The University of Chicago was generally acknowledged as an excellent school and that, plus the combination of his many visits as an undergraduate, probably helped fuel his decision. Myers remembers Bellairs saying in passing that the only other graduate school he had considered was Columbia, a choice possibly influenced by the two professors at Notre Dame that had the strongest effect on Bellairs: Joe Duffy and Frank O'Malley. Duffy attended Columbia as an undergraduate and O'Malley described its English Department to Bellairs as "a bunch of great names that you never see."

That Bellairs would be attending graduate school was almost a given. "Having an undergraduate degree in English doesn't really open many alluring doors career-wise," says Myers, who doesn't think Bellairs was especially attracted to teaching per se, "but continuing one's education with a more advanced degree in graduate school was the usual course of action and college English teaching was one of the more attractive of callings."

Myers adds that John, like all students who were not independently wealthy, would not have been able to afford graduate school without some sort of scholarship. Potential candidates didn't have to be much more than a grad student in good standing to get some kind of support, assuming the university was well enough funded. The Woodrow Wilson scholarship awarded to Bellairs at Notre Dame was slanted towards future college instructors but because universities were flooded with promising young scholars produced by the Wilson scholarship program, they had the task of finding money to support them after their first year. Bowen believes that because of this, the Wilson foundation later came up with some additional money in the form of another grant. Bellairs was the recipient of this Wilson Special Grant, awarded by University of Chicago rather than through a national competition, as well as the La Verne Noyes Fellowship, given to direct blood descendant of a United States Army or Navy World War I veteran whose military service was terminated by death or an honorable discharge (John's father, Frank, served in the first World War).

Compared to Notre Dame and the sours of South Bend, Chicago was nirvana, offering pleasures of arts and entertainment to John Bellairs in the form of museums, restaurants, book and music stores, theaters and other attractions that tend to congregate around a large university. It was a drastic change of environment and cultures, with a rather brash and rather leftist undergraduate student body that Myers describes as "searching for a cause, any cause, to rally around at the tail-end of the civil rights movement and in those relatively tranquil pre-Viet Nam days. 'They're ready to form a march on the aquarium to free the fish!' as one of John's friends sardonically put it."

Longtime friend Robert Yaple describes the large campus as being in those days a "port of missing men" for graduate students. "Students there always developed a certain reputation, regardless of the degree of normalcy they possessed. In some ways, it was a pretentious amalgam of post-Ivy Leaguer and pre-Hippie; in others, it was a triumph of laissez-faire eccentricity. I've not done any research on the subject, or scientific sampling, but I would guess that about a third eventually left with the degree they'd come for (though it often took a dozen years or more). Another third left without it, but still managed to right themselves and have decent lives (though scarcely what anyone would term 'conventional'). And the rest simply vanished."

Myers describes the campus culture as very open and liberal. "It is of course a brilliant university, with over 70 Nobel Laureates to its name, far more than any other school anywhere in the world. Because the Philosophy Department is very big on the Greek philosophers and St. Thomas Aquinas, the traditional joke about Chicago is that it's 'a Baptist university where agnostic professors teach Catholic philosophers to Jews.'"

The University of Chicago is an urban campus, clustered around the so-called Midway, a broad boulevard on the south side of the city, and downtown was only a quick ride away via the elevated train. Myers says that in his era the Midway was threatened by the burgeoning slums caused by migration from the rural south. "The areas immediately off-campus, particularly to the south, and to some extent the campus itself, were not considered safe after dark. As a result, the area had become the target of a large urban renewal project sponsored by Mayor Richard Daley. The purpose was to form diversified and integrated neighborhoods around the campus, particularly the so-called Hyde Park area to the north. The effort proved to be quite successful."