The Chicago area has long been a hub of manufacturing and finance as well as a traditional headquarters location for many Midwest corporations. Times have changed, and while Chicago still has a bustling economy, its unemployment rate hit nearly 12% this past summer due in large part to the effects of the massive layoffs in the manufacturing and transportation sector. The news has been pretty bad for the past couple of years as more and more large corporations downsize or move out of the Chicago area.
There are still a few glimmers of hope though for the Chicago area. The unemployment rate has been falling since late summer and companies like Boeing and Kraft Foods, Quaker, and Sears. All of these companies in one way or another have helped to keep the economic and unemployment bleeding to a minimum over the past 24 months, but each of these companies has been cutting jobs in many of their retail outlets, production facilities, and administrative facilities over the same period. 
The Chicago area has been a hotbed for unemployment in recent times with rates as high as 9% in non-recession years. Much of this unemployment can be attributed to the dot com failures of 1999 and 2000 and the technology bust that soon followed. Consumers do not want to spend as much money and companies are hurting, so everything from the publishing and printing business to the transportation and services sector are hurting.
The education and education-related services sectors have been remarkably robust in recent months. It seems, like many other cities that Chicago is able to keep their universities and colleges part of their economic heart. These institutions are known for their ability to escape much of the negative effects of recessions due to the fact that education is nearly always in high demand. Education employment sectors have only seen minimal cuts in jobs recently as compared to other sectors like manufacturing and transportation.
The government sector has also seen better days in Chicago, but it has been nowhere near as damaged as other sectors by the recession. Our current President Obama, hailing from the Chicago area has helped to bolster some new forms of tourism and has helped to attract new attention to the windy city, but sadly, just like the rest of the US, Chicago is straining under the pressure of the global economic slowdown.
I would expect that Chicago would not be a very hospitable place for someone to try and look for employment in. There are plenty of other locations around the country that would be able to offer a much more rich employment environment. Chicago has not been able to diversify its economy in recent years like many other US cities have been able to, and this has hurt its economy, especially in the current conditions. Chicago will likely lag behind most other major US cities and manufacturing hubs when it comes to new job and wealth creation. This even after the recession ends. Diversification and the ability to attract new and healthy businesses of all shapes and sizes have eluded Chicago in the past couple of decades.

