I vote St. Louis-as another poster mentioned, we were referred to as “Rome of the west”. Plus, now, we have Archbishop Raymond Burke: Need I say more.
And, I guess if you’re in the city, the Church is shrinking, but I’m one of those horrible “white flighters” who moved to St. Charles County, and Catholicisim IS booming out here. Like AgapeWolf mentioned, youth ministry is very vibrant, and my parish (Immaculate Conception) has The Dead Theologians Society for h.s. and college kids (I only wished they’d open it up for all ages!). St. Louis also has Theology on Tap, and St. Monica’s parish (yes, out in West County-but what are you gonna do, that’s where the people have gone) has a young adult coffee house. When I was growing up, I didn’t think the Church had anything “extracurricular” (i.e., outside of Mass) like Protestant denoms did, but now I know I just didn’t know where and how to look for it. Yeah, you might have to drive a bit if you live in the City, but we have a peculiar problem here w/ driving anyway-everyone drives, our public transportation system is awful, and outside of the City, everything is designed for cars, so it’s nearly impossible to walk anywhere (one of things I don’t like about being way out here, but my parish is the main thing keeping me from wanting to move).
I’ve only visited Chicago a couple of times (and I know St. Louis has serious Chicago Envy

), and I don’t know much about Cardinal George (he’s Archbp of Chicago, now, right?), but w/ being blessed w/ Raymond Burke and being in a “red state” (even though the City itself is blue, the outer suberbs are still red), I’d have to say, even if the numbers are smaller, St. Louis is probably more orthodox. JMO
In Christ,
Ellen