As far as I remember the Chicago thread on this board is pretty decent for spots. Anything in particular you're looking to skate? Some of the spots may have been torn down or skate stopped in the thread, though. Feel free to ask about em. The new grant skate plaza is a decent warm up spot, might be able to find free (or at least cheaper) parking south of Roosevelt on, I believe, wabash or at by the Trader Joe's on the intersection of Wabash and Roosevelt (at least that's what I've heard, check for signs and lots). It gets pretty crowded there though. Seawall is pretty close to there, there's a cool ledge spot outside of the planetarium and another ledge on the corner of Columbus and Roosevelt. Chase tower is more in the loop has stairs, ledges, slightly banked walls for wallrides.
http://www.slapmagazine.com/component/option,com_jfusion/Itemid,4/index.php?topic=49438.0 Always a hard time thinking of food and bar spots when people are looking for recommendations. There's a couple Al's beef spots around the city for a good beef sandwich. Maxwell street hotdogs Chicago style. Ricobene's breaded steak sandwiches are good. There's a place called sweet station in China town that's pretty good for Chinese food and open late. It's pretty close to a place called Reggie's rock club which is a bar that a few of my buddies like to go to, kind of a punk rock vibe I guess, they have food too, not sure how long the kitchen is open though. Might get shat on for pizza recommendations but I like Giordano's deep dish haha. A place called The Art of Pizza is also really good.
Feel free to ask questions, get more specific with spots, etc.