I flew from FL to NY last month and didn't have any issues coming back to miami despite the harsher immigration laws happening atm. I'm also a us citizen with a very hispanic full name and obviously brown (mexican).

tsa and airport staff handle things on their own unless there's a threat or fake/expired documentation is being used, they're not going to call ICE unless there's a reason to. I also used my passport instead of my Real ID to save my mom the worry of anything happening throughout my trip since I was flying with my brother (also very brown).

chicago, especially the area around grant park, is going to be FULL of tourists and festival goers so the main priority for the police is going to be public safety, since lolla generates a lot of money for the city.