| Chicago Events | Events Venue | Events Schedule | Tickets |
| Bike To Work Day Rally | Daley Plaza and the 2009 Chicago Criterium, | June 19 | Free |
| Odyssey Champagne Dinner Cruise | Navy Pier, | June 19 | |
| 23rd Annual Scottish Festival and Highland Games | Oak Brook Polo Grounds, 700 Oak Brook Road, Oak Brook, IL | June 19, 20 | |
| Close Up 2 Smooth Jazz Festival | Federal Plaza Square 219 S Dearborn St; | June 19,4:00 pm – 10:00 pm, June 20 from 8:00 am – 9:00 pm. | !9th June Adult-$12; 20th June $17 |
| St. Josaphat Summerfest | Lincoln Park 2311 Southport, Chicago, IL 60614 | June 19 & 20th 2009 | Advance Ticket $ 10, at the gate $ 5 |
| Taste of Randolph | On Randolph Street, West of Peoria Street | June 19, 20 & 21 | |
| 1st Annual Taste of the Riverwalk | Wacker Drive & South Bank of the Chicago River from Franklin St to Lake Shore Dr | June 19,20 & 21 6a.m. – 11p.m. | |
| Treasures From The Deep | Gurnee Mills Mall, Gurnee, IL | June 19 | |
| Chicago Summerfest | Lincoln Park 2000 N Clark St | 20, 21 June 2009 | |
| Shoreline Sightseeing Fireworks Cruises | Navy Pier, 600 E. Grand 8 | 20th June | |
| Odyssey, Spirit of Chicago, and Mystic Blue Fireworks Dinner Cruises | Navy Pier | 20th June | |
| 44th annualPuerto Rican Day Parade | Columbus and Balbo Drives | 20th June | |
| Prudential Plaza Farmers Market | Prudential Plaza – Lake St & Beaubien Court | 23rd & 30th June | |
| Chicago Arabesque Festival | Daley Plaza ; | 24, 25, 26, 27 June |
