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Chicago Festivals Are Back: A Planning Guide for Summer 2021

Image: Gold Coast Art Fair/Amdur Productions
Image: Gold Coast Art Fair/Amdur Productions

Festivals are back in summer 2021, and Chicagoans will never take them for granted again. With the city and state’s reopening timeline, festival season has gotten off to a slightly delayed start. You’ll notice an unusual concentration of events towards the end of summer and into the fall. Here’s a (by no means exhaustive) weekend-by-weekend guide to the current event calendar. 

For the sake of brevity, only day or weekend-specific events are listed here, as opposed to ongoing summer events such as the Millenium Park concert series. As many events have moved dates or venues and continue to organize rapidly, make sure to check event websites regularly.


Image: Taste of Lincoln Ave/Enjoy Illinois

Approaching its 30th year, the African/Caribbean International Festival of Life returns to Washington Park July 2-4. Final details are yet to come but in past years, this event has seen over 50,000 patrons, 200 exhibitors and 70 performing acts across reggae, caribbean R&B, pop, blues, and more.

The ever-growing Windy City Smokeout will have the United Center’s parking lots rocking with country music, plentiful beer, and fine BBQ between July 8-11. Each night’s headliner is Brett Eldredge, Darius Rucker, Dierks Bentley, and Jon Pardi, respectively. This weekend will also host the two-day, free admission Southport Art Fest.

Late July starts a very busy time for neighborhood festival lovers. Kick things off on Thursday, July 15th with Rogers Park’s Taco Crawl. That weekend, July 16-18, will see the Millenium Art Festival in the Loop (free admission), the Belmont-Sheffield Music Fest in Lakeview, the Chinatown Summer Fair, and a summer newcomer: the delayed Chicago Auto Show.

The following weekend of July 23-25, find Wicker Park Fest and the  Taste of Lincoln Avenue in Lincoln Park.

Lollapalooza will be back in Grant Park between July 29-August 1. Top headliners include Miley Cyrus, Foo Fighters, Tyler the Creator, Post Malone, Journey, Megan Thee Stallion, and Steve Aoki. That weekend will also see Jefferson Park’s Jeff Fest.


Northalsted Market Days, taking place August 6-8 on Halsted St between Belmont and Addison,  claims to be the largest street festival in the Midwest. It typically boasts five live music stages and over 250 vendors of all kinds. In the middle of that weekend, take a detour over to the Old Irving Park Beer and BBQ Challenge on Saturday, August 7, where you get to judge the best beer and barbecue pairings. Or head down to the Printer’s Row Art Fest August 7-8.

August 13-15 is another heavy-hitting weekend. The Wells Street Art Festival, which normally occurs in June along with the Old Town Art Fair, will have Old Town all to itself this time. Meanwhile you’ll have the Little Italy Festa on Taylor St, Edison Park Fest, and a rarity: Chicago’s only classical music festival, Thirsty Ears Festival in Ravenswood. Also, a “Generation X haven” in Roscoe Village, where you’ll find the Retro on Roscoe festival for those looking for a blast from the past. But who could forget the Bud Billiken Parade in Bronzeville, the largest African-American parade in the United States.

On Thursday, August 19, the USO of Illinois’ annual block party, Clark After Dark, will take over a River North block with food, drinks, and live music. The August 20-22 weekend will feature The Lyrical Lemonade Summer Smash at Douglass Park, which hosts a long list of up-and-comers in rap. The headliners for each day are A$AP Rocky, Lil Baby, and Lil Uzi Vert, respectively. In nearby Union Park will be Ruido Fest, a three-day Latin Alternative festival. Meanwhile, Rogers Park’s Glenwood Ave Arts Fest, Humboldt Park’s Sangria Festival, and the Gold Coast Art Fair in Grant Park will take place this same weekend.

On the final weekend of the month on August 27-29, make sure to check out the Taste of Greektown.


Image: Riot Fest/Riot Fest


On Labor Day weekend, head out to Roscoe Village on September 4-5 to try at least a dozen burgers. It’s the Roscoe Village Burger Fest, with just a $10 suggestion donation to get in.

Pitchfork Music Festival at Union Park headlines the September 10-12 weekend with its own headliners of Phoebe Bridgers (Friday), St. Vincent (Saturday), and Erykah Badu (Sunday). Also taking place that weekend will be Lincoln Square Greek Fest and the Printer’s Row Lit Fest.

Riot Fest follows the next weekend, with headliners including The Smashing Pumpkins, Lupe Fiasco, Run the Jewels, Dropkick Murphys, Nine Inch Nails, and Machine Gun Kelly taking Douglass Park between September 17-19. If looking for one last art fix before the end of festival season, head to Artfest Michigan Avenue happening this weekend as well.

Festival season will surely go out with a bang as the Chicago Pride Parade has been rescheduled for October 3. That weekend will also feature EDM festival Spring Awakening at Addams/Medill Park, “outdoor chicken wing block party” WingOut Chicago in Old Town, and Chicago Wine Fest at the Lincoln Park Zoo.