We Torontonians are always considering how our city stacks up against other ones around the world. It's often seen as a sign of an inferiority complex, but just as often we are looking at what we might learn from other cities' experiences to create a better place to live right here.

Compared countless times on our forums, Toronto and Chicago are similar cities for several reasons. Besides being sister cities, both cities front a Great Lake, have dense urban downtown cores, and are similar in population. Despite Toronto surpassing Chicago last year as the fourth largest city in North America, (their Chicagoland remains much bigger than our GTA though) Toronto still has a lot to learn from the Windy City.

At the upcoming PUG Awards event on June 18, 2014, a PUG Talk entitled How To Build An Architectural Legacy: Lessons From Chicago will play a major role in the eveningJennifer Keesmaat, Chief Planner for the City of Toronto, will be joined by Lynn Osmond, President and CEO of the Chicago Architecture Foundation, to discuss Toronto and Chicago’s similarities, and what Toronto can learn about building an architectural legacy.

Anish Kapoor's Cloud Gate at Millennium Park in Chicago, image by Craig White

Chicago, the birthplace of going tall, is known as a "skyscraper city" due to its renowned tall building architecture of the 19th, 20th, and 21st centuries. With a great built legacy behind the thriving city, Chicago continues to carry forward a culture of appreciation for architecture and urban design. This has been shown with new skyscrapers like the Trump International Hotel & Tower, innovative urban parks like Millennium Park, and the Chicago Waterfront which has been brought to its full potential with a series of revitalization projects.

The PUG Awards Closing Ceremony will be taking place at the Art Gallery Of Ontario, Baillie Court on Wednesday, June 18, 2014 at 6pm. The ceremony, including the PUG Talk, is open and free to the public. To RSVP, visit the PUG Awards website.

What do you think Toronto can learn from Chicago? Tell us in the comments below!