Gyro Plate in Greektown (the greasy joints on the corner, not the real restaurants)
Maxwell Polish (don't go alone)
Mario's Italian Ice (Little Italy hangout)
Giordano's Stuffed Pizza (deep dish pizza with another crust and sauce on top)
Damenzo's Pizza (get the "pizza puff" monstrous calzone, real cheap) (don't go alone)
Pompei Pizza (totally not typical chicago pizza, they make sammichez rolled in pizza dough)
Intelligentsia coffee - awesome stuff!
Map Room - Chicago Beer Society has their monthly meetings there, so how bad can it be? 200 brands, 26 taps, cask beer.
Go to Navy Pier for free music, expensive so-so beer, and Fireworks!
OK, outta ideas. Have fun!