re: Chicago Itinerary (Thoughts/Changes/Recommendations?)

Jumping in to second a few other suggestions already made.

Dovetail is a great beer destination. And Beyle is across the street. It's also a short walk from there to some great places to eat, specifically L&M Parkside which just opened from their retail fine foods shop. From Dovetail you can also hop on the Brown line and head south two stops and get off at Paulina. Right there is Bitter Pops (taproom + bottle shop) and The Green Lady, a gem of a beer bar.

Also second Tango Sur. Their sister location, Bodega Sur, is next door and serves alcohol, in case you weren't in the mood to bring your own. If you have to wait (no reservations at either place), go next door and grab a drink at the Music Box Theatre's lounge.

Regarding the LSU game - the "official" alumni bar is DS Tequila in Lakeview. However, the Standard is still an LSU bar (check out their Instagram). The Standard used to be the official alumni location but it switched a couple of years back. However, the manager at the Standard is a huge LSU fan. I haven't been since the 2019 title game, but it typically draws a big crowd. I personally enjoy it more than DS Tequila as Standard is an actual sports bar. DS Tequila is more of a restaurant that happens to have TVs and is more of a party atmosphere, if that makes sense. In either one, I'm sure you'd have a good time though.