> ditching the kit lens is the best move you can make Like someone mentioned, upgrading is totally worth it! Just curious, are you shooting in super tight alleys or mostly wide city blocks? If you want something tiny for street work, check out the Samyang AF 35mm f/2.8 FE. It is incredibly sharp and fits in a pocket, which is amazing for staying low-key in the city. Total game changer for quick snaps!

Honestly, if you are doing street stuff in Chicago, stay away from the bulkier stuff. I used to lug a heavy setup around the Loop and it just kills your motivation to keep shooting after an hour. I would suggest looking at the Sigma 30mm f1.4 DC DN Contemporary if you really want that bokeh, but be careful with the size. If you want to save some cash and keep your camera tiny, here is what I would do:

• Samyang AF 35mm f2.8 FE - tiny, sharp enough for streets, and leaves you money for coffee.
• Sigma 16mm f1.4 DC DN Contemporary - a bit wide but super fun for urban architecture. Just make sure to check if you actually need the f1.4. Ngl, most of the time you are stopping down anyway. Save that extra hundred bucks for a decent strap or a spare Sony NP-FW50 Lithium-Ion Battery instead.

Honestly, ditching the kit lens is the best move you can make for street photography. Since you are wandering around Chicago, you need that extra light gathering. I went through this exact debate a while back and went with the Sigma 30mm f1.4 DC DN Contemporary and I have been super happy with it. Yeah, it is a bit chunkier than the native Sony option, but the performance jump is massive. The sharpness wide open at f1.4 is just leagues ahead of the kit glass, and honestly, the bokeh looks way creamier for portraits or isolating street subjects. I have used the Sony E 35mm f1.8 OSS too, and while the stabilization is nice if you do video, for strictly street stuff, I prefer the character of the Sigma. It just feels more professional. Plus, at your budget, you can definitely find the Sigma used or even new on sale if you look around. It works well in lower light situations, which is crucial if you are shooting near the El or just catching city vibes after sunset. Just grab the Sigma and dont look back. You will be satisfied with the contrast and colors right out of the camera, no complaints from me after using it for over a year.

Same setup here, love it

Re: > ditching the kit lens is the best move you can make. Totally agree with that! If you want a different take for Chicago streets, you really gotta look at the Tamron 20mm F/2.8 Di III OSD M1:2. It gives you a wider field of view compared to the 30mm or 35mm options, which is honestly fantastic for capturing those massive skyscrapers and tight urban architecture. Its super budget-friendly and gives you that extra bit of context in your shots that 35mm sometimes misses. Plus, it is way lighter than the Sigma, making it perfect for all-day shooting without the fatigue. Just keep in mind that being a wider lens, you need to get nice and close to your subjects to get that separation. I love the rendering on it, and for the price, it is an absolute steal! Grab one and enjoy the city, you wont regret it!