Randolph Street Market
- 5, 19: Free! Cruise Nites | Berwyn
- 7-10: Chicago In-Water Boat Show | 31st Street Beach
- 8-9: Free! Art and Garden Street Fair | Homewood
- 8-10: Free! Chicago Blues Festival | Grant Park
- 8-9: Free! Forest Park Summer Fest | Forest Park
- 8-10: Ribfest Chicago | North Center
- 8-10: Free! Rockin’ in the Park | Rosemont
- 9-10: Andersonville Midsommarfest | Andersonville
- 9-10: Free! Printers Row Lit Fest | South Loop
- 9-10: Wells Street Art Festival | Old Town
- 11: Free! Movies in the Parks kicks off | Various parks
- 13: Free! Grant Park Music Festival kicks off | Millennium Park
- 15-16: Scottish Festival and Highland Games | Itasca
- 15-17: Festa Pasta Vino | Heart of Chicago
- 15-17: Taste of Randolph Street | West Loop
- 16-17: 6 Corners BBQ Fest | Portage Park
- 16-17: Custer’s Last Stand Festival of the Arts | Evanston
- 16-17: Pizza Fest Chicago | Uptown
- 16-17: Spring Awakening Music Festival | Soldier Field
- 21: Free! Chicago Gospel Music Festival | Millennium Park
- 22: Free! Gospel Music Festival | Chicago Cultural Center
- 22-23: Chicago Pride Fest | Boystown
- 22-24: Long Grove Strawberry Festival | Long Grove
- 23-24: Chicago Gospel Music Festival | Ellis Park
- 23-24: Chicago Summerfest | Lincoln Park
- 23-24: Fountain Square Art Festival | Evanston
- 23-24: Green Music Fest | Wicker Park
- 23-24: Randolph Street Market Festival | Near West Side
- 24: Free! Chicago Pride Parade | Boystown
- 27-July 1: Eyes to the Skies Festival | Lisle
- 29-July 1: Craft Beer Festival | Old Town
- 29-July 3: Naperville Ribfest | Naperville
- 29-30: Old St. Pat’s World’s Largest Block Party | West Loop
- 30-July 1: Free! Gold Coast Art Fair | Butler Field, Grant Park
- 30-July 1: L.A.T.E. Ride | Buckingham Fountain
- 30-July 1: Wavefront Music Festival | Montrose Beach
