If you go to ChicagoKitesurfing.com and look on the home page you can see where to ride links. The Chicago area has only Montrose to ride in for that North wind and you must be certified with IKO or PASA to ride there (yes, cops and guards do check). If you want to ride in Michigan city tomorrow that's a spot that will be hopping with people. It's a little bit of a ride with a 1.5-2 hour drive, but it'll be well worth it with a sunset session and good food/beer in the area.
Adrien - 773-208-3443
7,12 Epic Screamers
2014 7,9,10,12,17 Blade Triggers
2014 132x41 Axis Vanguard