“Lolla” has become one of the most popular music festivals in the country, particularly since it takes place right in the midst of a big city. This year’s headliners include The Black Keys, Red Hot Chili Peppers and Black Sabbath.
Head down to Wrigleyville and soak in the Cubs-friendly atmosphere at this street festival. In addition to tons of vendors offering tasty food and refreshing drinks, some of Chicago’s favorite local bands will perform.
Northalsted Market Days
August 11-12/Halsted Street
Join in the fun in the Lakeview neighborhood during one of the most entertaining street festivals of the year. Live music is the highlight of the event, with performances from Olivia Newton John and The Pointer Sisters this year.
Chicago Air and Water Show
August 18-19/North Avenue Beach
This annual free event offers some of the greatest summer entertainment in the city. Watch as the U.S. Navy Blue Angels zip through the sky along with other aircraft groups, including some amazing parachute teams.
Chicago Dancing Festival
August 20-25/All over Chicago
See local and national dance companies put on their best performance during this annual festival. Admission is free to this celebration of dance, which takes place at multiple venues around the city.
Chicago Jazz Festival
August 30-September 2/Grant Park
Every year, this Jazz Festival is one of the top Labor Day activities in Chicago. Admission is free to this musical event, and the headliners for this year include big names like Dianne Reeves and Allen Toussaint.