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| Annual 26 | May 8-9 | Wojcik Conference Center | Palatine | Fan Your Journey | Stephen Yamnitz | Conner Cuneen, AS | Srinivas Saineni |
| Annual 25 | May 2-4 | Embassy Suite Schamburg | Schaumburg | Engage | Robert McKenzie & Elizabeth Stevenson | Maureen Zappala & Forrest Tuff | |
| Annual 24 | May 15-16 | Harper College Theatre | Schaumburg & Palatine | Just Connect | Jim Baloun & Stella Lorens | Verity Price | |
| Annual 23 | May 2-3 | Harper College | Schaumburg & Palatine | The Stage is Growing | | | Lark Doley |
| Annual 22 | May 15-16 | Virtual | 3rd Virtual | Explore . Dream . Discover | | | |
| Annual 21 | May 1-2 | Virtual | 2nd Virtual | Passport to Success | | | |
| Annual 20 | May 2-3 | Marriott – North Shore Glenview | 1st Virtual | Roaring Forward | | | |
| Annual 19 | May 3-5 | Schaumburg Marriott Hotel | Schaumburg | Where you are the STAR | | | |
| Spring 18 | April 20-22 | Chicago Marriott NW Hotel | Hoffman Estates | All That Glitters Is G.O.L.D. | | | |
| Fall 17 | Nov 4-5 | Chicago Marriott NW Hotel | Hoffman Estates | DAZZLE! Fantastic and Final Fall Conference | | | |
| Spring 17 | April 28-29 | Holiday Inn North Shore | Skokie | Launching A New Legacy _ R.I.S.E. – Respect, Integrity, Service, Excellence | | | |
| Fall 16 | Oct. 28-29 | Elk Grove – Holiday Inn | Elk Grove Village | Excellence = Communication + Leadership | | | |
| Spring 16 | April 29-30 | Holiday Inn North Shore | Skokie | SOAR for Success! | | | |
| Fall 15 | Nov. 7 | Countryside Banquets | Countryside | SOAR for Success! | | | |
| Spring 15 | Apr 24-25 | Holiday Inn North Shore | Skokie | S-t-r-e-t-c-h to Your Success! | | | |
| Fall 14 | Oct. 25 | Holiday Inn | Countryside | | | | |
| Spring 14 | Apr 25-26 | Holiday Inn North Shore | Skokie | Pursue Your Passion | | | |
| Fall 13 | Oct. 26 | Holiday Inn | Willowbrook | | | | |
| Spring 13 | Apr 26-27 | Holiday Inn North Shore | Skokie | The Power to Inspire | | | |
| Fall 12 | Oct. 27 | Holiday Inn | Willowbrook | The Power of Perfrormance | | | |
| Spring 12 | Apr 20-21 | Crowne Plaza – O’Hare | Rosemont | | | | |
| Fall 11 | Nov. 12 | Holiday Inn | Willowbrook | Discipline – Commitment – Persistence | | | |
| Spring 11 | May 13-14 | Holiday Inn North Shore | Skokie | Building Bridges To The Future | | | |
| Fall 10 | Nov 5-6 | Holiday Inn | Countryside | Achieving Greatness Together | | | |
| Spring 10 | May 21-22 | Holiday Inn | Elk Grove Village | Spring Forward Evolving and Growing | | | |
| Fall 09 | Nov 13-14 | Holiday Inn North Shore | Skokie | Connect, Communicate, Collaborate | | | |
| Spring 09 | Apr 24-25 | Holiday Inn | Willowbrook | Show Your Excellence: Conquer Communication & Leadership | | | |
| Fall 08 | Oct 24-25 | Holiday Inn | Elk Grove Village | Continue the Experience, Expand Your Abilities | | | |
| Spring 08 | Apr 25-26 | Holiday Inn Select | Tinley Park | Dream Builders Creating A New Tomorrow, One Toastmasters at a Time | | | |
| Fall 07 | Nov 2-3 | Westin | Lombard | Empower Yourself | | | |
| Spring 07 | Apr 27-28 | Radisson | Northbrook | Stepping Up | | | |
| Fall 06 | Nov 10-11 | Georgio’s | Orland Park | Communication is Key | | | |
| Spring 06 | May 5-6 | Sheraton Suite | Elk Grove Village | Find Your Voice, Serve the World | | | |
| Fall 05 | Nov 11-12 | Holiday Inn | Glen Ellyn | Proud To Be A Toastmaster | | | |
| Spring 05 | 4/30-5/1 | Sheraton Suite | Elk Grove Village | It’s Star Power | | | |
| Fall 04 | Nov 19-20 | Sheraton Suite | Elk Grove Village | It’s Magic | | | |
| Spring 04 | 4/30-5/1 | Holiday Inn Select | Chicago – Midway | 2004 Hear the ROAR! | | | |
| Fall 03 | Nov 7-8 | Sheraton Suite | Elk Grove Village | Explore Your Toastmasters Possibilities | | | |
| Spring 03 | Apr 25-26 | Adam’s Mark | Northbrook | Rev It Up! | | | |
| Fall 02 | Nov 15-16 | Holiday Inn | Chicago City Centre | And Away We Go | | | |
| Spring 02 | Apr 26-27 | William Tell Holdiay Inn | Countryside | Toastmasters and All That Jazz | | | |
| Fall 01 | Nov 2-3 | Holiday Inn | Oak Lawn | The Magic of Excellence | | | |
| Spring 01 | Apr 27-28 | Sheraton Suite | Elk Grove Village | 2001: A Toastmasters Odyssey | | | |
| Fall 2000 | Nov 17-18 | Holiday Inn North Shore | Skokie | Golden Memories, Golden Opportunities | | | |
| Spring 2000 | Apr 28-29 | Hyatt Lodge | Oak Brook | Surprise Yourself | | | |
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