I nay be a near total novice and I do know Chi town and it’s pizza. I don’t think increasing the basil and oregano would do it for me but have you tried the fennel? Also, do you use chunky tomato sauce. Go Sox, Spring training is only a few windy days away.
Skip the sugar and buy a sweeter tomato base. Stanislaus has a “SuperDolce” sauce of some sort that purports to be extra sweet . . . I would assume that Escalon has one as well. That is likely how the pizza joints in ChiTown get the sweeter tomato flavor.
I did almost 8 months research before I came to my final sauce but the woman in Boston cranking at about 38K a week out of a litteral shack sold me. Brown sugar works! Bringing the flavors together to create a NATURAL sweet taste involves heating all your spices and ingredients slowly for a short time and to a steep followed by at least a twelve hour chill. It breaks down the acids and increases the natural sweetness of the tomato…etc.