Ciao Maura!
I hope you're looking forward to your trip coming up so soon. For entrance into Italy, you will need to show your CDC vaccination card.
Also, be sure to pack some FFP2 or KN95 masks which are required for transportation in Italy. If you can't find them in the US they are easy to track down in Italy at convenience stores or at pharmacies.
P.S. I also am from Chicago - have a safe flight :)