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2020 DATES - ALWAYS CHECK TO MAKE SURE DATES/LOCATIONS HAVEN'T CHANGED
| Day | Date | Venue | City | St. | Time | More Info | Map | Website |
| Sat | January 4 | Durty Nellies - Fan Appreciation | Palatine | IL | 9:00pm | 21 & Over | Map | Website |
| Fri | January 10 | Hollywood Casino | Aurora | IL | 10:00pm | 21 & Over | Map | Website |
| Sun | January 12 | Roy's Benefit at Woodfire Tavern | Long Grove | IL | 1:00pm | Cancer & Bookdrive Benefit | Map | Website |
| Sun | January 19 | Chicago Music Cruise | Caribbean | FL | All Day | Annual Cruise | Map | Website |
| Mon | January 20 | Chicago Music Cruise | Caribbean | FL | All Day | Annual Cruise | Map | Website |
| Fri | January 21 | Chicago Music Cruise | Caribbean | FL | All Day | Annual Cruise | Map | Website |
| Sat | January 22 | Chicago Music Cruise | Caribbean | FL | All Day | Annual Cruise | Map | Website |
| Thur | January 23 | Chicago Music Cruise | Caribbean | FL | All Day | Annual Cruise | Map | Website |
| Fri | January 24 | Chicago Music Cruise | Caribbean | FL | All Day | Annual Cruise | Map | Website |
| Sat | January 25 | Chicago Music Cruise | Caribbean | FL | All Day | Annual Cruise | Map | Website |
| Sun | January 26 | Chicago Music Cruise | Caribbean | FL | All Day | Annual Cruise | Map | Website |
| Sat | February 1 | Joe's Live | Rosemont | IL | 10:00pm | 21 & Over | Map | Website |
| Fri | February 7 | First Look Auto Show Gala | Chicago | IL | 6:00pm | Ticketed Gala | Map | Website |
| Sat | February 8 | MT Barrels | Schaumburg | IL | 10:00pm | 21 & Over | Map | Website |
| Fri | February 14 | TBA | IL | Map | Website | |||
| Sat | February 15 | Tailgaters | Bolingbrook | IL | 21 & Over | Map | Website | |
| Fri | February 21 | TBA | IL | Map | Website | |||
| Sat | February 22 | Sundance Saloon | Mundelein | IL | 21 & Over | Map | Website | |
| Fri | February 28 | Brauer House | Lombard | IL | 21 & Over | Map | Website | |
| Sat | February 29 | GiGi's Playhouse Gala | Schaumburg | IL | Ticked Gala | Map | Website | |
| Fri | March 6 | TBA | IL | Map | Website | |||
| Sat | March 7 | Base Camp | Lisle | IL | 21 & Over | Map | Website | |
| Fri | March 13 | Finn McCool's Outdoor Tent | Schaumburg | IL | Outdoor Heated Tent Fest | Map | Website | |
| Sat | March 14 | McHenry Shamrock the Fox Fest | McHenry | IL | All-Age Outdoor Festival | Map | Website | |
| Fri | March 20 | TBA | Map | Website | ||||
| Sat | March 21 | TBA | Map | Website | ||||
| Fri | March 27 | Huntley Bowl | Huntley | IL | Map | Website | ||
| Sat | March 28 | Joe's Live | Rosemont | IL | 21 & Over | Map | Website | |
| Fri | April 3 | Cabo San Lucas | Cabo | MX | Map | Website | ||
| Sat | April 4 | TBA | Map | Website | ||||
| Fri | April 10 | Hollywood Casino | Aurora | IL | 21 & Over | Map | Website | |
| Sat | April 11 | Tailgaters | Bolingbrook | IL | 21 & Over | Map | Website | |
| Fri | April 17 | HOME Bar | Arlington Hts | IL | 21 & Over | Map | Website | |
| Sat | April 18 | Catholic Charities | IL | Ticketed Gala | Map | Website | ||
| Fri | April 24 | TBA | IL | Map | Website | |||
| Sat | April 25 | Sundance Saloon | Mundelein | IL | 21 & Over | Map | Website | |
| Fri | May 1 | TBA | IL | Map | Website | |||
| Sat | May 2 | TBA | IL | Map | Website | |||
| Fri | May 8 | TBA | IL | Map | Website | |||
| Sat | May 9 | Base Camp | Lisle | IL | 21 & Over | Map | Website | |
| Fri | May 15 | Long Grove Chocolate Fest | Long Grove | IL | All-Age Outdoor Festival | Map | Website | |
| Sat | May 16 | Joe's Live | Rosemont | IL | 21 & Over | Map | Website | |
| Fri | May 22 | TBA | IL | Map | Website | |||
| Sat | May 23 | TBA | IL | Map | Website | |||
| Fri | May 29 | Taste of Glen Ellyn | Glen Ellyn | IL | All-Age Outdoor Festival | Map | Website | |
| Sat | May 30 | TBA | IL | Map | Website | |||
| Jan 3, 2021 | Chicago Music Cruise 2021 | Caribbean | FL | Annual Cruise 2021 | Map | Website |
KEY: CITP = Concert in the Park - typically a concert ran by the Park District mid-week.
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