Longtime lurker, don't really post a lot, but I have some feedback for you.
I have sat in the Scout Seats a few times, but the last time was in '09 (so don't know if it changed). The ticket price includes all your drinks and food. You just may want to tip the servers at different times or tip them at the end (they'll wait by the exit at the end of the game).
The area opens when the park opens. There is a restaurant that you enter off of Gate 3 where they have an all-you-can-eat buffet with a fully stocked bar. They usually have a carving station, some pasta, ball park fare (dogs, burgers, etc.) and some random other stuff. I recommend getting there at least an hour before the game. The wait staff will get you your drinks so you don't even have to get up and go to the bar.
When you are done "feasting", you can head to your seats. There will be people to usher you to area. You walk right by the visitor's clubhouse door (Sheffield was standing outside it once before during a Tigers game), but they won't let you mingle with the Sox, the opponent, or the umpires (their room is close to the Scout area as well). Just before you emerge into the seating area, there is an area to fill up on peanuts, popcorn, soft drinks (not sure why? guess for the kiddies), and ice cream treats like ice cream sandwiches.
At your seat is a different menu from the restaurant that you can order off of. The only difference between the seats and restaurant is that you can get any hard liquor drinks or wine in the restaurant, whereas there is only beer and a couple of mixed drinks (along the lines of a margarita). So you can sit there and pig out some more. The only things you don't order off the menu are hot dogs and brats. There is one server who will come around every so often and hand them out.
Lastly, about the 7th inning back in the restaurant the open a dessert bar. You can bring the dessert back to your seats. Let me add one thing, you can't bring the hard drinks from the restaurant bar back into the seating area if I remember correctly.
All in all, it is a fantastic time. The one thing that stinks is that it is a long walk to the bathrooms. You have to go all the way back to the area by the restaurant, plus they have no TVs on this walk to watch the game while heading there. It is a very minor issue, but I thought I would tell you. Otherwise you will have an absolute blast.
By the way, there is no special parking lot. If you get the parking pass, it is for the lot adjacent to Gate 3.
As a plus, Kenny came and ate dinner in the restaurant back in '06. I talked to him for a couple of minutes, basically congratulating for the year before. Good guy...
Otherwise, sorry about the length, but I think this gives you what you need to know.
As far as Chicago goes, I could go on for hours about what to do. If you are looking for a specific recommendation let me know. It is hard to make a wrong choice though...