That is an easy one. Just list your 10 favorite wrecks. The OP is in Chicago so they should be within a reasonable distance from Chicago. Visibility in Lake Michigan runs from 100 ft in the early spring to 40 to 50 ft in the summer. The attraction is some of the best preserved wrecks in the world.
Let's start with:
S.S. Wisconsin
Lady Elgin
St. Mary
Wels Burt
The Straits of Mackinac
Material Service
Seabird
Rosinco
MST728B
Fin Seeker
The Straits have magnificent diving for all skill levels, you can make almost all of the divers recreationally or you can go out to some of the deeper ones and stay longer for some technical diving.
Also, all the Great Lakes have some great diving and outstanding preservabliy, wrecks like the Windiate and Dunderburg are very intact even today