If you plan to work or go outside of this city, yes! But if you plan to work or stay in the city, no! Because parking is ridiculous, and costs.
If you have a car, then you have to deal with street cleaning, and if you don’t move your car on the days they clean the streets, then you will get fined. Of course you have to deal with your normal gas, maintenance, and updates you need for having a car like license, registration, and a sticker for actually having a car in Chicago.
I honestly recommend not getting one, because there are so many options for transportation here, and easy access to it.