It is possible to live without a car in Chicago and even in some parts of the suburbs as the public transportation system is very developed and well connected. The freedom of having a car at your disposal at any time, however, is difficult for some people to live without.
It is rather easy to drive in Chicago mainly because the map of the city is very straight-forward, laid out in a simple grid (as explained in the city structure section). Two main problems can make it expensive and frustrating, however. The first problem you will encounter if you choose to have a car is parking. Parking can be difficult and expensive. Therefore, it is very important to determine if there is a parking availability where you will stay. Ask yourself if it will be easy to park in the street after 6.00 pm when you come back from work? Is there a parking lot available inside the building? Parking your car is even more difficult in the winter because of the snow. Optimally, it is a good idea to have an indoor parking lot. If you decide to park in the street, check if you have to pay for a parking permit. A lot of blocks require one, but generally speaking, the fee is inexpensive. On the other hand, It is very expensive to park downtown. It costs approximately $25-30 a day. The minimum rate is $13 for an hour. Therefore it is not recommended to go to work with your car unless your company has a private parking with special rates or free spots.
The second problem you will inevitably experience is traffic, especially on the Expressways during rush hours (from 6:30 am to 10:30 am and 3:30 pm to 7:30 pm). Traffic can be worse due to weather conditions (especially during winter) and road works.
Moreover you have to keep in mind that you will have to buy a city sticker, which can cost anywhere from $10 – $120 depending on the date of registration and the type of vehicle.
A positive point is that gas is not expensive despite an increase of its price the last years. Americans complain about fuel costs, but gas is much less expensive than in Europe, for example.
Finally, it is not necessary to have a driver in Chicago or generally speaking in the US. But of course, it is possible to get one. Here is a list of companies for drivers or chauffeur services: