Do not even think about driving in the Loop. It's crazy and so are the drivers. I work downtown and I take public transit. I have no problem with it. El trains and buses run pretty frequently (some 24 hours) and you can buy visitors passes, 1-5 days, ranging from $5 (1 day) to $18 (5 days)...normal fare is $1.75 and transfers are 25 cents, so the passes are a good deal.
By the way, I did a bit of googling and found that the Best Western River North, which is also right downtown, has free parking. Here's the website:
http://www.rivernorthhotel.com/
As for places to go, some say it is overrated but I happen to love Wrigleyville. Yes, it is fairly yuppified but there are some fun stores and restaurants around there. And Wrigley Field is a shrine.
And you can also stop by Tribune Tower and say hi to me.
