Happy Wednesday!
Get ready for a weekend filled with festivals, live music, art, food, sports, and community events across Chicago and its suburbs. From the Englewood Jazz Festival and Riot Fest to Oktoberfest celebrations, local art fairs, and family-friendly activities, there’s something for everyone to enjoy.
Check out the exciting events happening this weekend!
Englewood Jazz Festival
For more than 25 years, the Englewood Jazz Festival has delivered free, live music that highlights the long legacy of jazz on Chicago’s South Side and beyond.
Riot Fest
One of Chicago’s most anticipated annual music festivals returns to Douglass Park with a powerhouse lineup featuring Twenty One Pilots, Iggy Pop, Morrissey, Alanis Morissette, and many more across multiple stages. The festival also features carnival rides, art installations, and a full schedule of after-shows.
Old Town Oktoberfest
The charming streets of Old Town come alive with the sights, sounds, and flavors of Bavaria at this Oktoberfest celebration. Expect steins of German beer, bratwurst and schnitzel, traditional folk music, and lively stein-holding contests.
Retro on Roscoe
A tradition for more than 30 years, this Roscoe Village throwback extravaganza is packed with live music, a classic car show, vintage shopping, and old-school fun for all ages.
Chicago Live!
Navy Pier transforms into a vibrant stage for Chicago’s cultural community at this free performing arts festival representing music, dance, theatre, and more. The event will feature performances from more than 100 artists and groups, all open to the public.
Chicago River Swim
Now in its second year, the Chicago River Swim is already becoming one of the city’s most talked-about fall traditions. Spectators can cheer on swimmers along the Chicago Riverwalk from Lake Street to State Street.
Riverwalk Fine Art Fair
The 41st Annual Riverwalk Fine Art Fair in Downtown Naperville features over 100 juried artists, original works of art, and free public admission.
2026 Gather 5K
Help raise funds to build an all-inclusive intergenerational Swiss Family Robinson Adventure Playground in Spring Grove. The playground will exceed what the ADA recommends for people with disabilities, both seen and unseen.
Heritage Fest
Explore the cultural diversity within the community and enjoy a variety of exhibits, demonstrations, and live performances. The event is presented by the AH Park District, AH Memorial Library, AH Historical Museum, and the Village of Arlington Heights.
Oktoberfest At The Garden
Oktoberfest at the Garden is a family-friendly celebration of the final weekend of Shimmering Summer, featuring traditional German fare, Oktoberfest beers, family-friendly activities, and live music.
Moon Festival
Dating back thousands of years, the Moon Festival, also known as the Mid-Autumn Festival, celebrates the harvest season, filling the hearts of people across Asian countries with harmony, thanksgiving, and heartfelt prayers.
Northwestern vs Colorado
The Northwestern Wildcats host the Colorado Buffaloes. The Wildcats offer some of the best Division 1 college sports action in the Midwest, featuring 12 teams competing in the Big Ten Conference.
Allie Payne Group at Compass
Your Weekend, Your Neighborhood
Whether you're exploring a new neighborhood this weekend or thinking about what comes next, we're always here to help you navigate it.
