Traffic and city driving you get used to very fast. There's no getting used to parking issues and the hoops you have to jump through. Since it was fully privatized the meter rates are through the roof and it's almost 24/7 365 days a year (yes parking tickets on Christmas day), higher rates than Manhattan. Just something you have to suck up because even if you have your own spot you have to head out places. I drove less every passing year I lived there and was happier for it. Final year I just used Uber and ZipCar car sharing when I needed a car.
The guy who said minimize your commute or work it into CTA trains and busses nailed it. That said parking and winter were the only things I didn't absolutely love.
To add to this:
Yeah, if you are always paying the meters, you will be wasting A LOT of $$$. Most areas in the city are $2.00/hour. But, once you get into the more business district areas it goes up to $4.00/hour and in the Loop it's up to $6.50/hour.
Some areas are now free on Sundays and between 10pm-8am, it just depends on the area so check the meter box.
And yes, they will ticket you so don't think you can make a quick stop and not pay.
Also, when parking on residential streets, make sure it's not zoned parking unless you have the correct parking zone sticker. Most residential areas in Chicago require Residential Parking Permits. I parked in the wrong zone last fall for about 15 minutes thinking I could get away with it... NOPE, walked outside to my car and a $75.00 ticket.
So, as you can see, parking is a huge hassle in Chicago. The less you have to drive and park, the more enjoyable your life will be.
And for the love of God, pay your parking tickets. My Co-worker got "The Boot" last week. It cost him $300 to get it taken off + his unpaid parking ticket fines. The total came out to around $800 all because he forgot to pay a couple of parking tickets issued about 10 years ago. Chicago loves to give people The Boot.