As far as general tips and advice, don't rely on the CTA much. The trains have construction zones and slow zones and the buses move slowly and there aren't enough of them. Use it, but be prepared to be frustrated when you have to wait a while for a bus or train or when one comes and it is full of people. (yeah, we love to hate it)
The good news though, if you're going to be staying on the North Side/Lincoln Park, is that alot of what you'll want to see and experience are within walking distance or just a short cab ride away. The air (who wants to see the water part, really?) show starts on friday (through sunday), and one thing i really enjoy, when i have that day off, is just hanging out on the North Side/Boystown, at an outdoor table at a coffee place and seeing and hearing the planes go by overhead and make the whole neighborhood shake!
If you like Thai, Korean, Vietnamese food, Chicago has it in abundance. From neighborhood gay-friendly thai places like joy's noodle on broadway across from the gay-ish caribou in boystown, to korean place jin ju in andersonville (another gay 'hood, but a bit older, quieter and more lesbian-ish), to a bunch of places on argyle street, right off the argyle CTA station (and blocks away from andersonville).
I like the suggestion to have lunch with oprah, too. Me and her, we got a regular standing monday lunch date, though i break it sometimes to hang with nate dreamy berkus or kanye west. ;)
The architectural boat tour is a great idea too, not just for the tourist aspect, but also just taking a boat tour on the river is a great way to see downtown and august in chicago is usually pretty steamy and that's a nice way to get some cool river breezes. If it rains (or doesn't) and you're near michigan avenue, i'd also recommend getting a drink or two at the bar on the 95th floor of the hancock building. this way you don't do just the plain old, go up to the top of a tall building and look out the windows and leave, but instead you get to enjoy a 95th floor view, but also with a cocktail or two, which cannot be beat.
If you like theater, check out the Theatre on the Lake, a quasi-outdoor theatre right on the beach in lincoln park. they put on one week runs of shows that have been critically acclaimed in chicago the previous year. And i also recommend getting a copy of Time Out for listings of almost everything you'd want to see.