Greetings from one of the bastards at Game Time! (The same bastard who will be donning a Hawks jersey as part of losing a bet)

The reason I'm posting over here is pretty simple: I'm trying to plan a small two or three day vacation this summer with the ladyfriend and we're trying to do this on as small of a budget as possible. What I'd like to get from any of you is any and all advice on how to see a majority of the landmarks of Chicago, eat/drink/get thrown out of some places you all would recommend (the places locals actually go and not touristy shit like Ed Debevics), and just generally have as much fun while managing not to spend an arm and a leg in the process (Need the money to get Oshie hammered some more). Any and all tips are welcome:

• When to go? (We're thinking mid-July, mid-week would be cheaper than weekend, right?)
• Where to stay? (Saw a HoJo for 80 bucks a night about 6 blocks from Michigan Ave)
• Mode of travel. (This is contingent on there being a flight/bus/train fare cheap enough to justify it, but how useful is the El and all that for getting where I want to go? I'm fine with the idea of driving my car everywhere but if I can avoid a hassle on the cheap I'll do it)
• Where to eat and drink? (Suppose I'll even want a slice of this deep dish pizza I keep hearing about)
• Any events or shit like that during the summer? (The sporting evens are easy enough to keep track of, but anything else?)

So let me know how I should go about all of this. I haven't set an exact budget, but for this post's sake, let's say I'm looking to do 3 days at around $400-500 bucks.

Or you could just tell me to get the hell out of here and go back to my cave in St. Louis. Either way.

Thanks for any help.