Scottsdale

Scottsdale is an interesting neighborhood in Chicago. On the one hand, it looks at times like the suburbs. There are a number of homes on cul-de-sacs, a number of good sidewalks that provide one of the better modes of transportation, since there are few cabs, and plenty of parking. Oddly, for all the parking, there's a lot of traffic, at least on some of the streets that border other neighborhoods.

Food

I didn't find much outside of a few chain type restaurants(like Applebee's) although I do enjoy Mattson's Steak House once in a while. It isn't one of the higher end steak joints in Chicago, but you can get a pretty decent meal there.

Retail

Shopping in the neighborhood is okay. There is the Scottsdale Shopping Center, although if I was in the area with a car, I'd go just north to the Ford City Mall, which is a lot bigger. If you lived in the area, you wouldn't be starved for a day of shopping.

Nightlife

No nightlife to speak of. I don't personally go out drinking at Applebee's. There are a few local bars, but you can find better elsewhere.
Rainey Park is halfway decent also, but again, there are better places to go for a walk or run in Chicago. I mention it if you're thinking of moving to the area. At least there would be something nearby for you to use.