Hotel wise, downtown is solid and has great stuff like the Riverwalk/Magnificent Mile/The Bean/Millennium Park/Boat Architecture Tour/etc. IMO, it is better for sight-seeing than actually crossing paths with non-working locals though so keep that in mind.
Hyde Park (ie Sophy Hotel) is another option for more black people/restaurants/vibes. In terms of Ubers tho, you will tack be tacking on ~15 minutes to your commute to most places compared to a downtown hotel tho FYI. Alternatively, you can set aside a day to hang there for things like
Promontory Point,
Museum of Science and Industry and
DuSable Museum, etc.
If you are here for Labor Day Wknd, then there will be a TON of events available. Traffic/parking will be a shyt show with lots of out-of-towners driving in too, so I'm also against getting a car. Ubers will be less of a hassle and you can always hop on the train like the locals do.
Some other events that you can slide to will be Movies in the Park by the Park District if something good is playing or googling Chicago Street Festivals Calendar to see what's going down while you're in town.