October 2001 – Brian Posen comes up with the idea of SketchFest to fill a seven-week rental commitment he'd made to Theatre Building Chicago.

January 2002 – The first Chicago Sketch Comedy Festival begins. It runs for seven weeks and features more than 30 Chicago sketch comedy groups. About 2000 patrons attended.

January 2003 – The second SketchFest was shortened to 3 ½ weeks and featured 53 performing groups from Chicago and across the country. SketchFest added a panel of sketch comedy experts and weekly forums for performers to exchange ideas and information.

January 2004 – SketchFest expanded to take over all three spaces in Theatr Building Chicago and put up 120 performances by 71 groups in just two weeks. Two new events heightened the festivities – Sketchubator and OctaSketch.

January 2005 - SketchFest 2005 grew even further and became international with the addition of funny Canadians. As if performances by more than 83 groups wasn't enough, SketchFest added writing workshops featuring The Onion head writer Joe Garden and The Comic Toolbox author John Vorhaus. Chicago Sketchfest changed its official name to "The Chicago Sketch Comedy Festival." Some patrons had actually called the box office to see if it was a festival about drawing.

January 2006 - Five-year anniversary! 92 sketch comedy groups (that's more than 700 artists) came together to perform, collaborate, share information and support one another, all under the umbrella of funny and love. A rock star event called Master Sketch was added.

January 2007 - The festival was one shy of 100 groups (800 funny people performing) and hit 10,000 patrons. OctaSketch entered its 4th year, and honored The Second City, iO, Annoyance and ComedySportz by having each supply a director who created under their specific style.

January 2008 – This time, SketchFest reached 100 groups. Like past years, the festival was honored to host a mess of new groups and welcomed back some of our old friends.

January 2009 - Sub-zero weather and blizzards… still, 10,000 bodies came through our doors again! SketchFest became trans-Atlantic, hosting some lovely folks from Manchester, England. SketchFest became family friendly for a few hours, with sketch BY kids, sketch FOR kids and sketch EDUCATING kids.

January 2010 – This is the year of, "If it ain't broke, don't fix it". 100 sketch comedy troupes performed almost 150 shows in the two weekends, and SketchFest experienced record ticket sales.

May 2010 – SketchFest parent company Lukaba Productions takes over management of the Theatre Building Chicago venue where SketchFest has been for nine years! They change the name of the company and the building to Stage773.