Your username makes me think you're a local, so you might not be used to taking the train to....well, anywhere. I had friends in Schaumberg/Rolling Meadows (NW/W side of the city) and I used to love to catch the train from there...I think from Arlington Station, something like that. About an hour's trip and you see Chicago from the outside/in, arriving downtown, where your choices are endless. THIS is touristy, this idea, but if you get a chance to take a boat trip down the Chicago River (and onto Lake Michigan), weather permitting, it's a good time.
It's kind of funny you mention that- I was actually born in Chicago BUT we moved to Houston when I was really little, so I'm basically a Houstonian. I plan on relying heavily on the rail while I'm in Chicago. I've been back a few times, but a lot of it was visiting family and friends and I've never gotten to really explore the city (outside of the touristy stuff) as much as I wanted to. Whenever I travel, I enjoy going to places with a local feel (and hopefully fewer tourists). Hole in the wall, etc. is all fair game to me. Regardless, thanks for the heads up, y'all are giving some great ideas. Additional info- I'm thinking about going the weekend of July 22nd. Incidentally, the Astros will be playing at Wrigley so I will definitely make the trip to see them play.
I second Lou Malnati's for the best pizza. If you're going to be near Wrigley and are into clubs, you should check out Smart Bar. Just don't go too early because it will be a ghost town. My favorite club/dive bar in all of Chicago is Neo. That is the one place I'll make sure I'll go to next time I'm in town. I read somewhere that it's the oldest nightclub in Chicago. It has a goth theme going on, and they play new wave and industrial. The people are cool, and it seems to lack the sleaze of most clubs. If you do decide to check it out, wear black.
Third. Gino's is too watery IMO. Also, go to Garret's Popcorn for a snack. The cheese and caramel mix. So addictive. I was going to suggest going to the Art Institute of Chicago on Thursday night because they have free admission from 5-8pm...but it looks like they stopped that. For some good moderately priced Italian, I recommend Volare.
My trip is coming up- thanks again for all the suggestions. Any tips on tickets for wrigley? Meaning should I just go ahead and buy them direct or do you guys think that I can get them cheaper these days if I wait til gameday (or do something else)? Its going to be Astros v. Cubs, not exactly a hot ticket haha.
We were just in Chicago for a month and we used Craigslist for Cubs tickets. We bought them way under face value and there really isn't a bad seat in Wrigley. Also Lou Malnati's is awesome along with Giordano's, you really can't go wrong with either of those places as far as deep dish is concerned.