I've been here about three years now. I live right on the border of Bucktown and Wicker Park, two neighborhoods that butt up next to each other. I've lived in or near Wicker Park all three years. My husband has been here seven years and has lived all over the north side.
One thing I love about Chicago (and many other dense cities) is that you can find a neighborhood to fit you.
Wicker Park is an ecclectic neighborhood. Mostly early twenties through early-thirties, people with either no kids or very young kids (although people tend to leave after having kids as WP isn't all that kid-friendly). It's a little gritty, with a lot of mid-range bars and restaurants and a couple upscale and trendy places too. There are two of Chicago's most popular small music venues, SubT and Double Door. It's very dog friendly - two dog parks and a lot of restaurants let you bring your dog on their outdoor patios. Some stores have "dog parking" or places to tie your leashes while you are inside. There are a lot of hipsters in this neighborhood but really, it's such a mix of different types of people, which is why I like it.
Bucktown and Wicker Park are separated by North Avenue. Bucktown is more grown up than Wicker Park. People tend to be late 20s to late 30s, with a kid or two. You can see the difference in the two neighborhoods when you cross North Ave. You go from bars, pubs, cool boutiques and second-hand resale shops and stores like Urban Outfitters and American Apparel in WP to more upscale bars and restaurants, more beer gardens, and trendy boutiques and stores like Bebe, BCBG, and Lululemon in Bucktown. Lots of yoga places for young mothers and way more strollers and children than you'll see in Wicker Park. Lots of pretty, quiet streets.
I like living right on the border, although 90% of my time is spent in Wicker Park.
If you have any questions about neighborhoods, let me know! A lot of where you'd like depends on your age, whether you have kids, whether you need to be close to public transportation (if you use it to get to work, this can be really important, esp in winter), if you like to go out and what kinds of places you enjoy (ie bars, restaurants, cultural events, the lake and parks, etc).
[This message has been edited by ChiAggie (edited 3/15/2012 1:35p).]