Just catching up on this thread. Honestly, if you're hitting the streets in Chicago, you really need to be careful with gear that draws too much attention to yourself. My advice? Stick with something compact and unassuming. I would suggest looking at the Fujifilm XF 27mm f/2.8 R WR pancake lens. It is incredibly small, almost disappears on the camera body, and keeps you from looking like a target for potential trouble when you're walking around downtown. Be careful with the wider options because they force you to get uncomfortably close to strangers, which can sometimes lead to awkward confrontations you definitely want to avoid. The 27mm sits in that sweet spot where you have just enough reach to stay at a safe distance while still capturing the vibe of the city. Just make sure to keep your camera strap secure and stay aware of your surroundings, because even a small rig can attract the wrong kind of attention if you're not paying attention to where you are. Don't worry about missing the perfect shot by being a few millimeters off; focus on being mobile and keeping your gear tucked away when you aren't shooting. It's a reliable choice that wont break your budget either. Just take it slow and get used to the focal length before your trip.

> so i was thinking maybe a smaller prime is the way to go because i dont want to look like a pro with a huge lens pointed at people. Totally agree with you there. Honestly, I tried using the Fujifilm XF 16mm f/1.4 R WR for a while, but it was just too heavy and way too obvious when taking photos downtown. Unfortunately, the build quality on some of the older f/2 primes feels a bit plasticky compared to what you pay for them, and I had issues with focus hunting in low light. If you want to stay under your 500 dollar budget, definitely look at the Fujifilm XF 27mm f/2.8 R WR. It is basically a pancake lens, so your camera will feel almost like a point-and-shoot. It is not as fast as the f/2 series, but for street work, the size is unbeatable.

TL;DR: Grab the Fujifilm XF 23mm f/2 R WR for a versatile 35mm full-frame equivalent that handles tight city spaces perfectly. Finding the right focal length is critical for street work. If you choose the Fujifilm XF 35mm f/2 R WR, you might find the field of view too narrow for downtown Chicago architecture and crowded sidewalks. That lens acts like a 50mm, which is better for portraits than candid street scenes where you need context. The 23mm gives you a wider perspective, capturing the environment alongside your subject without needing to step back constantly. Be careful with wide apertures in bright daylight. The f/2 max aperture is great but make sure you have a fast shutter speed or a good neutral density filter if you shoot wide open. I would suggest the 23mm because its weather resistance is a lifesaver if you get caught in sudden Chicago rain. The size is also compact, so you wont draw too much attention to yourself. Just be mindful that you will need to get closer to people to fill the frame, which takes practice. Start with this one, master the depth of field at f/4 or f/5.6 for better focus depth in busy areas, and dont worry about the gear too much until youve put a few hundred shots on the shutter.

Honestly, choosing between those two focal lengths is a total headache when you are starting out. I remember when I first picked up a prime for my city walks, I was obsessing over the crop factor and the math behind the FOV. Like someone mentioned, the 23mm is basically a classic, but be careful with the 35mm because the framing is just so much tighter than what your eyes naturally see. I would suggest you check if your current zoom lens has a setting to show you the focal length on screen. If you zoom to 23mm and then 35mm and walk around a bit, you might notice one feels way more natural than the other for how you compose shots. IIRC, the 35mm is often sharper in the corners, but that might not matter as much if you are just capturing movement downtown. Not sure but sometimes the 23mm can distort faces if you get too close, which is a bit risky if you are trying to be subtle. Make sure to test your favorite shots from past trips to see if you like wider environmental photos or tighter portraits. Just watch out for lens breathing if you plan on doing any quick focus pulls. It is super easy to get caught up in the technical specs, but honestly, just pick the one that lets you move faster without thinking too much about the gear.