Sorry - this turned out way longer than I expected!
I've lived in Des Plaines (about 6 years ago or so), Lincoln Square, Logan Square, and now Jefferson Park. If your DH ends up working in Des Plaines (yes, that's a suburb), and the office is in walking distance of the metra station I would look at what communities are on that Metra train line and possibly start from there. The train ride between the heart of the city and DP is very quick and much better than driving if that's an option. http://metrarail.com/content/metra/e...ystem_map.html
I do not think of Wicker Park as family friendly, though that assessment could be off. I think of WP as the Milwaukee/Damen/something intersection, and I absolutely despise driving through there. It's a madhouse with so many name brand/high end stores. To DP and I it looks like an up-and-coming Lincoln Park. But my opinion of WP is decidedly biased and I never lived there. It does have el/bus/highway access.
I LOVED living in Lincoln Square. There are several local coffee shops as well as Starbucks. Lots of independent stores and restaurants, a great park (Welles on Montrose between Western and Lincoln), a great (for Chicago) library, 2 brown line stops (Western and Damen), several bus lines, the Metra line that runs straight north/south isn't too far and could be walking distance depending on how you define it and where you are. Grocery shopping is better done by car, but there is a local grocery where you can get produce very inexpensive (we still go there). It is true that it is not the most diverse, but it is more diverse than Lincoln Park. That said, when I lived there I had a great 1 bed around $900 a month, the only utility I paid was electric. That was over 3 years ago.
Logan Square is up and coming. We left there because 1. We couldn't afford a house and 2. We weren't in walking distance of a park. To be 100% honest, we didn't feel comfortable letting my DSD (who lives in the far burbs) run around the neighborhood by herself either. However, the boulevard (Logan) is beautiful, there are some nice shops and restaurants, Starbucks (not sure about local coffee house), the el and buses and highway access. I can't remember how accessible grocery shopping was. Our 2.5 bed apt with garage space was $1,275 2 years ago. We paid electric and gas heat.
Jefferson Park - don't move here if you want urban living. My biggest mistake. It's a great family area, the schools are decent for Chicago, and I have my pick of pub trans and highway access. That's it
Really, it's ok, but not what you are looking for.
Roscoe Village I LOVE but again, not very diverse, and expensive. Rogers Park/Edgewater you have to be really careful what block you are on. My coworker (and his wife and small daughter) have a condo in Rogers Park. He occasionally entertains us with stories. Not the kind of stories most people want when they are raising kids. However, he stresses that if you are on a good block and get to know your neighborhood, people really look out for eachother.
Because it's been mentioned - Park Ridge. I wish I'd moved here, even though it's not in the city. It has more of a city feel then JP. We go to the Trader Joe's here. Recently on a Sunday we had dinner before shopping. Watching out the window we were stunned by how walkable/family friendly it was. There were couples, singles, groups of kids, all different age ranges. PR
has the metra, maybe bus?, and highway access. Metra gets you downtown easily, but you still need to figure how to get where you are going once you get downtown. I would expect PR
to also have a decent park district/library/etc but I don't actually know.
If you have a car in the city expect to pay for the city sticker, and a zoned sticker if you have zones where you live (I never have). If you choose not to because you have a garage, you are taking a chance every time you park on the street for a store, restaurant, etc. Also expect you'll probably get some type of ticket at some point
And yeah, traffic sucks.