If baked at 350 degrees for 15 minutes the thin crust leftovers are very good and the crust wlll be crispy. The deep dish or thick crust is a much tougher animal to reheat and then capture the original glory of the pizza. As I said I am not a fan of Chicago style and have always eaten and worked in restaurants that made the thin crust variety which is far more popular here.
The main advantage of Chicago style is you can heap more cheese and sauce and toppings on the pie while maintaining its structural integrity. This is harder to do with a thin crust pie that is heavily topped. It’s a very significant skill to learn how to cook a thin crust pie topped with fresh mushrooms, which let out a large amount of water when baked on high heat. The Chicago style Chefs are using deep dishes in many cases that enable drainage; no such cheats are available to the thin crust chef, who must rely on knowledge of oven heat, types of ovens etc. to modify preparation of such pies. Thin crust pizza is culinary artistry, whereas Chicago is a bastardization of the cuisine in the same way as quiche is to more traditional puff pastry entrees.
I hate to say Titilleur but if you visit New Haven and walk in to Pepe’s or Modern Pizza and ask for Chicago style
you will likely be asked to leave more quickly than if you ask for smoked meat instead of Pastrami at Katz’s. Katz will hook you up with smoked meat (possibly); you have no chance of getting Chicago style at Pepe’s, Modern, Sally but their pizza is the best and much better than any flatbreads you have in Montreal.
Montreal does have us beat on bagels and crepes though. The best!