psweet

I think the OP's referring to that pink on the forehead and face.

Winter Chipping Sparrows can be a mess -- they show a fair bit of variation in how much contrast there is in the face. I've been thrown by a few myself.

Apparently Red-bellied show a good deal of geographic variation in the forehead color, with birds up here (northern Illinois) being nice bright red there. In South Florida, they show brown foreheads with little to no red at all. In between, you can find intermediates -- I have shots from eastern Kansas that look a lot like your bird. (The yellow/orange/red spectrum can also be influenced by diet, since all of those colors demand the right sort of carotenoids that the bird can't produce from scratch.)

Lark Sparrows have much stronger face patterns than this -- thicker eye-crescent that nearly cuts the post-ocular line, sharper contrast between the auriculars and the rest of the face, noticeably heavier malar stripe. They also typically have a strong breast spot, although that probably shouldn't be considered anything other than a supporting point. Juveniles do show less contrast in the face, but they should also have a good deal of breast streaking. (And they should largely have molted out that plumage by now.)

Welcome to Whatbird! Incidentally, Least Sandpipers are common migrants through the Chicago area -- if you go to Montrose beach a few times in September you should be able to find some.

SE Arizona has all of California's hummers plus a bunch of their own.

I can understand your problems -- this isn't a Blackpoll or a Bay-breasted. The distinct dark cheek patch, set off by a broad yellowish supercilium that connects with a yellow patch behind the cheek, argues for a young female Blackburnian.

Red-winged Blackbird.

Looks good.

This time of year, they're molting into winter plumage, which can be perfectly intermediate between the two. Although hybrids do happen, they can't happen nearly as often as they're claimed, or the two species wouldn't remain separate. Given the bill color, I don't see why it isn't a Clark's.

Looks like a Chipping.

#6 is indeed a Broad-billed -- females are often mistaken for White-eared, since they have that white post-ocular stripe. On White-eared, that stripe is noticeably thicker.

I think the bill length, as HamRHead pointed out, is deceiving on this bird. The wings don't fit any of our orioles -- even as youngsters they should show black feathers with distinct wing bars.

Yes, a Ladder-backed.

Then yes, looks like a Coop.