Anything Trump was to do would be met with riots approved by the Mayor, multiple law suits, court orders to cease and desist and calls from across the media for Trump's impeachment.
Once he does respond all the decades of problems caused by the progressive liberal democrat socialist party will become the fault of Trump as the demoncrats will have successfully completed a transfer of ownership.
Anything less than moving in and taking over the entire city of Chicago will fail so that won't happen, best to just let it be and allow it to self destruct or he will windup with same mess as he has with obamacare, make them beg for the declaration of Martial Law.