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Milwaukee, WI is not just breweries and home of Harley-Davidson. Milwaukee does have versatile surf spots right in the city and in its immediate suburbs. Definitely worth checking out for surfing, bodyboarding, kiting, windsurfing on lake Michigan. See Milwaukee North shore u-control web cam by LakefrontCam.com.
Bradford Beach offers half-mile long beach and sand break working on NE and SE winds. See u-control web cam by LakefrontCam.com.
McKinley Beach - sandbar and beach breaks on S, SE and E winds. Parking at McKinley Park . Can be seen from Milwaukee North shore u-control web cam by LakeFrontcam.com.
Big Bay park at Whitefish Bay is known for reliable sandbar break. Waves build on SE, NE and N.
Grant Park in Cudahy . Sandbar. Works on N, NE and strong S, SE winds.
If you don't mind driving 1 hour North, check out Sheboygan, WI. If no waves at all, try their FlowRider wave machine in Blue Harbor Resort's Breaker Bay indoor waterpark.
The Windy City is reach 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.
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.