Events · Chicago & Suburbs · August 2026
Your Weekend Guide to Chicago & the Suburbs —
August 21–23, 2026
Get set for a weekend packed with diverse activities across Chicago and its suburbs! From cultural festivals to exciting outdoor events, there's something for everyone to enjoy.
Check out the exciting events happening this weekend!
The R&B Tour
The R&B Tour starring Usher Raymond and Chris Brown is coming to Soldier Field on August 21 & 22!
West Loop Art Fest
Experience one of Chicago’s best neighborhood festivals at the West Loop Art Fest, a vibrant two-day celebration of art, creativity, culture, and community in the heart of the West Loop. This annual event transforms Fulton Street into a lively open-air art experience spanning four city blocks in one of Chicago’s most energetic and creative neighborhoods.
Thirsty Ears Festival
ACM’s Thirsty Ears Festival is Chicago’s only classical music street festival! Featuring stellar ensembles and soloists a huge range of classical music from all eras on the main stage.
Chicago Triathlon
World-class athletes from around the globe descend on Chicago for one of the most prestigious triathlons in the country, which includes an open-water swim in Lake Michigan.
Kacey Musgraves
Kacey Musgraves is kicking off the Middle of Nowhere Tour, with special guest Midland, at United Center on August 21st! Over the course of her career, Kacey Musgraves has earned eight Grammy Awards, including Album of the Year for Golden Hour. She has been recognized by Time as one of its “Women of the Year”, celebrated by Billboard’s “Women in Music” and Variety’s “Power of Women”, and was the recipient of the Songwriter Icon Award by the National Music Publishers’ Association.
The Lawndale Route 66 Festival
Originally rooted in the Chicago’s Historic Route 66 Classic Car Show, this free all-day festival brings together local culture, heritage, cars, music, and community pride. It honors the legacy of Route 66 while supporting neighborhood unity, youth engagement, and small business visibility.
Glen Ellyn Carnival
The Glen Ellyn Chamber is happy to announce that we will be hosting the 2026 Glen Ellyn Carnival at the Crescent/Glenwood Lot located at 505 Crescent Blvd in downtown Glen Ellyn. The carnival features over 10 various rides, a Fun House, Games & Concessions.
Heirloom Fest
Enjoy live music in a relaxed outdoor setting with friends, neighbors, and the community.
Evanston Art & Big Fork Festival
Join fellow art lovers in browsing thousands of original pieces from an impressive 150 juried artists showing paintings, sculpture, jewelry, mixed media, photography and so much more. Take a break at the extensive tasty foods area, have a personalized poem written for you, or visit the Kids Art Zone with the little artist in your life.
Huntley's 175th Celebration & Corn Boil
Celebrate Huntley’s 175th Anniversary at the Huntley Farmers Market with a morning of family-friendly fun, including live music, face painting, kids’ crafts, yard games, anniversary cake, and a free corn boil. Plus, shop fresh produce and handmade goods from local vendors and visit the Shops on Main starting at 10am.
West Chicago Food Festival
Celebrate local breweries and beer’s rich railroad history at this adults-only beer festival. Sample brews from a variety of breweries, enjoy bites from local food trucks and live music, and explore the museum while electric, steam, and diesel trains operate throughout the event.
A Great Moment in Vinyl Tribute
Great Moments in Vinyl celebrates the music of Genesis, Phil Collins, and Peter Gabriel, tracing their journey from progressive rock pioneers to some of the most successful artists of the ’80s. Enjoy the songs that defined their careers along with the stories and insights behind the music.
Allie Payne Group at Compass
Enjoy Your Weekend —
And If Home Is on Your Mind, Let's Talk.
Whether you're exploring a new neighborhood this weekend or thinking about what comes next, we're always here to help you navigate it.
