1) Cubs game. Get to Wrigleyville a bit early and pregame it at the Cubbie Bear, Sluggers, Murphey's etc etc. There are tons of places on Clark to choose from. Plan to stick around Wrigleyville after the game and pick up some hotties or gay men. The choice is yours.
2)
The top of the cock for some drinks is always a fun way to see the city.
3)
Portillos
4) Architechture river tour or skyline cruise.