First time there, two days on my own: weird/unique museums and best whiskey bars?

Hi all! I'm a busy mom with two young kids and I get my first solo trip in 7 years so I'm really excited! Going to Chicago for a business meeting and I'm adding two days for tourism. I would love recs for:

--bizarre, tiny, unique, or strange museums (I live in a city so I have access to all of the regular types of museums)

--The most hipster coffee shop

--Best bourbon bars

--Where's the best site to get performing arts tickets and any suggestions for shows? I love musicals and I'll be there in March '25

--any improv groups?

Thanks in advance!