I'd recommend a trip to Morton Arboretum, they'll have a nice variety of all these so you can really get a good feel for the differences. I've just never seen a scarlet oak in Chicago so I wouldn't feel safe recommending it (might just be a fluke). I mentioned the city proper thing as I've been told in Chicago that east of Damen the soil is more acidic, I'm west of that line, but I really heavily amended my entire yard (rototilled in tons of mushroom compost and manure) a few years before I planted the NRO, and it turned a great orangish-red last year. I suspect that buying a NRO (or scarlet, for that matter) from an established nursery gets more reliable fall color, as they know that's what people want/expect, even though the red in the title came from the wood/lumber industry. good luck, you can't go wrong with an oak no matter what, Chicago planted burr, shumard, swamp white and shingle oaks all over my neighborhood over the past few years, can't wait until they really get established.

As of now my Pin oaks and Nr Oaks are still reddish. The Sunday night winds Nov 17 th have made my Metasequoia and many Q. Bicolors lose leaves. I want to add that the local areas Q. Alba (white oaks) are Russet red, but I have 3 in my yard and the 2 that I gave powdered seaweed to in 2009 or 2010 have had ugly fall color. The trees grow fine in the growing season, but the one that I never gave seaweed powder to is Russet red. So I guess PH is an issue. I will be removing the red colored Q. Alba one if my Live oak "late drop" does good this winter though. I would keep, if the "late drop" live oak croaks. I would dig it up and put elsewhere, if the late drop stays alive, if not for the many shade plants that are in the root-zone of the Q. Alba. So if the Live oak "late drop" does okay this winter, I have to cull the Q. Alba. I can grow them anywhere in my zone, but if the live oaks are fine after winter #2, I must keep them where they are, so they will hopefully continue to do well. Of course the Beech is still red tannish.

If it's a big enough tree, I'd seriously suggest hiring a certified arborist. Trees are a big investment and I don't try to second guess treatment if I'm not confident enough about what's causing it. We tried to grow a medium-sized Shumard Red Oak two springs ago, and in the span of one year it died from a double whammy of slime flux and borers. It was a messy and depressing death, and it was obvious by about mid summer that the tree wasn't going to turn around. One thing I've learned from arborists is that too much water looks the same as not enough -- you'll get the same burnt tip appearance on leaves. I'm not saying you're watering too much, that's just the other side of the coin. There's all sorts of other factors that can cause browning, so you'd have to get someone to look at the whole tree, see what the leaves look like from bottom to top, check the soil around the tree, see if anyone's spraying anything in your neighborhood, check the leaves against diseases, etc.

I'd avoid the shumards from the big box stores - they're almost certainly southern provenance trees (likely from nursery growers in TN). I've tried southern source shumards more than once, and had very poor results (winter dieback, chlorotic foliage). You'd be much better off with a locally grown shumard from a more northern seed source (if you can find it). Maybe one of the growers in the Lake County area would have them? Though I've never tried Nuttall oak, based on its native range I'm guessing this species wouldn't perform any better than southern shumards. The Quercus experts may chime in on this. I also think at times some nursery growers have confused these 2 species, unknowingly labeling Nuttalls as Shumards.