The Windy City is rich of surfspots. Word of caution - you may be ticketed for surfing here. As of 2012, only four Chicago beaches are officially open for surfing:

Kathy Osterman Beach - nice sandy beach should work on N, NE winds.

North Avenue Beach - busy sandy beach off downtown.

Montrose Beach - half-mile sand beach with breakwall. Works on NE, N, NW. Montrose Beach is the most popular windsurfing location in Chicago.

Rainbow Beach shallow sand beach with offshore breakwall. Works on NE, N and NW.

57th Street Beach - may work on E, NE, SE.

Chicago surf spots, surf schools, hints and tips - Surfing in Chicago: Top 5 Surfing Spots in Chicago for Lake Surfers!

Check out this story Chicago surfer surprised with arrest. There could be legislative change from 2012. So maybe more beaches are officially open for surfing. Still, be warned, and read the beach signs.

Lake view web cam at Crown Center, Loyola University Chicago, lake front looking South. Located between Loyola Beach / Helen Doria Beach and Kathy Osterman Beach.
See the web cam current status and playback at Webcams.travel.

Lake Michigan water temp near Chicago