Chicago!

[LukeA]

I lived in Chicago for five years, and still go back 2-3 times a year for fun. For the famous touristy stuff, I concur with FMLex, who summarized it quite well (the only thing I fervently disagree on is Navy Pier. Don't waste a minute at this tourist trap) What are some interests (food, shopping, sights, etc.) that you and your friend share? Chicago has so much to explore & enjoy off the well-worn tourist paths.

I will say that a great pre/post-show spot to grab a bite and a drink right by House of Blues is the Billy Goat Tavern- http://www.billygoattavern.com/ - the rare place that's loved by locals, tourists, and convention-goers alike. Plus, if you're a fan of baseball (& familiar with the Cubs) or Saturday Night Live (the Cheeseborger Cheeseborger sketch), this place would be no stranger to you.

As for hotels... Priceline is your friend. I routinely stay at one of the Hiltons or the Hyatt downtown for about $50-$55+ tax- and as long as its not a big convention weekend (next month should be fine), you should be able to get the same rate for a 4-star hotel. Check out www.biddingfortravel.com