Yes, but they will search it for contraband... liquor or weapons.

Yes

I brought one in to a game without issue, just a smaller one that fit into my backpack.

5-6 miles? Too far to walk.. CTA red line is the way to go, or Uber.

Yes

If healthy, absolutely.

Yes absolutely. They check bags, mainly with a baton, but if suspicious they will look more thoroughly.

Yes . had my phone and a camera

Its time for the cubbies starters jackets.....pretty much!!😉

Yes