Upvote:1
It would be very difficult for you to find such a spot. About a year ago, any of the free and clear parking I knew of was sold off, and meters were installed.
Even if you do find a spot, there are a lot of reasons in the city for which your car would be towed. Construction pops up with little notice. If you're more towards downtown, parades and other temporary permits will block off streets. Street festivals are a problem in summer months in neighborhoods.
I would recommend snagging a parking spot with SpotHero, Park Whiz, or one of the similar parking services. They're a lot cheaper than a typical lot, and you know where you can park ahead of time. I usually would go for the spots under the CTA tracks, as they were cheapest and there was always parking available.