@Reply 2 - good point! But the Fujifilm XF 27mm f/2.8 R WR is amazing! Weather sealing keeps gear safe and reliable in Chicago rain, and the size is fantastic!

Like someone mentioned, everyone pushes the 23mm, but I actually found it pretty frustrating. I had issues with the older Fujifilm Fujinon XF 23mm f/1.4 R being way too clunky for street work... not as good as expected and it blocked my viewfinder constantly. If I were you, I would skip both and get the Fujifilm Fujinon XF 27mm f/2.8 R WR for these reasons:

• Its a pancake lens, so your X-Pro3 will actually fit in a jacket pocket.
• It hits your budget perfectly while still being sharp as hell.
• The focal length is basically what the human eye sees, so framing is intuitive. Unfortunately, people get obsessed with f/1.4 for low light, but you really dont need it for city streets at night. Just crank your ISO a bit. This lens is much more practical for Chicago.

I am gonna have to respectfully disagree with the idea that you have to stick to the main brand glass. When I first started, I was totally broke after buying my body and I felt stuck. I ended up trying a lens from a third-party brand that most people look down on, and it actually changed how I shoot. The autofocus wasnt as snappy as the native stuff, but for street photography, it had this grit and character that the perfect lenses lack. I learned that having a lens with some flaws can actually make your photos look more unique. It saved me a couple hundred bucks too, which I used for a weekend trip instead. I think beginners worry too much about the brand name on the front of the lens. Sometimes the alternative options are more than enough to get the job done without draining your bank account before you even get to Chicago.

Congrats on the X-Pro3, its a beast for street work. In my experience over the years, picking a first prime is mostly about finding your preferred field of view. For Chicago, I think the 23mm is probably your best bet.

• 23mm gives you a 35mm full-frame equivalent. This is basically the gold standard for street because you get the subject and the environment.
• 35mm acts like a 50mm on that sensor. IIRC, some beginners find it easier because you dont have to get as close to strangers, but it can feel cramped in tight alleys.
• Smaller f/2 lenses are tiny and wont block your optical viewfinder as much as the larger f/1.4 versions. Im not 100% sure which one will feel natural to you, but I think the wider one is more versatile for a big city trip. Let me know if you need help with more of the technical specs!

Late to the party but honestly, choosing the right glass is super personal. Before you drop your cash, Ive gotta ask a couple things:

• Do you prefer being right in the middle of the action or keeping some distance?
• Are you shooting mostly during the day or hitting the Chicago streets at night too? Knowing this makes it way easier to narrow down those numbers youre worried about tho.