Here's a collection of what I think are some of the coolest maps of Chicago I've ever seen. One of the things I love about the city is just the way it was planned and has a beautiful, orderly pattern of streets that radiates out from a core, right where the seeds of the city were first planted. It's on view from the beginning, in the early maps. Later cartographers and artists took liberties in presenting the cityscape in different ways, highlighting certain elements like new transit lines, parks and boulevards, and modern aerial views.
NOTE 2: If you want a closer view of these maps, right-click on the image and select "Open image in new tab." That will allow you to get an expandable view of the image and a better look at the details.
Imaginary view of Chicago in 1779. A. T. Andreas, History of Chicago from the Earliest Period to the Present Time, vol. 1 (Chicago: A. T. Andreas, 1884), frontispiece. Source
Chicago in 1820. Chicago Lithographing Company, 1867. Chromolithograph on paper. Library of Congress. Image source
Map of Chicago in 1812. Image source.
"Map of Chicago, Incorporated as a Town August 5, 1833." Walter Conley & O.E. Stelzer, 1933. Image source.
The original 1830 subdivision by the Illinois and Michigan Canal Commissioners. Image source.
Chicago In Early Days. 1779-1857. Kurz & Allison, 1893. Source.
Lithograph by Christian Inger, based on a drawing by J.T. Palmatary. Published by Braunhold & Sonne. 1857. Source.
Chicago, Chicago Lithographing Co., 1868. Image source.
Currier & Ives.; published in Harper's Weekly (1 August 1874) Image source.
Richard’s Illustrated and Statistical Map of the Great Conflagration in Chicago. 1871. Image source.
The City of Chicago / sketched & drawn on stone by Parsons & Atwater. Currier & Ives, publisher. 1874. Image source.
Guide map of new Chicago and suburbs. Author Stine & Clark,1889. Source.
"Bird's eye view of Chicago, 1892." Roy, Peter. Image source.
"1893 Grand View of Chicago." Treutlein, Th. Eagle Lithographing Co. Reynertson & Beckerman, 1893, c1892. Image source.
"Bird's eye view of the World's Columbian Exposition, Chicago, 1893." Rand McNally and Company. Image source.
Library of Congress illustration of the official birdseye view of the World's Columbian Exposition in Chicago, Illinois in 1892. Image source.
Bird's-eye-view of the business district of Chicago. Poole Brothers, c1898. Image source.