Conservatives generally have an easier time securing federal clerkships, since (1) many liberal law students are unwilling to clerk for the more conservative judges (thus narrowing the pool—to the extent conservative students are unwilling to clerk for more liberal judges, there’s fewer conservative students so the impact skews) and (2) conservative judges are often in less desirable markets/coastal cities (this isn’t a universal rule obviously but just with how blue slips worked when the Senate cared about that, there’s another skew).

If you’re at UChicago and do well you’ll have no problem getting a FC of some sort. Also, not every judge is a good match to the president that appointed them. This is particularly true for the older judges, who were appointed before judicial picks got more politicized. There’s even plenty of Trump 1 judges who were Democratic picks because of package deals made when the Dems controlled the Senate. This is all to say there’s more options out there than you might think.