Festival Lot. Artist include Young the Giant, Neon Trees and 7th Heaven. For more information, visit


Taste of Chicago: From July 8-12, Grant Park will host the annual Taste of Chicago with multiple vendors from diverse neighborhoods. Visit here for more information. Admission is free.

Roscoe Village Burger Festival: Located on Belmont between Damen and Oakley, the Burger Festival returns on July 11-12. The festival will include two stages of live music and award-winning burger vendors. Visit for more information.

Pitchfork Music Festival: Held in Union Park from July 17-19, Pitchfork boasts a strong three-day lineup of musical entertainment. For lineups, passes and more information, visit Three-day passes are sold out, but single-day passes are still available.


Photo: Adam Alexander Photography

Taste of River North: From July 17-19, The Taste of River North kicks off at Kingsbury and Erie with some of the best restaurant vendors in Chicago. Visit for more information and the lineup.

Sheffield Music Festival and Garden Walk: On July 18-19, this festival will not only have live music, but garden tours, architecture tours, food and entertainment for the kids. For more information, visit

Wicker Park Fest: The hip neighborhood festival returns July 25-26 at the corner of North and Milwaukee Avenues with live music and food. Visit for more information.

Fiesta del Sol: The largest Latino festival in the Midwest will kick off in Pilsen at 1400 W. Cermak on July 30 and run through Aug. 2. There will be live entertainment, carnival rides, food vendors, soccer games and more. Visit for more information.

Lollapalooza: The most celebrated festival of the summer returns to Grant Park July 31-Aug. 2. Paul McCartney, Metallica, Of Monsters and Men, Florence + the Machine are among the headliners. For the lineup and more information, visit


North Halsted Market Days: One of the largest outdoor events in the country for the LGBT community, Market Days takes place Aug. 8-9 on Halsted between Belmont and Addison. For more information, visit

Bucktown Arts Fest: On Aug. 29-30, the Bucktown Art Fest kicks off with a variety of arts at Holstein Park, including an open art contest. Visit for more information.


Chicago Jazz Festival: Taking place on Sept. 3-6, the Chicago Jazz Festival will have featured artists play at Millennium Park and the Chicago Cultural Center. For more information, visit here. Admission is free.

World Music Festival: The 17th Annual World Music Festival will be held Sept. 11-22 for its 11-day celebration. The venues will be scattered around the city of Chicago, so make sure to check here for updates and locations. Admission is free.

Windy City Wine Fest: Perfectly situated right at Buckingham Fountain, the Windy City Wine Fest allows you to sample some 300 wines from around the world Sept. 11-12. Buy tickets online for $35 or pay $45 at the door.