deep dish recommendations?
Lou Malnati's is hands down my favorite. They're all good, though. If you get Malnatis, make sure to get sausage. I don't like sausage on any other pizza, but their Chicago style basically slaps a circular slab of it on top of the cheese. Amazing.
As somebody said above, you definitely need to check out Millenium Park type area and the lakefront, though Chicago's kind of cold and ugly this time of year, try to imagine what it'd be like in the Spring/Summer/Fall. If you're a girl (or a guy who's a shopping enthusiast, I guess) I recommend taking a stroll along the magnificent mile on Michigan...lots of nice stores. There's all sorts of museums if you're interested in that(Shedd aquarium, Museum of Science and Industry, Field Museum, Art Institute ala Ferris Bueller...now that I think about it that movie probably has a few good ideas for you).
When you talk about the 2am thing I assume you're asking about bars and nightlife? For that I'd look to the north side...Lincoln Park or Wrigleyville (bar area surrounding Wrigley Field). For these I'd
definitely use public transportation...both neighborhoods are just a shot on the Red El Line from downtown (The Fullerton stop puts you a couple blocks from the bars on Lincoln Avenue, and I think it's the Addison stop for Wrigleyville?). However, if you're a girl, I can't condone taking the red line back downtown alone at night (you'd probably be fine, but I'd still strongly consider taking a cab back to the hotel). Find a bar you're interested in, and use the CTA planner I linked above to direct you...it's $2 a ride for most public modes of transportation.
The skyline is
gorgeous at night. My favorite view is from the Planetarium. Dress warm and good luck in your interview!