As far as parking, if you’re going to be heading out in the neighborhoods anyway, I’d find a side-street that’s not permit-only and doesn’t have meters and just leave your car there for the weekend. Then take the el or a cab to your hotel. There’s no reason to spend $40 a day on parking.
To give you a specific reference point, I’m in Logan Square (on the Blue line) and there is plenty of street parking here. I’m sure there is in Bucktown/Wicker Park as well…I don’t know how close you have to get to the loop before there’s no more free parking, but I’m only a 15 or 20 minute ride downtown.
If you were planning on spending more time straight north, along the red line I’d think you could find something close to the Belmont stop or further north.
As far as food, good recommendations all around so far. In Wicker Park, in addition to Cafe Matou, which is excellent, Le Bouchon is also an outstanding bistro. I’m a huge fan of Kuma’s for burgers and beer.