I suppose this is a question for me try fielding, considering my interest in vocations and username.
I’m going to skirt it slightly, though. The thing is, I always find it difficult to answer when someone asks if something is “orthodox”. For I’m not exactly sure what it is that they are REALLY looking for, more specifically. I might recommend a priest, for instance, whom I consider “orthodox”, but if he doesn’t jive with someone’s personal preferences and requirements to be labeled as such, for whatever their reasons, then the person will be disappointed and distrustful of what I’ve offerred.
That said, there are plenty of good priests in Chicago and lots who are certainly not wildly “unorthodox”. There are quite more than a few who would clearly be considered faithful. And there are plenty who probably come closer to following every jot and tittle.
The same goes for parishes. Really, it all depends upon your personal tastes and what works for you.
The seminary system here is generally good, and it’s rectors solid, if not always as excellent as it could be in every degree.
While Mundelein (the major seminary) has it’s own personality and isn’t the kind of St. Charles Borromeo, for example, that some who want “orthodoxy” would prefer, it is said to be slowly but surely changing in a positive direction from it’s more challenged history of recent times.
St. Joe’s (college seminary) is a respectable institution generally spoken well of by it’s student seminarians. It has a partnership with Loyola University, on whose campus it resides and from which the students receive their diplomas after four years of study there.
Quigley (high school seminary) does a fine job and has been doing all the better in recent years, but is closing at the end of this academic semester.
There are several other preparatory seminary programs.
Chicago is also the home of the Catholic Theogical Union. Though not associated formally with the Archdiocese of Chicago’s seminaries, numerous men (particularly from various religious orders) study there in preparation for the priesthood. It is typically considered more liberal in perspective.