Since you are just starting out and have a strict budget, I would suggest moving carefully so you dont waste money on the wrong gear. You should definitely look at the compact f/2 primes, often called fujicrons, because they are reliable and keep the camera profile low so you wont stand out.

• The Fujifilm Fujinon XF 23mm f/2 R WR is the safest starting point for street photography because it captures a natural, wide view of the city.
• Make sure to look at the Fujifilm Fujinon XF 35mm f/2 R WR if you prefer a tighter look, but be careful as it can feel a bit cramped on narrow sidewalks. I recommend buying used to stay well under your 500 dollar limit. Just make sure the lens has the WR badge for weather resistance. Chicago weather is unpredictable and you dont want moisture ruining your setup... it is always better to be safe.

> my budget is strictly under 500 dollars since the camera was so expensive. ^ This. Also, welcome to the club! The X-Pro3 is seriously a dream. Quick question tho... are you planning to shoot mostly during the day or are you hitting the streets after dark? That basically helps a ton with light stuff and saving cash! You could honestly grab the TTArtisan 27mm f/2.8 AF which is tiny and way under budget, leaving you plenty for extra batteries and snacks!

^ This. Also, Jeffrey is spot on about the pricing lately... it is getting ridiculous. I remember when you could gear up for a few hundred bucks and call it a day. Unfortunately, the build quality on some of the cheaper stuff is just not as good as it used to be. I have had my X-Pro setup for years and I have seen the prices just skyrocket for no reason. I recently tried some of the newer glass and while the photos looked okay, the price tag just left a bad taste in my mouth because it wasnt that much better than my old beat up lenses. If you are really trying to stay under that 500 limit for Chicago, you have to look at the budget lines even if they feel a bit cheap:

• Fujifilm Fujinon XC 35mm f/2 is the best way to save money. It is basically all plastic and lacks the aperture ring, which is a bummer on an X-Pro3, but the glass inside is actually great.
• Sigma 30mm f/1.4 DC DN Contemporary for Fujifilm X mount is another one to look at. It is a bit bigger but that f/1.4 helps so much when the sun goes down behind the skyscrapers. Honestly, I was pretty disappointed when I first handled the XC line because it feels like a toy compared to the heavy body of the X-Pro, but for street stuff, nobody is gonna notice your lens is plastic. Its better to have money left over for a CTA pass and some pizza than to spend it all on a fancy metal ring... just my two cents.

I think third-party glass is basically your only option for that price point. Not sure if the linear motors are as robust as native tech, but IIRC the autofocus speed is decent enough for street stuff. Honestly, id be worried about the lack of weather sealing in Chicago. If it gets misty near the lake, you dont want moisture getting into the mount and shorting something.

Like someone mentioned, the f/2 primes are cool, but for the X-Pro3 specifically, I am totally obsessed with the pancake setup! I remember my first time shooting street stuff in Chicago near the Loop... I had this massive lens and felt like such a creep lol. Switched to a tiny prime and it changed everything. You honestly need to look at the Fujifilm Fujinon XF 27mm f/2.8 R WR. It is incredibly sharp and makes the camera thin enough to slide into a pocket!

• The f/2.8 aperture means it works great even when the sun starts going down.
• 27mm gives you a 40mm field of view, which is exactly how your eyes see the world.
• It has a physical ring to change the f-stop which is super tactile. If that hits the budget too hard, the TTArtisan 27mm f/2.8 AF is an amazing alternative for way less money. Both are tiny and perfect for staying low profile!

Lol I was literally about to post the same thing. Glad someone else brought it up.

Just catching up on this thread and man, I totally feel your pain about being lost with the gear stuff. It is honestly so frustrating how expensive this hobby has gotten lately. I have been shooting for a long time and even I get annoyed at how every recommended setup costs a small fortune. It makes me so mad that people feel like they cant just start taking photos without dropping thousands. It really shouldn't be this complicated or pricey to just walk around Chicago and take pictures. Since you want to keep it under 500 and still get that classic look, you should check out the Viltrox 23mm f/1.4 AF for Fujifilm X. It is basically a high-quality alternative to the expensive Fuji lenses but way more affordable. It is great for the city because it is fast enough for low light stuff. If you want to really learn what those f-stop numbers do, honestly, go with a manual lens like the 7Artisans 35mm f/0.95 for Fujifilm X. It is dirt cheap and having to physically turn the rings helps everything click in your brain way faster than an auto lens ever will. You got this, the X-Pro3 is an absolute beast once you get the hang of it.