Events in Chicago in August 2026
Chicago has 12 sourced events in August 2026. Compare dates, venues, and ticket sources below, then build the rest of your trip around the events you choose.
The Chicago calendar for August 2026 leads with these:
- Taste of AndersonvilleAug 12Source: festival calendar
- U.S. Apple Association Outlook 2026Aug 19 - Aug 21Source: festival calendar
- Lakeview Taco FestAug 21 - Aug 23Source: festival calendar
By TripSapien · Updated September 3, 2026
Sourced events
- Aug 24
- Aug 24
- Aug 25
- Aug 25
Outlaw Music Festival with Willie Nelson & Family, The Avett Brothers, Sheryl Crow and more
Huntington Bank Pavilion at Northerly Island. concert.
Source: SeatGeek
- Aug 25
- Aug 25
- Aug 25
- Aug 26
- Aug 26
Going to Chicago in August?
Add your dates and we'll build the rest of your trip around these events — every place checked for closures and booking needs.
Planning leads
Early leads on events still lining up. Exact dates and details firm up closer to your trip.
- Aug 14 - Aug 16
Chicago Jazz Festival
Annual festival celebrating jazz music with performances by local and international artists in Millennium Park and other venues around Chicago.
Planning lead · details firm up closer in · Source: festival research
- Aug 15 - Aug 16
Chicago Air and Water Show
One of the largest free air and water shows in the United States featuring military and civilian aerial demonstrations along the Lake Michigan lakefront.
Planning lead · details firm up closer in · Source: festival research
- Aug 21 - Aug 23
Chicago Gospel Music Festival
A celebration of gospel music with performances by renowned gospel choirs and artists at various venues in Chicago.
Planning lead · details firm up closer in · Source: festival research
Ready to plan Chicago?
Turn these August events into a full Chicago plan, every place checked for closures, limited hours, and booking needs on your dates.