From 1958 - 1993 UChicago’s endowment grew only 32% in real terms (ie over and above what it would have done anyway at some steady rate of return). In the same time period, its peers - defined by UChicago to be HYPS, Columbia, MIT, Penn, Cornell, and NU (no Duke for some reason though they’d probably include it now) - all experienced real endowment growth of about 157%. This analysis is in the Boyer book.
I updated that analysis using the 2018 data that Cue provided and a long term regular endowment return rate that reflects slightly lower inflation over the past 25 years. As a result, UChicago’s real growth was about 115% - a notable improvement! However, the peers grew 178% - faster than their old increase and in less time. So while UChicago has obviously picked up speed, the peers are outpacing it. Furthermore, it’s the ones with UChicago-sized endowment 25 years ago that have really done well: Penn (318% real growth); MIT (214% real growth), NU (182% real growth). Only Columbia and Cornell experienced less real growth than did UChicago. Those two schools are also smaller in endowment relative to UChicago when normalized for the actual size of the schools (measured by population).
If UChicago can get alumnae and similar giving to really kick in, it should be able to catch up to NU and Penn. But HYPS and even MIT are so far ahead of the game that I seriously doubt UChicago can ever be competitive on endowment alone. This is why they will need to continue to do more with less.
(Of course, one way to be doing more with less is avoiding that $500k/student threshold for the endowment tax. UChicago is just under. NU is just over, and by my estimates might be paying about $7 mill per year to Uncle Sam. And Harvard might be paying a cool $24 million!)