I am going on a trip soon that starts in Chicago ends in Italy. However, I stop at Munich before I get to Italy; I have a friend that says they can pick me up when I get to Munich. What I want to know is, is there a way for me to have my luggage able to be retrieved by me when I get to Germany?
This is called short-checking and it is sometimes possible, particularly if you have an overnight connection and might need your bags' contents. For short connections, the request might be refused as some people use it for so-calle hidden-city ticketing, where they buy a cheaper ticket from A to B to C to actually travel to city B.
Note that you'll need to recheck your bag before boarding your flight to Italy, so you'll need to return to the airport within a long enough period to permit time to check the bag and clear security.