A guzzi... fun!
Be sure you have her all prepped and perfect, ready to go. Guzzi dealers aren't real common here, especially out west. Maybe see if what support or dealer info the US guzzi owners group may offer. You don't want to be stuck in nowhere Kansas, at a Harley dealer, with the mechanic saying "well, the first thing we need to do is turn the engine the correct way"
You might want to hit the rock n roll hall of fame in Cleveland OH.
Regarding Chicago. The traffic sucks. Particulary sucky is the Illinois Toll Road, I-80 west. This is a 'stop every 5-8 miles pay toll' type toll road, if you don't have an EZpass transponder. Yes, it can be ridden, and I've done it, but... it aint' fun.
If you run thru NW Ohio, Interstate 80 / 90, stop by. I can show you the boredom that is my corner of the world. Also, I live within 7 miles of a guzzi dealer if you need one. I hope you don't!
Chicago would possibly be a good place to see a music show however- many venues. Try livenation.com for tickets at shows around the country. There are various outdoor venues around the country if you want to see a big show. If you're hitting New Orleans and Nashville, you'll definitely find plenty of music in those places.