4. Try to form tribes.
One of the challenges with making new friends in Chicago is that it is far too easy for others to question your motives. When this happens, it’s common for the conversation to grind to a halt. Which is why it’s always preferable to get to know someone in a small group activity.
There’s also less pressure to contribute to the conversation, so you can relax, be yourself, and are less likely to dread an awkward silence. Three is the optimal number, because the conversation can’t split up into two or more separate exchanges.