I have a preference of films that I use regularly. For daytime street shooting I use either Kodak Tri-X or Ilford HP5+. I find the ISO 400 speed of these to be very adaptable to a wide range of lighting situations. In general I use a yellow filter and the Sunny 16 rule with B&W films and my Leica M-A, but I do carry a Sekonic light meter for checking the light if I feel unsure about it. I generally use these films at ISO 400, set the shutter speed to 1/500 s and adjust the aperture as needed.
Ilford HP5+ (click to enlarge images)
Nighttime is a very different story. If I want B&W, I’ll use Ilford Delta 3200 and push it 2 stops in processing (no filter used). I nearly always open the aperture all the way to f/1.4 on my Summilux 50 mm lens, and shoot at 1/60 s. With city street lighting this exposure seems to work quite well most of the time.
Ilford Delta 3200 (pushed 2 stops). Click to enlarge images.
I really liked my initial experience with CineStill 800T for night shooting in color. Again, I keep things simple by shooting at 1/60 s and f/1.4 and push 2 stops in processing. The halation effects that I mentioned previously work well for me with street shots and give an interesting and dramatic effect around lights. The film can be used with an 85B warming filter in daylight (with appropriate aperture and shutter speeds) and gives a very nice color palette, at least to my eye. The daylight shots look somehow like older 1960-70s photos, but I like this look.
CineStill 800T (pushed 2 stops). Click to enlarge images.
I have a couple of upcoming visits back to Chicago this summer and will be shooting there again.
Thanks for reading!