If you have a car and need it to get to work or school, your living options become a lot more limited. An uncovered parking spot will cost you at least $100 a month, and anything covered or in a garage is a whole lot more.
In Chicago, the rule of thumb is the closer you are to the lake, the harder it is to park. Permit areas are generally better, but with guest passes and people parking illegally, there's still no guarantee you'll actually get the spot you're paying for.
If you're in the market for a new place where parking isn't a pain, pay attention to the kinds of buildings on that block. If it's full of large apartment complexes with dozens of units each, that means there are a lot more people -- and hence a lot more cars -- on that block than one filled with three-flats and single-family homes. Alleys full of garages and private spots are also a good sign.
Based on my experience, these are the three best neighborhoods for easy, free street parking:
1. Bucktown/Wicker Park: Usually, the hottest neighborhoods are also the hardest places to find parking. But thanks to an abundance of public transportation and hardly any large apartment complexes, finding a spot within a block of where you want to be is a snap. The only exception is on weekend nights, when residents have out-of-town visitors taking up spots. But even then, you are likely to find a spot no further than a two-block radius.
Parking score: 9/10
2. Roscoe Village: This neighborhood has a lot of homeowners, and therefore a lot of condos with garages or parking in the back. It's also not a huge destination for nightlife (no theaters and few restaurants that people travel for), so finding a spot on Friday after work isn't an issue, either. The only potential pitfalls are during Cubs games, block parties and the annual Retro on Roscoe. Otherwise, a spot within a block of your place is almost guaranteed.
Parking score: 8/10
3. Ravenswood: This family-friendly hood is also parking friendly. Mostly residential, it's easy to find a spot on almost any side street. When I lived here, I did have to circle a few times when getting home later at night, but it was nothing like the horror stories I've heard from friends in Lincoln Park and Lakeview.
Parking score: 7/10
What Chicago neighborhoods do you think have the best -- and the worst -- street parking?