If you have a vehicle and you have some time get ready to do a little driving. I suggest trying to ride on the South end of the lake or up along the Southwest coast of Michigan in the coming weeks, where you might find the best beaches, best winds, waves f you like that. Your drive from Chicago could be 1 to 3 hrs to get to the good spots.
Get in phase with the weather forecasts and then control your own destiny. I believe there is a list of spots with directions on this forum somewhere - have a look.
Don't give too much credence to the TV forecasts as they are too general and not focused on what we do so much.
The forecasts can change over a matter of hours and often they are not that accurate, but with a little work, a little local knowledge from others, allowing enough time to get to the launch spot you will do OK. Obviously wind direction and beach orientation/access is critical. The wind can be stronger in one place and weaker in another place even with only 20 miles between.
As skysurfer mentioned we are coming close to the end of the season for most people. The water temperatures can drop very quickly in the next few weeks and the air will certainly get much colder. Make sure you have the proper wetsuit. We have been enjoying "Indian SUmmer" for the last 3 weeks, but that is likely to change in the next few days.
Here are a few links to weather info that you can start studying: (you can modify the locations where applicable)https://www.ikitesurf.com/windandwhere. ... iteID=1955http://forecast.weather.gov/MapClick.ph ... &dd=0&bw=0http://forecast.weather.gov/MapClick.ph ... &dd=0&bw=0https://www.ikitesurf.com/windandwhere. ... n=Gmap+Obshttp://radar.weather.gov/Conus/centgrtlakes_loop.phphttp://www.crh.noaa.gov/greatlakes/?c=map&l=lm&p=a&m=wh