1: this is lovely. A really nice shot, although I'm not sure if the colour is working to its advantage. I realise it's probably natural ambient light, but the empty sky looks too warm with the orangey hues. It's probably just the perspective, but the building looks a it skewed.
2: personally I try to avoid obvious writing in images if I can. The eye is automatically drawn to it so quickly that it tends to upset the rhythm of the piece. I like the composition, but again there seems to be a tilt on the camera!
3: this photo of the roads works really well for me. The abstract composition and the recognisable road markings creates a pleasing sense of cognitive dissonance. Being picky, I'd have preferred the light splashes on the left of the image to be higher up: they are currently at a middle height and look too balanced among the rest of the diagonals.
4: Chicago Work Out logo. This one doesn't really do much for me. The logo is okay, but there isn't really any context for why I'm looking at the image of it. What was your contribution to the image? What makes this a photo you have taken, rather than just the work of a logo designer and the person who put it there?
5: Overgrown bench/pipes/dark-thing. Nice. I like it. It works well as a thematic study of the nature/man relationship. The foreground where the plants are overcoming the dark object nicely balances with the view of the city that is obscured by the overgrown slope. I'm not sure that the composition is doing you a huge amount of favours, but it's not too bad either and there's enough going on to make the image work.
6: Life Guard. There's that tilt in the camera again! I really like this one, other than that tilt. The apparent symmetrical image degrades the more you look, presenting a nice balance between light and dark on either side. The blue glow behind the windows and the prominent door on the left seem part of a larger, but unknown, narrative. The words 'life guard' suggest that the building occupies a spot between the light and dark, life and death. Was any of this intentional?
Good stuff. This is one of those cases where text draws the eye, but you wanted the eye drawn continually back to that area anyway, so it works on your side.
7: Bus stop. I'm not sure what you were going for with this one, but it doesn't really do anything for me. The composition seems slapdash, the image doesn't seem to have much deliberation or intention behind it.
8: Blurred car lights. It's a nice effect, and I quite like the dark lower half of the image, but I feel like I've seen blurred headlights so many times now that it really needs to be something special to turn my head. This is another case where the limited palette of colours, and the warm orange tones, aren't really helping you. Can you get a more extensive range of colour picked up by your equipment?
9: Parking meter. It's okay, but not the best of the bunch; however, I do really like the white shine on the top left of the meter. The focus for that part is spot-on and the light gives a lovely sense of the texture. You could probably have zoomed in on that area, gone for a really purely compositional image with very little recognisable figuration, and produced a stronger final shot.
Out of the bunch I like the 'life guard', the road, and the skyline pictures the best. They each have flaws, but they each have some very strong elements.