Ok! So, I'm not a city expert, but here's some suggestions: 1)The loop is great for architecture, but I personally think the more "neighborhoody" parts of Chicago have the best vibes. The loop is the central hub for the EL (elevated trains) which are a great way to get around and see the city. I would say heading north (Brown and Red lines) from the loop would lead to the best neighborhoods for exploring if you don't your way around. Of course, in the loop, you'll be walking distance from the museums (art institute, museum of contemporary art, field museum, etc). Also, michigan ave which is a touristy shopping district. For drinks, I recommend The Bergoff Millers Pub (I think these bars were the first to get liquor licenses after prohibition) But head north if you want some adventure! 2)For a first timer, the lincoln park, lakeview, and rodgers park neighborhoods would keep you plenty busy. Lots of bars, breweries, niche shops and weirdness. Lincoln park is the swankiest of those three neighborhoods fwiw. There are other great neighborhoods, but they might be more complicated to get to. You can buy EL passes from vending machines at each station. Or you could just uber. 3) Chicago is a great music city, so you could check some local venues to see who is playing during your stay if you want to catch another show. Some of the mid sized venues are the Metro, The Riviera, & Thalia hall, but there are so many more. I have a friend who is a world traveler, and whenever he has companions from outside the country visit, he takes the to the Green Mill. It's this old Jazz bar. Great music and a great vibe.

Btw...who are you seeing at Rosemont?