Hasan

Even ignoring habitat and location, the last bird looks nothing like an Evening Grosbeak. The pattern is completely wrong- EVGR are mostly Buffy yellowish with large patches of white on the wings, not black and yellow

American Redstart

Blue Jays make an extremely wide array of sounds, which can include mimicking sounds in their environment. In particular, they often make quite convincing replications of the calls of raptors like Red-shouldered and Red-tailer Hawks. This bell sound, though, is unique to Blue Jays and a pretty common sound

Definitely Blue Jay

Orange crowned Warbler

@stitch58 oops, I completely failed to read your original post, I thought both photos were of the same bird, labeled Northern. I was IDing from the first photo, which, as you correctly labelled, is a Louisiana Waterthrush. I agree with your IDs. My bad

100% spizella, and probably Chipping, but hard to say with certainty

What bird are we referring to here? Pretty sure this is two Westerns and a Heerman's

Hm, I have never been to that site before, and on eBird it doesn't look like a known location for Bank Swallow. I think it looks good for Bank, however.

Any more photos? We cannot ID it from this one.

Where in Chicago? Looks decent for Bank Swallow, but a little tricky to tell

I considered that and I suppose it could be possible, but this would be a very weird song for Redstart and I can't find a recording of/have never heard this song

The primary projection looks very long this I would think Eastern Wood Pewee, but the photo leaves a lot to be desired

Eastern Wood Pewee

Sorry, I don't think this is a Chestnut-sided. The song is quite aberrant, but for me the ending sticks out as wrong for being Chestnut-sided- rather than the single downward, emphatic note of Chestnut-sided, there's a group of three very fast notes followed by a more faint downward note, see below. This sounded very wrong to me for Chestnut-sided- an almost Redstart-like ending- and after going through quite a few pages of Chestnut-sided songs as a sanity check I concluded this is not a variation that Chestnut-sided really has. In contrast, I was able to quickly find a similar example o

Yes, one of my favorites! Been a while since I've seen one

I believe so, yes

Borealis can often be extremely light, with little or no belly band, much lighter than this bird

@stitch58 your bird is a Louisiana Waterthrush

The recording is too low quality to get an ID out of. The sound at 8 seconds seems to occur at the same time that a robin calls, and there is significant noise reduction in the video rendering it almost impossible to hear the quality of the sound.

Definitely an Eastern Wood-Pewee

That's an osprey

Black-capped does not have a song alternating between a low and high pitch like this

Carolina

Imo not identifiable, too bleached