honestly just grab the Nikon AF-S DX NIKKOR 35mm f/1.8G and dont look back. i have been using this setup for months and im super satisfied with the results, especially for the price. you can usually find them for way under your 300 dollar limit, maybe even half that if you look at used gear sites. it is tiny enough that people dont really notice you taking photos, which helps a lot with that awkward feeling you mentioned. quick tip for chicago... since you cant zoom with this lens, you gotta use your feet. if something looks too far away, just walk closer. it sounds simple but it actually makes you pay more attention to the composition. the 50mm is nice for portraits but for buildings and street scenes, its just too tight. the 35mm is way more versatile for a trip like that. no complaints here at all, it just works.

late to the party but i had to chime in on this one. > i see people talking about 35mm and 50mm but i have no clue what the difference really feels like honestly i remember when i first started with my old d3100... i grabbed a Nikon AF NIKKOR 50mm f/1.8D cuz i found it super cheap at a thrift shop. huge mistake for city stuff. i spent my whole first trip to seattle literally backing up into traffic just to fit a building in the frame lol. it was a mess and kinda dangerous tbh. you really gotta be careful with the older d series lenses though. they wont autofocus on your d3500 body since it lacks an internal motor, so make sure to only look at af-s glass. i would suggest looking for a used Nikon AF-S DX NIKKOR 35mm f/1.8G on sites like mpb or keh. you can usually find them for like 130 bucks, which leaves you plenty of money for deep dish pizza in chicago. quick question tho... are you planning on shooting the really tall skyscrapers or more like people on the sidewalk? that makes a big difference for which focal length you will actually end up liking.

I'm really happy with the technical specs on the Nikon AF-S DX NIKKOR 35mm f/1.8G for a DX body like yours. Since the D3500 has a 1.5x crop factor, a 50mm lens would actually behave like a 75mm, which is way too tight for narrow city streets or big buildings. This 35mm works well because it hits that 52.5mm effective focal length, which is basically the gold standard for street photography. No complaints here, it handles low light beautifully with that wide f/1.8 aperture. Quick tip... keep your shutter speed around 1/125 or higher when you're shooting moving people at night to avoid motion blur. This lens is super light and wont make you stand out like a tourist. Tbh it is easily the best value for money under 300.

Regarding what #3 said about honestly just grab the Nikon AF-S DX NIKKOR 35mm f/1.8G, I totally get why people love it, but honestly? If you're gonna be walking around Chicago at night, you might want something even smaller and more discreet. I know the 35mm is the classic choice for a DX sensor, but sometimes the Nikon AF-S DX NIKKOR 40mm f/2.8G Micro is a better bet for a beginner who wants sharp shots without drawing any attention. It is just as compact and the extra bit of reach really helps when you want to capture details on buildings without having to get too close. Plus, it's super reliable and feels way more solid than some of the cheaper plastic options out there. I have been using mine for years and I'm really happy with how it handles low-light contrast. Just my two cents, but you should definitely check it out before you pull the trigger on the 35mm. It is a solid, safe choice for a first trip.

My buddy told me the exact same thing last week. Guess he was right lol.