Sicilia Bakery at 5939 West Lawrence has the BEST cannoli’s anywhere. They make them still by hand and are the freshest anywhere. Definitely something everyone should try. If you are a cannoli connoisseur I guarantee these will be the best you ever have.
Tony's Italian Deli 6708 N Northwest Hwy, Chicago, IL - (773) 631-0055 This is a gem in Edison Park. I have eaten (and mostly disliked) cannoli all over the world. Theirs is good!
----- Tony's Italian Deli 6708 N Northwest Hwy, Chicago, IL 60631
Pasticceria Natalina in Andersonville (5400 block of north Clark) hands down. I've eaten a lot of canolli in Italy and these compare to the real thing. They also make sfogliatelle, which are ridiculously good.
Hands down, you're going to find the best canolli at Sicilia Bakery. And get a few pieces of their homemade pizza for the ride home. Bet you'll eat it cold.
I second the rec for Sicilia. Don't forget to get an assortment of cookies while you are there. Or even better a canolli cake to go along with your canolli's.
While I don't live in Chicago, a special friend does and he says he would drive out of his way for cannoli from "Original" Ferrara Bakery, Inc. on Taylor St. in Italian town.
Their website says they've been around since 1908.