1. Don’t say “The Windy City.” It’s an advertising moniker more than anything. Locals never use it. And “Chi-town” is out too.
2. Love the Cubs or love the Sox, but you can only choose one so choose carefully. There’s no going back and your loyalty to a Chicago baseball team, or lack thereof, is going to be taken seriously.
(And if you choose the Cubs, you have to love them even when they lose, which is a lot.)