Help!
A friend is going to Chicago for the first time, solo & wants advice on where to go and what to do for fun in a week. Single guy wants to have fun. Tips??

So many options, so little time! What does your "friend" have in mind? Meeting girls? Meeting guys? Dining out? Jazz? Museums? Sports?

Wherever I go I spend at least a day or 2 on my own. I walk for miles through the metropolitan areas and get lost. I wander in and out of shops, museums, and always take the city's public transportation. Tell your friend to make sure he really explores; i.e. go to different neighborhoods...Wicker Park for example is lively, used to be more eclectic than is now, but worth visiting. There's even a bed and breakfast there on a quiet pretty little street...and convenient to public transit.

I second Ken's suggestion - let us know what your friend's interests are and we'll give you loads of information. Chicago is a great city!

Go see a comedy show at Second City -- they are hilarious!

Depending on interests...
the Architecture Foundation boat tour (trust me - fascinating and worth the time and $$ but reserve a day in advance - is usualy sold out). Art Institute of Chicago... a quick trip to the Bicycly Musuem on Navy Pier... evening at a blues club - for more authentic experience choose one such as Checkerboard Lounge but to hang with and meet other single folks best bet is one of the midtown blues clubs such as Buddy Guy's Legends or Kingston Mines... lunch in the Hancock Tower - fantastic view and decent food... wandert eh neighborhoods and check out the coffeehouses and cafes - Lincoln park, Gold Coast etc. I went solo and although I was there for business had a few days to do the above - well worth the time although meeting other folks was not on my agenda so your mileage may vary.