Good idea!
There are a ridiculous amount of excellent restaurants in Chicago, something for everyone. Many folks ask me for recommendations for a good Italian place. Considering my maternal grandmother and grandfather come from Sicily I rarely eat Italian food out, but one of the best is Rosebud's. There are now several locations...but THE location to hit is the original located in the "old neighborhood" (Little Italy) on Taylor St. My dad grew up the neighborhood...thus the "old neighborhood" reference.
The food is excellent, almost as good as Grandma's!
At the end of the block where my dad grew up is one of the best stores around, Fontano's on Polk St and Carpenter. My dad and Red (the owner) were best friends, so we went there a lot! It is an "Italian store" in the front and a deli in the back. It is THE place to go for an Italian sammich that will make you want to slap your momma.
I can remember as a little girl walking in to the store and it just smelled like home. The aromas surrounded you, you could almost taste the cheeses and salami, the "gravy" cooking in the back room...ahhhh the memories! There are several suburban locations which are rather generic but the original in the "old neighborhood" is the best.
Right across the street is the best Italian Ice in the city!
Just for fun, one other thing I remember is the "chi-chi" man, an old Italian man that would come down the street every day with his cart filled with various hot nuts, pistachios, cashews etc. We'd start yelling "chi-chi" and run down the stairs of my grandma's house for our favorite treat!