Attending a village board meeting can sometimes be a great way to learn the flavor of a community you might be considering for your next move. You can attend those meetings virtually at your convenience in a growing number of suburbs.
The Village of Deerfield just began posting video of its meetings, joining Winnetka and other north suburban and North Shore communities.

If you are new to the area or going shopping or just planning out your day you may find the iNorthshore iPhone app a useful tool. It locates the 10 closest stores or restaurants to current location or select an area on a Chicago North Shore map to display stores, trains, tolls, restaurants at a location or browse by store type. A fun way to find your way around or plan your day. No network required & no typing necessary. http://itunes.apple.com/us/app/inorthshore/id350668130?mt=8
Daniel,
Hopefully the app is intelligent enough to know that Deerfield is not a Notth Shore suburb.
For any readers who might be unaware, there are no tolls on North Shore roads.
While we are on the topic Glenivew, Northbrook and Skokie are also not part of the North Shore.