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My first thought....King = CN Tower, Queen = TD or Bank of Mtl, Bishop = L Tower, Horse = Flat Iron, Rook = Casa Loma, Pawns = Queen or King or Yonge or Bloor Stores and walk up Apts.
 
Not sure if this is the appropriate subforum for this discussion, but I'll leave that up to the mods to decide.

Anyways, I would say that CityPlace is the pawns of the city, relatively unimportant (architectually at least), plentiful, and makes a small impact.
 
The bishops should be St. James Cathedral and St. Michael’s Cathedral. I think that’s a rather obvious pair of choices since a cathedral is by definition the seat of a bishop.
 
The pawns should be the TTC streetcars (downtown) and buses (suburbs).
 
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King - CN Tower
Queen - TD Centre
Bishop - Commerce Court North
Knight - New City Hall
Rook - Old City Hall
Pawn - Bay and Gable houses

AoD
 
Toronto has a grid system for major arterial roads.

The edges of the chessboard can be Humber River, Steeles Avenue, Victoria Park Avenue, and Lake Ontario. Etobicoke and Scarborough had to be omitted and apologies had to be made.
 

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