Welcome to the City! It's a bit a change from Miami, but I am sure you will find it to be an exciting place to live and ride.
A wet suit is definately a requirement for riding around here. You can find a decent supply at Windward Sports http://www.windwardsports.com/
. I recommend getting one full suit with 4 or 5mm thickness on your core areas (a dry suit would be needed for any water too cold for a 4 or 5 mm), and a thin shorty with 2mm thickness
The only option for riding in the city is Montrose and a streamer is required (you can check out all the details for streamer certification on the "open forum" sitcky link - http://chicagokitesurfing.com/kiteboarding_messageboard/viewtopic.php?t=6285
). The convenience of Montrose can't be beat. However, there are a lot of better riding options outside the city that do not require any sort of certification to ride. Check out the "Where to Ride Section" for a list of spots and directions on how to get there.
BTW - this posting would be more appropriate for the "Open Forum" section.