In the spring of 2000 Crowley was preparing for his ninth annual Kite Nite exhibit. He also entered one of his own kites in the Chicago Artists' Coalition's Chicago Art Open exhibition, which was co-chaired by Tom Robinson. Robinson, a fine artist and master furniture maker, came up with the idea of expanding the kite show throughout many galleries simultaneously.

As the two men began to plan Kite Week, Kochanski suggested that this was the impetus they had been seeking to form a not-for-profit organization to support Chicago artists and art education. The trio formulated a vision of what could be further accomplished if they organized.
And so Windy City Arts was conceived.

Kite Week was a huge success, involving 100 kites by 60 Chicago artists shown throughout eight participating art galleries. After Kite Week the team looked for ways to broaden the outreach of the organization. The opportunity arose to get involved with the city's Suite Home Chicago event and they began inviting artists to join forces painting a couch. One of these artists was Jill Zylke, a painter and graphic designer. She then became the fourth director.

For their most recent venture, as part of Chicago Artists Month 2002, WCA brought together over 20 local artists to work on the Totem Project. Each artist created a section of the totem independently, then came together and collaborated to assemble the final totem sculptures.

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