The River North area has a lot of options of various flavors. Several boutique-style hotels that I think might be up your alley like the James, the Felix, the Amalfi. (I've been inside the rooms in the James but not the other two.) Hotel Indigo and I think the Monaco are also in that general area and probably a bit less costly.
I like that area a lot for convenient access to shopping, restaurants, transport, nightlife. You don't want to be in the Loop proper on the weekend, because approximately nothing is open.
I stayed at the James the last time I was in Chicago, and it was wonderful.
I shall have to look into it tonight!
Nora, where are you and Tom staying?
Hotel Lincoln near Lincoln Park. Also, Yay!
what would be good hotel options?
We love the Monaco. Bob stays there all the time for work and it's really nice and convenient to stuff.
Lee!
WHEEEEEEE
I suspect the James may be a little out of my price range, especially since they don't allow Friday check-in, but I am still playing with options.
Okay, I am getting to Chicago about 1:30 on Friday and leaving at 8:00 Monday night, staying in the Monaco in between (Nora, I figured that way we wouldn't be in each other's pockets the whole time)
YAY
That's close to where I work!