Tupac4, if quirkiness and intellectualism are what you’re after, you might look into St. John’s College. There’s one campus in Annapolis MD and another in Santa Fe.
From what I hear it has a strong common core focused on liberal arts (IIRC modeled on what the core was like at Chicago in earlier days) and if anything, seems even more quirky and intellectual than Chicago. And it has a much higher admission rate than Chicago, something on the order of 80%.
The St. John’s core curriculum is unique. As I understand it, everyone studies in practical lockstep for most of their college careers; there are limited opportunities the last two years for elective focus in one or another field. They start with the Greeks and move chronologically through the history of ideas – philosophy, math, science, literature – studying everything from primary sources as it developed. So, for example, they study geometry by reading Euclid, and calculus by reading Leibniz and Newton. They replicate the development of Western civilization over the course of four years. It is the most extreme version available of a “Great Books” curriculum.
The Chicago core was never like that. Even in its earliest manifestations, it stood somewhat in opposition to the Great Books approach. There was some tugging in that direction along the way, but I think that the Chicago approach has always valued quality of critical thought over a comprehensive reading list.
That said, of course St. John’s attracts students who might also be attracted to the University of Chicago.
Would offer Williams as a place that (I don’t think) has been mentioned yet. Chicago and Yale have a lot in common–for example, WR Harper, Chicago’s founding president, was recruited from Yale, and James Angell (whom the trustees wouldn’t elevate to the presidency at Chicago because he wasn’t of Baptist faith), eventually went on to be the Yale president who built the core of the housing system that may be Yale College’s most distinctive feature. Columbia gets mentioned along with Chicago, but I don’t quite get it–think it has more to do with the fact that they are lumped in as the high SAT/non-tech schools that finish just outside the money in the HYPS sweepstakes. As for St. John’s, the comparison gets made, but I think it’s inapt. In the Hutchins era at Chicago (regarded as the UofC’s golden age by many), the faculty specifically rejected the “Great Books” curriculum that Mortimer Adler advocated, and which Hutchins approved of. The Chicago core, which lives on in some form today, is informed by the Great Books, but is definitely not based on them.
That, and it’s the other such university that (a) has a compulsory core curriculum for all non-engineering students that accounts for about a quarter of the credits required to graduate, and ensures that all freshmen have huge overlaps in what they are studying and all upperclass students and alumni have a strong common frame of reference, (b) is located in the middle of a megacity, (c) has significant strength in graduate and professional programs, and (d) does not have significant strength in athletics. That’s a lot of important similarity.
I agree, there are plenty of more subtle, but no less important differences, too. I completely understand why you suggest Williams; I think its intellectual tone is very close to Chicago’s, even if every other thing about it is utterly different. (My Chicago-loving kids used “Williams” as shorthand for “Don’t even suggest I look at it.”) But it’s a little silly to deny that Chicago and Columbia are going to appeal to lots of the same applicants, in a way that, say, Brown or Duke (or Williams) don’t. Unfortunately, it doesn’t help high school seniors very much to suggest they apply to Columbia in case they don’t get into Chicago. And Williams isn’t much better as a backup.
How about Washington University in St. Louis? I know there are some important differences from Chicago - such as, Wash U has undergraduate business and engineering - but my sense is that historically anyway there has been considerable overlap in the applicant pools, both are moderate sized private schools in large midwestern cities, both have some prominent graduate programs, etc.
And not to say that Wash U is a safety school by any stretch of the imagination, but the admission rate is roughly double that at Chicago.
@JHS, thank you for your points, which are well-taken–although I have strong feelings that Chicago and Columbia are far different than the objective similarities suggest. Regardless, my mention of Columbia (and Williams) were unresponsive to the OP’s request to address interesting/urban/less selective. On that (and repeating some of the good advice already provided), I’d offer the following list, which is roughly in perceived selectivity order, from more to less: Brown, Johns Hopkins, WUSTL, Carleton, Berkeley, Occidental, Rhodes, and Reed. Somewhere on that continuum, my view is that one could have a very interesting college experience that’s a standard deviation or so away from the mean.