Events · Chicago & Suburbs · August 2026
Your Weekend Guide to Chicago & the Suburbs —
August 14–16, 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!
Glenwood Avenue Arts Festival
The much-anticipated annual tradition in the Rogers Park neighborhood showcases the work of over 130 artists and more than two dozen music and dance performances in its 25th Anniversary year, as well as live arts demonstrations, kids’ activities area, and open studios.
Taylor Street Little Italy Fest
Celebrate Italian culture and Chicago’s historic Little Italy at Festa Italiana on Taylor Street. Enjoy authentic Italian cuisine, live entertainment, local vendors, and cultural attractions throughout the weekend.
Air and Water Show
The Chicago Air and Water Show presented by the City of Chicago is the largest free show of its kind in the United States. The show can be viewed along the lakefront from Fullerton to Oak Street, with North Avenue Beach as the focal point.
Bears vs Browns
NFL season is almost back! Come cheer on the Bears as they take on the Browns during this pre-season game.
Choose Chicago Neighborhood PopUp Series
Join the Chicago Greeter Neighborhood PopUp Series for free guided walks through the city’s vibrant neighborhoods – led by friendly local volunteers! Come explore, connect, and experience Chicago like a local!
Wine and Art Walk
Visit The Morton Arboretum to sip wine, take in gorgeous summertime views of Meadow Lake, and browse nature-themed artworks. The Wine and Art Walk juried art show features photography, woodturning, jewelry, painting, ceramics, fused glass, fiber arts, and more artworks created by more than 50 artists in the Midwest and beyond.
Music on Maple Street
Enjoy live music in a relaxed outdoor setting with friends, neighbors, and the community.
Annual Car Show
Explore a wide variety of classic, custom, and modern vehicles, enjoy friendly competition across 13 judged classes, and see which standout vehicle earns the prestigious Mayor's Choice Award.
Party On The Green
Bring your family and join us for a fun and festive day full of live music, bouncy houses, face painting, crafts, games and giveaways at Village Green Park! Enjoy live music in the park beginning at 4:15pm with Totally Taylor. Then, Duke Tumatoe takes the stage 5:45pm. The party will conclude with a movie-in-the-park viewing of a family-friendly movie—“Honey, I Shrunk the Kids”—at dusk. Bring your own food and blanket or lawn chairs.
Hops Aboard
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.
Summer Breeze Concert Series
Dust off your lawn chairs and get ready to enjoy great music under the stars! Concertgoers are also welcome to bring blankets and picnic dinners. Don't forget to check out our Young Artists Concessions booth for showtime snacks - and the Al Larson Cultural Center Foundation Bar, offering beer, wine, and soft drinks for sale.
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.
