There were supposed to be more of them. It was in the Plan. (You know which Plan.)
But maybe it’s not so bad. Maybe we just need to do a better job of appreciating the diagonals we have. The paeans to Clark and Milwaukee and Archer are numerous. What about Talcott or Forest Preserve or Manor or McDowell or Vincennes or Exchange or Van Vissingen? For that matter, what about all the streets only masquerading as upstanding members of the Grid? On the west side, road after road gets corrupted at North Avenue, each one dancing to the east for a brief stretch: Kedzie and Pulaski and Cicero and Central—all diagonals for a moment. Lake and Devon and Grand, too, loosen up once they get far enough away from the shoreline. Even Michigan Avenue runs diagonally, if only for a block or two, just north of Old Fashioned Donuts in Roseland.