It's tough to know exactly what you mean by 'area'. Are you looking for somewhere you can walk to from Second City? Either way there are plenty of Italian options within 30 second walk of Second City, the top two being Topo Gigio (closes at 9:30) & Trattoria Roma (closes at 10).
If you want sushi within walking distance of the MSCI you are SOL. The best sushi option in Hyde Park is Sit Down, it's about 2km from MSCI, but thankfully you'll find a line of taxis waiting for you outside. If you are going to get a cab, I'd rather just get one downtown but that's your call, Sit Down is perfectly fine.
Can't advise whether to bar or tailgate other than to say if you choose a good bar you will have enjoy a great atmosphere, especially as Chicago is full of people who grew up in Michigan.
For Tuesday, Chicago is the home of the blues. You have The Blues Bar & Kingston Mines opposite from each other. Blues is a dive bar, Kingston is much bigger but still pretty divey, they are both great and I'd recommend going, there won't be many other people dressed up and if you're looking for some sort of intimate place where you can stare in to each others eyes and whisper sweet nothings to each other you should go elsewhere. There is plenty of great theatre in Chicago, I use
this link and it rarely goes wrong.