Last week I was in downtown Chicago. I had to remind myself that I was looking at Willis Tower and not Sears Tower. It was also interesting to find out that United Airlines is moving their office from Elk Grove Township to Willis Tower. leasing 45,000 sq.ft. for 2,800 workers. The company will get a $25 million subsidy from the city for the move.

Later I was peering down at Grant Park and Millennium Park from one of the high rise buildings on Monroe Street. There is no doubt that this adds another attraction to the city, an interesting architectural marvel that holds its own against other historic buildings and landmarks. But given that, the park was delayed during construction and eventually cost $450 million by the time it was completed in 2004.

These two different issues made me think: Chicago has some of the best universities in the country. The city has plenty of office space and residential neighborhoods. It has great restaurants and a stellar night life. O’Hare is one of the best connected and busiest airports. In spite of all of this, why is Chicago not a hot spot for entrepreneurship? Less than 5% of the total VC money spent nationally is invested in Chicago on a yearly basis. Compare that with Silicon Valley, a region which attracted 39% of total national venture investments during the first quarter of 2009.

Chicago has done a great job in making the city a nice place to work and live. However, it has done a very poor job for creating a ecosystem geared towards entrepreneurs and new venture creation. Here’s a thought: Imagine if the city started a venture capital fund of $450 million instead of funding Millennium Park. How about funding 450 cool start ups for $1 million each and provide Willis Tower as an incubator. These companies would provided more jobs than United Airlines does. It would keep the talent in the city and create possibilities for the next Google, Facebook, or Amazon.

Chicago is a great city that needs to think beyond bidding for the Olympics, they need to create a new vision of a high tech ecosystem and sustainable development.