I don’t think he was scouting out shooting locations in Chicago or Boston. My theory is he was in the illegal weapons business meeting customers in swanky hotel suites. Then laundering his transactions through real estate and casinos.
Follow the money.
That would imply that he was hauling numerous weapons into lots of different hotels.
That increases the chance of him getting caught.
They might exchange the cash in a motel, but they would examine the guns in a spot where they could be fired.
Dirty dealings are done by dirty people who don’t trust each other.
Sporting events like football and baseball are mostly conservative fans regardless of what city.