I'm looking for best possible launch site options (Chicago area) for tomorrow's forecast.
Anyone?

Montrose beach will have the most wind and a nice 4 foot swell.

www.windsurf.co.uk/jem-hall-wave-suping-in-light-winds/
Stay close to the beach break. Going through it is rewarding enough and if you get a wave ride on your way in, you done great. Don't bother trying to plane or chasing the horizon-wind won't be enough and you'll miss the fun.
www.windsurf.co.uk/jem-hall-surfvive-float-and-ride/

WindSUPing and/or SUPsurfing should be good at Greenwood today. If you don't have a SUP, a floaty board and small sail (5-6 m.) should do for lightwind wave sailing. If the conditions are right, it can be tons of fun.

Thanks for the advice guys! I'll see how things develop in the next couple of hours. I'm leaning Greenwood or Hammond, better drives than heading in and out of the city. Chris, I checked out a previous post of yours last night on dropping kit and parking on the street. Any other concerns or suggestions?

Gary, I'm 95% sure that you won't have an issue parking in the gravel lot/rigging area, since the season officially ended on Sep 4. If you have any doubts, though, there should be plenty of parking on the street just to the north of the rigging area, next to the bathrooms. I'll be there this morning.

Looks like morning is best. I'll head to Greenwood padle included.

Correction... Alan informed me that there's still a possibility of ticketing in the rigging/loading area if you don't have a season pass, so probably best to park the car on Greenwood St., which is just north of the rigging area.