Best I've had is at Pastecceria Natalina, but they are pricey at ~$6 a pop.
Best value cannoli I've had is at D'Amato's, at only $1.80 a pop.

(While the PN sfogliatelli look tasty, I have a hard time spending ~$10-11 for a fancy croissant)

Al's Beef and Luke's Beef.

Both similar styles. Better hot giardinera for Al's, but a larger sausage for the combo sandwich by Luke's. Portillo's is okay. Their meat is sliced thicker than both Al's and Luke's.

Vanille is not a typical American bakery, but a patisserie, whose main emphasis is pastry/desserts. The main reason you go there is for the entremets. If you want brownies or cookies, go elsewhere. They also happen to have the best almond croissants in Chicago.

No, just rearrange the meat/cheese within the roll once you get it.

Cheeze Whiz, Lt Onions, on garlic bread. Sprinkle a little kosher salt on top when it arrives.