The former Bayern Munich, Manchester United and Germany star was unveiled by the Fire to a packed room of journalists, some with more of an idea about football than others.
The first question Schweinsteger was asked set the tone for the rest of the press conference and it couldn't have been more awkward for the German.
"With your addition to this team, is it a fair expectation to see a clear pathway towards a World Cup, competition, come out of Chicago?"
After receiving plenty of confused looks and Schweinsteiger asking for clarification from Chicago Fire officials, the journalist reworded his question.
"Let me re-phrase. Do you expect now that you're here, Bastian, that a World Cup goal for Chicago Fire is a realistic expectation?"
By this point Schweinsteiger, who of course won the 2014 FIFA World Cup with Germany, couldn't maintain a straight face and club officials stepped in to explain to the journalist that club teams could not compete for the World Cup.
Not long after, Schweinsteiger, who retired from international football last year, was asked yet another baffling question.
"Do you plan in the future to represent your country again in international play?
A confused Schweinsteiger was initially lost for words before explaining to the reporter that he had brought an end to his international career.
"I've retired from the national team," he said.
"I said goodbye to Mr Joachim Loew (Germany coach), so that's done."