How would one prepare their self if moving from Nashville, TN to Chicago?

Jack - Before you find a place to live, you need to first find the right community that meets your needs and lifestyle. Chicago and its surrounding suburbs are very diverse. Even within a city itself, the north-end for example can be very different from the south-end. So you have a lot of choices. Typically you want to have a good handle "must-have" items like your budget $, commute time constraints, and importance of good schools. Then you want to think about the "nice to have" items like the types of neighborhoods, the city's amenities, older crowd vs younger crowd, parks and facilities, etc. Finding the right community can be daunting and time consuming. However, there are websites like www.homeologychicago.com that can assist your community search.

Be ready for less Country and more Jazz/Blues! Seriously, Chicago is the friendliest Big City in the US - and certainly the prettiest! We may not have many Western Shops (check out http://www.alcalas.com/ if you miss boots/hats), but we have lots of parks, lakefront trails, nightlife, and the best ethnic restaurants! Don't be worried about the transition - all my relo clients have reported how easy their transition has been, how easy it is to get around the city, how friendly/open Chicagoans are to others, and how pretty this city is. Welcome to Chicago!