OK, Joel, I'll bite, and seeing we're both from the same neck of the woods it should be interesting, all departed destinations:
First sit-down restaurant: Mr. Ricky's (named after Rich Melman by his father), Skokie
First fast food: Bay's (donuts plus @ Howard & Lincoln)
First buffet: Obie's (Touhy/Kostner)
First Chinese: Nankin (later worked delivery at Ah Fong)
First pizza: Pinocchio's (Main/Tripp)
First drive-in w/carhops: Richard's (Lincoln Ave. near Pratt near the original Lou Malnati's)
A couple other things I remember about dining at an early age--my dad took me to a ton of Blackhawk games from the time I was young as he had season tix and my mom would rather stay home. When we would grab a quick bite it was always at Jumbo John's (later called Capizzi's) at Grand/Damen, where you'd walk in, grab a bottle of pop from the cooler and order a slice of pizza or spaghetti or mostaccioli. In and out in about 30 minutes max, I thought that was exotic, until one night I remember my dad's friend Dave wolfing down a combo with red sauce, the juice running down his arm--that was wild. He was also our 'muscle' when parking near the Stadium on one of the side streets and neighborhood boys would 'watch' our car for a price, usually fifty cents or a buck.
But I remember one memorable night--3/12/66--when we pre-gamed with a bunch of other people--I was the only kid--at Barney's Market Club (named after owner Barney Kessel--"Yes, Sir, Senator!") at Randolph/Halsted. I had steak like the others and Bobby Hull broke the 50-goal season record later that night!
Memories of sports & food, intertwined!