Chicago events are back in a big way for the summer of 2021. What are the best things to do in Chicago this summer? From neighborhood bashes to Lollapalooza and even the Chicago Auto Show, these 15 Chicago summer events are not to be missed.
Looking to add a little culture to your week? Catch some rays on the lovely Anne and John Kern Terrace Garden at the Museum of Contemporary Art for free music from the city’s internationally renowned jazz community. Musicians and groups like Chuck Webb’s Guru Tonic, Twin Talk, Maggie Brown and more will be playing all summer long; beverages and light bites are available on the upper terrace. Through August 31, 220 E. Chicago Ave.
Pride in the Park
What better way to celebrate Pride Month than with a bash in Grant Park? Returning to the city for a second year after its successful 2019 debut, Pride in the Park features big-name musical artists Chaka Khan, Tiesto, and Betty Who, drag stars Alyssa Edwards and The Vixen, and a variety of other entertainers. A portion of ticket sales benefits The Center on Halsted, the Midwest’s most comprehensive LGBTQ community center. June 26-27, 280 S. Columbus Drive.
For a more classical take (literally) on summer music festivals, head to Pritzker Pavilion for the Grant Park Music Festival. With artistic director and principal conductor Carlos Kalmar at the podium, the festival will feature the Grant Park Orchestra and Chorus performing fan favorites like the Grieg Piano Concerto, the New World Symphony and the William Tell Overture. July 2-21, Millennium Park
With eight stages and more than 170 bands from across the world, Lollapalooza—now in its 16th year in Chicago—is one of the world’s most epic music festivals. Headliners this year include Miley Cyrus, Journey and the Foo Fighters; other acts to catch include Modest Mouse, Jack Harlow, Dominic Fike, Surfaces with Goth Babe, the Peach Tree Rascals and more. July 29-August 1, 337 E. Randolph St.
A summer-perfect combo of beer, barbecue and country, Windy City Smokeout showcases top pitmasters from across the nation—from Blue Oak BBQ in New Orleans to Rodney Scott’s BBQ in Birmingham—who will be practicing their craft alongside local faves like Bub City and Green Street Smoked Meats. On stage, headlininging country stars John Pardi and Brett Eldredge will keep things swinging, with additional appearances from Darius Rucker, Dierks Bentley and Morgan Evans. July 8-11, 1901 W. Madison St.
Southport Art Fest
The historic Southport Corridor comes to life for this festival featuring a striking assortment of fine art including acrylic, sculpture, watercolor, jewelry, metal, glass and more from a variety of talented Chicago artists. With games and activities for little ones, this is one of the neighborhood’s most family-friendly summer events. July 10-11, 3701 N. Southport Ave.
Now here’s a summer treat: Traditionally held in February, the Chicago Auto Show has moved to summer for 2021. The oldest auto show in North America, the iconic event is now in its 120th year; this special edition of the iconic event moves to the West Building of the McCormick Place complex, and the rest will expand into the outdoors taking advantage of the summer weather. From the latest in EV technology to the hottest luxury cars (think the 2020 Maserati Ghibli and 2020 Rolls-Royce Phantom), this event is a must for Midwestern auto enthusiasts. With the show's move, attendees will have the opportunity for more test drives, test tracks and technology demonstrations taking place alongside Indiana Avenue and special experiences with the new Ford Bronco. July 15-19, 2301 S. King Drive
Belmont-Sheffield Music Fest
One of the North Side’s most beloved summer fests, this 36th annual bash is a celebration of local talent, eats, libations and artisans, all in the heart of Lakeview at the bustling intersection of Belmont and Sheffield. Music from top tribute bands like Hello Weekend, Breakfast Club and Rod Tuffcurls & The Bench Press adds to the appeal. July 17-18, 3200 N. Sheffield Ave.
This newcomer to the city's summer festival scene is an art collector's dream, offering a variety of works at all price points in a range of styles and media. Set in the South Loop's picturesque Printers Row district, the event also features food and drink offerings from neighborhood favorites 3rd Coast Cafe, La Storia and Beatrix. August 7-8, 701 S. Dearborn St.
A celebration of all things Italy, this four-day street festival showcases some of the city’s best food from Little Italy’s top restaurants like Rosebud, Pompei and Tuscany Taylor. Patrons can also shop a selection of Italian goods, from ingredients for cooking to fine art and more. Stick around to taste some samples from the first Gelato Festival Chicago, which offers all-you-can-eat Italian desserts that are made on site. August 12-15, 1431 W. Taylor St.
Gold Coast Art Fair at Grant Park
Celebrating its 64th year, this downtown festival is a showcase for 200 notable artists from across the country. Festival attendees can browse shoppable art, check out artist demonstrations and enjoy a variety of food and drink from local vendors. Feeling philanthropic? You can make art donations through The Chicago Furniture Bank. August 21-22, S. Lakeshore Drive & E. Monroe St.
Roscoe Village Burger Fest
Calling all carnivores: Billed as “The Midwest’s ultimate backyard grill out,” this 14th annual event features more than a dozen of Chicago’s top burger eateries. Also on tap: two stages of live music plus kids’ entertainment and more. Capping off the weekend, a popular vote will crown one winning restaurant with the title of Chicago’s Best Burger. September 4-5, 2000 W. Belmont Ave.
Lincoln Park Greek Fest
Experience the concept of filoxenia and the hospitality of Greek culture at this annual event benefiting St. George Greek Orthodox Church. Guests can take a culinary tour of Greece with offerings like gyros, souvlaki plates, moussaka, spanakopita and a variety of other traditional favorites and enjoy live entertainment from Chicago festival favorite 16 Candles. September 10-12, 2701 N. Sheffield Ave.
Riot Fest
This three-day Douglas Park event is a dream weekend for rock and punk fans, with a lineup that includes veteran acts like the Dropkick Murphys and Smashing Pumpkins and current stars like Machine Gun Kelly. Take your experience to the next level with the three-day Ultimate pass ($1600), which includes access to a 25-person cabana with an elevated view of the stage, personal concierge service and an all-inclusive private bar with a bartender. September 16-18, 2850 W. 24th Blvd.
Photography by: Grant Park Music Festival; © MCA Chicago; Windy City Smokeout
