Honestly, if you want one lens that does it all for Chicago without breaking the bank, look at the Sigma 17-50mm f/2.8 EX DC OS HSM. I used this thing for years on my crop sensor body and it honestly hits a sweet spot that kit lenses just cant touch. Its got a constant aperture which is huge for those darker city streets at night or when youre in a museum. Sure, you lose some reach compared to the kit glass, but the image quality is way sharper and feels more professional. You can usually snag one used for way under your 600 buck limit, leaving you extra cash for a decent filter or a spare battery for your trip. Stop overthinking it and just grab this, itll save your head from spinning before you fly out.

Honestly, skip the kit lens. I had issues with sharpness on it. Just grab the Nikon AF-S DX NIKKOR 35mm f/1.8G instead, its much better for street shots imo.

Jumping in here. Are you more into wide cityscapes or tight street candids? I used a variable zoom for ages until I realized I hated swapping gear mid-shoot, so I just stuck with one.

Building on the earlier suggestion, CharlieNap is right about the constant aperture. It really changes the game when you're walking around downtown Chicago and the light starts to drop. I have used similar glass for years and it is much more reliable for consistent results than standard kit lenses. Before you drop the cash, just think about these two things:

• How much are you planning on shooting inside buildings or museums where you need that extra light?
• Do you actually need the reach for architecture, or are you just gonna end up cropping your shots later anyway? If you really care about sharpness over convenience, a prime is always gonna win, but having a zoom that doesnt let you down in low light is a lifesaver for travel. Just make sure you know if you value that reach more than the aperture, since that is usually the biggest compromise.