Chicagoans: Something new to do?

[RoxMonster]

We're going to Chicago for a long weekend in mid-January to see Hamilton. Growing up very close to Chicago and going so many times, we've done a lot of the touristy things. I would love some help filling in the gaps of our 2.5 days there with some things we haven't done before. It'll be mid-January so outdoor stuff is out, unfortunately.

(1)The Saturday we arrive, we have from whenever we get there (hopefully around noon) until maybe 330ish open (at 4, we are doing a brewery tour of Goose Island--a Christmas gift for DH).
-I haven't been to the art museum before but didn't know if less than 3 hours (maybe even less than that) was enough time?
Otherwise, anything that might fit in this time span? We have done the main museums before (S&I, Field, the planetarium and the aquarium).

(2)Sat. night we are planning on Topolobompo for dinner but then want something to do after for nightlife. We have done Second City, we have been to Signature Lounge many times. I wouldn't mind a place to get drunk lol or go dancing or something along those lines.

(3)Sunday we have open until Hamilton, which is at 2 (probably get there around 130). Best brunch place in the city? Any other ideas for what to do? Our interests are usually outdoorsy stuff, which won't fly here in January; otherwise, any sort of maybe unique tour we could do?

(4)And finally, maybe a more low-key place for a nightcap Sunday night? (We have reservations at Girl and the Goat at 7).

Monday we will probably just grab breakfast and head home.