This week's can't-miss pick
Chicago Bears Preseason Home Opener vs. Cleveland Browns
The Bears' first home game of the 2026 preseason — first look at the roster before final cuts.
🎟 See Bears TicketsConcerts
Concert
moe. and Umphrey's McGee
Ravinia Festival (Pavilion)
A jam-band double bill closing out Ravinia's summer pavilion run for the season.
🎟 See Ravinia Tickets
Free & Family
Free
Grant Park Music Festival — Final Weekend
Jay Pritzker Pavilion, Millennium Park, Chicago, IL
Last chance to catch this free summer series before it wraps for the season.
🎟 See Festival Schedule
How we pick these
We look for events with real drawing power — major touring acts, marquee sports dates, and long-running Chicago traditions — and skip anything too thin to be worth a special trip. Suburb events (Highland Park, Evanston, Naperville, and beyond) are included alongside the city; Chicagoland is Chicagoland.