What's the best old school pizza on the South Side? That's an easy one for dedicated players of the Chicago foodie home game—Vito & Nick's at 84th and Pulaski is the one that's been anointed by general consensus for hitting all the bases (fat chunks of fennely sausage on a cracker-thin crust, old time tavern atmosphere, waitresses that call you hon, existing in a time warp where fresh basil has yet to be discovered).
Now here's a question: what's the second best old school pizza on the South Side?
Tougher to think of one, isn't it? People who grew up there might come up with candidates—Villa Nova in Stickney, Aurelio's in various burbs, etc.—but it's a pretty steep falloff from the fame that got Vito & Nick's onto Diners, Drive-Ins and Dives to the very modest regional awareness of these others. So let me suggest a candidate, not so far away that you couldn't try it after, say, a Sox game or on the way back from Midway: Pizza Castle in Gage Park.
Pizza maven Dan Zemans and I found it on a South Side pizza recon a while back. From the street the profusion of strip mall signage made it look more like a going out of business sale than a venerable pizza joint, but we soon learned that owner Rich Jensen and his crew are the kind of guys who run the kind of place that does everything right.
They knead the dough in the back (instead of buying premade crusts), they grind and mix their own sausage (instead of buying it on the cheap from El Cheapo Finest Meats), they bake in the legendary oven of old time Chicago pizza joints, a Faulds rotary oven (no longer made, savvy pizza guys keep an eye out for spare ones to cannibalize for parts). The result is a classic Chicago thin crust—crispy crust with a just-shy-of-burnt taste, bright fennel-y sausage, good enough mozzarella.
The place was started in the 70s by Jensen's parents, and is probably about the last thing left to suggest that there was once a Danish enclave in this part of the South Side. Now the area is mostly Hispanic, and every Halloween the neighborhood kids line up in their Ninja Turtle costumes for a free square of pizza. As in, kids in costume lined up for three blocks, well into the night. The neighborhood's changed, but it still knows good pizza and good neighbors.