As I Approach My First Summer in Chicago, I Am Curious About / Want Advice On...

Thanks to @TQ for this perfectly timed list request. This weekend marks 6 months since I landed in Chicago. For unrelated reasons, it's been a rough time, but things are looking up, and I'm finally in a position to get to know this city. Looking for input for sure!
  1. 1.
    What are the two neighborhoods I really need to know next?
    I'm in West Loop. I still don't know everything about it, but it's so overwhelming to try to figure out everything there is out there. Where should I actually check out next?
  2. 2.
    What do I do with my 4yo nephew when he visits in six weeks with my mom?
    We already have Cubs tickets. He likes sports and games and makes new friends easily if there are play spaces like that. He's excited to be the first niece or nephew to see my new city, so I'll have stuff to do at my apartment, too.
  3. 3.
    What is the one suburb I should get to know first?
  4. 4.
    Am I going to want a car eventually?
    Yes, I have a license and know how to drive, but I haven't owned a car in DC. Most people in DC do, and you can get more out of life there with it, but I love not having to worry about one, plus I hate commitment.
  5. 5.
    What's the best way to keep up with what's going on?
  6. 6.
    Do guys shave when it warms up? So much facial hair.
  7. 7.
    Will I ever get over my East Coast sidewalk rage?
    "Jesus Christ!" I find myself saying way too often to dumbasses who just stop right fucking there in the middle of nowhere.
  8. 8.
    Who are the most annoying visiting team fans vs. the Cubs?
    Phillies fans are the absolute worst at Nats Stadium. Sorry, Philly friends.
  9. 9.
    (I reserve the right to add more.)