I
think I have a wedding to go to that weekend that I'm leaving that Friday afternoon for... But I'll check with my better half, since she's generally more on top of these social obligations that I am.
I think the last time we had a POAer en route to Chicago, the restaurant list basically consisted of Everest, Alinea, and some others. I've always been surprised at the number of new places worth trying that I find on
Yelp. Have a look and we might be able to make some other suggestions.
The Art Institute is, of course, a must, and the Museum of Contemporary Art is a worthwhile destination as well -- and not that far. Since you're going to be down towards the Art Institute, a walk through Millennium Park may be worth an hour or so of your time if the weather is cooperating... the Bean (I know, I know, it's really Cloud Gate), Crown Fountain, and the bridge by Frank Gehry are worth a look. Be warned, though: it's a bit of a tourist trap -- even in November -- so Friday morning or afternoon would likely be best to avoid the crowds. If you're into architecture, perhaps consider one of the
Chicago Architecture Foundation's tours. Nightlife-wise, I'd consider heading up to the Green Mill (it's a pricey cab ride from/to the Michigan Ave area, but worth it IMHO) for some live jazz in a classic spot, or maybe the Lobby at the Peninsula Hotel... a "chocolate bar", some drinks, dancing... sounds pretty good to me!
That's what I've got off the top of my head, and obviously there's tons more that I can't think of right now, but I'd be happy to come up with some more.
Anyway, if I'm in town I'd be up for lunch or drinks or something. Let me know!
Edit: And I forgot... You'll be around on the first Friday of November, so you could do the
First Friday event at the MCA... It's pretty popular monthly event that features a blooming Chicago artist, and at only $15 bucks you really can't go wrong (though the scene-sters can be a tad annoying).