Hmm, populations are pretty close at both just over 2.6 million, and both sitting around 240 sq miles. I guess if you count the suburbs surrounding Chicago then yes, its bigger.
Edit: The reason I posted that was because I had recalled that Toronto was the 4th largest city in North America from an article I had read. It just seemed like Stro was referring to Toronto as a "smaller" city, which it definitely is not.
https://en.wikipedia.org/wiki/List_of_North_American_cities_by_population