Can you rent photography equipment in Chicago?
Sure, why not? Check out this studio https://www.fdphotostudio.com/photo-studio-equipment/. For me, they are the best. With their easy 24/7 online booking, you can simply check for availability and book your studio online – with no deposit or card information required. Simply fill out your request in the blue form to the right on the page they will contact you to confirm.
Yes you can, but how easily depends on where you live.
My advice which follows pertains to the USA.
Usually you either have to leave a deposit (either a check, cash, or a hold will be placed on your credit card) for the full list price but some mail order rental services will sell you insurance for the item, or you have opt provide proof you already have insurance.
If you do not live in the same city as the rental agency you will also have shipping fees to pay and you’ll have a one week minimum rental period to cover the transit times on the front and back end.