Lawnchair? 
To give the OP some perspective on how long that took…Oak Park is about 10 miles from downtown…it borders the city.
Don’t touch any kitchen chairs. People get **extremely ** posessive of their curbside parking spots in the winter.
Accidentally posted instead of previewed, and then couldn’t finish in time for the edit window…
All the advice is great so far. The most important thing is to be prepared. Bad snowstorms actually don’t happen too often…I think I got stuck in only one last winter, and I commute 5 days a week…but when they do, you want to be ready. Generally speaking, those kinds of storms aren’t that dangerous from an accident perspective, because everyone is going so slowly that it’s pretty easy not to bump into anyone (and if you do, you are not likely to do a lot of damage at all of 5 miles an hour or less). The danger is more from being stuck somewhere with no gas, no ice scraper, etc.
The lawn chair thing always cracked me up about Chicago. We get more snow up here in Minnesota, and you never see that. Well, I’ve seen it a couple times, but when the car returns, it usually has Illinois plates.
I may be wrong, but am guessing that there is slightly less demand for parking up there in Minnesota than in downtown Chicago.
I’ve never done the chair thing, now that I have a garage (thank Rod) it is a moot point. But back in the day I would just leave my car where it was until the snow melted, and just start it up every day to keep it alive. Occasionally a snowstorm would collide with a street cleaning for maximum pain-in-the-assitude and then I’d have to dig out.
A garage in downtown? How posh! 
Wow…I remember scraping at the hood of random cars until I found mine…and then digging into the car to start it. What a pain!
Now, I’m a suburbanite with a garage, too!
And the chair thing really made me irritable…especially when someone would place a lawnchair in a spot that I had dug out from!! I never had the guts to run them over, though…afraid of getting keyed.
-Cem
Yes. It’s madness. I’ve lived here most my life and the whole saving your space with a chair thing pisses me off. I don’t care if I dug out my own space–as soon as I leave that space, it belongs to whoever gets there first. It’s a public street, nobody owns their spaces, but, hey, this is the stupid “tradition” here. As much as I hate it, I’m not going to rock the boat and start a feud in the neighborhood.
I’m facing my first snowy winter, too, though I’m nowhere near Chicago, but I’m reading with interest. I do need to get snow tires, here, though; I’m in the mountains in Idaho. I also have a set of chains in case of emergency. I’m told they keep the roads really clear here, especially in town and thank Og I’m in town, but the winters are pretty brutal. We’ve already gotten a tiny bit of snow, and it’s only October. This is normal here, I’m told, but most of my life has been in places where snow is an every-few-years freakout for all.
You will all hate me, but the building I’m in has parking underneath, so I don’t have to park outside overnight ever unless I’m not at home. Nyah nyah!
I don’t know Chicago at all, but if you can afford a good set of snow/ice tires (I use Blizzaks), I do recommend them. There really is a big difference in traction, even when there isn’t much snow on the ground. The rubber is softer, and so will stick better, and it’s less likely to harden and skid like regular tires will do. Tires sold as “4-seasons” are really more like 3-seasons; they just don’t handle as well in the snow.
I once had a regular mechanic who felt they weren’t necessary (in southern Ontario), but one year he got a great price on them and decided to try them out. He was amazed at the difference! I recommend them to everyone. I get mine put on sometime in November, and remove them in April; the rest of the time I have 4-seasons. I wouldn’t want to drive in the winter without good snow/ice tires!
The worst times, IMHO for the ‘thin layer of ice covered by a few inches of snow on the windshield’ is when you have to drive somewhere during a snowfall, then park your warm car outside for several hours. But there is a way to avoid (or at least minimize) the problem.
Buy yourself a sheet of reasonably heavy plastic (like a relatively thick shower curtain, or a small tarp). Cut it so that it’s big enough to cover your windshield from top to bottom, and about 4 feet wider then the width of your car. Store in your trunk when not needed.
When snow is anticipated, place the plastic over the top of your windshield. Use the extra length on the sides to anchor the plastic by closing it inside your car doors.
After the snowfall, remove the plastic, and your windshield will be clean underneath.