TexasCHLforum.com

The problem is you are traveling to Chicago and stopping. That nullifies the traveling exemption. I would suggest you contact a gun store in the Chicago area and see if they can offer a suggestion on how most people travel into the state and Chicago in particular. There is also the state site here http://www.isp.state.il.us/foid/firearmsfaq.cfm" onclick="window.open(this.href);return false; that answers some questions, but Chicago in general has the prohibition on firearms that you need to address. You might also contact the Illinois State Rifle Association http://www.isra.org/" onclick="window.open(this.href);return false; and see what they can tell you.

EDIT TO ADD: I would not 'check' my gun with any law enforcement agency. They won;t usually do something like that. However, if you can't travel into Chicago, you may want to check it with a gun store/gunsmith outside of the Chicago area that is friendly and willing to hold it.