Tracie, go to the library tomorrow morning and get an armload of travel books and videos. Rick Steves is a good intro for those who have no idea what's over there, but, anything will help more than people throwing random suggestions at you. You need to narrow down your search by something, be it a country or theme of interest such as food, wine, art, hiking, language, architecture, shopping, a certain kind of scenery that you like, whatever.

You have enough time that you don't need to stay in one place the whole time unless you want to. So, remember to consider open jaw itineraries. You can get a lot of places in Europe nonstop from Chicago but if your trip is this summer, it is late to book: you may spend almost half of your budget on airfare.

/pbz
PS: Italy is great for starters but there is a lot to it. Will you focus just on Italy, if so, pick a part or parts to focus on. If you will visit another country, think about what countries are reasonably close and how you would travel between them. Trains may be a valuable tool for you.