SOME SOURCES: 

Historic Illinois from the Air by David Buisseret (1990) ISBN: 0-226-07989-9

https://archive.org/details/historicillinois0000buis/mode/2up  is one of my favorite books and my general background for most Illinois history. It is a simple and understandable digest that covers everything from "General

Topography" to "The Atomic Era". It has facing pages on a subject with a text overview and examples with captioned images and maps. Each one is sort of free-standing, you can bounce around. An excellent starting place.

Internet Archive/Wayback Machine https://archive.org/ is an on-line library. It's free, all you need is an email address and a screen name. If they have a book you can "Borrow" but not download it.

United States Geographic Survey (USGS) has maps of the whole country. They are often revisions of earlier maps and are marked with their first and revised dates. I think they update add pretty quickly but they don't delete very fast. This is especially true for railroads, it's hard to tell  active vs. abandoned from the air. The Chicago area is here: https://ngmdb.usgs.gov/topoview/viewer/#8/41.825/-87.762 

Illinois Historical Aerial Photos (IHAP) from 1938-1939 and 1962-1967 are great: https://prairie-research.maps.arcgis.com/apps/webappviewer/index.html?id=a251e0a92bd84f978e46a0b2f3b5a50f  

DuPage County property tax maps https://gis.dupageco.org/parcelviewer/index.html?find=9912345678 

Cook County property tax search: https://www.cookcountypropertyinfo.com/default.aspx   

Google Maps satellite view has 3D with a (free) Google account. 

Google Earth Pro shows satellite views from 2000 to the present. It's a free download to a desktop from the sixteen squares in the upper right corner of any Google page. 

I DO NOT TRUST GOOGLE AI!

Sanborn Fire Insurance Maps are building by building with details from around 1900-1925 (they get updated so they are often newer than the original printing date). To get them search "city state sanborn" ("batavia il sanborn") and the Library of Congress or University of Illinois will help you out on most (not all) cities. Try U. of I. first, they download better. 

Arcadia Publishing has a bunch of 128-page booklets about individual suburbs or themes. They are a formula with the same sections in order, you would probably buy one of your individual suburb or interest. I think the good stuff is the photos with long captions.

DU PAGE COUNTY

History of DuPage County (1857)  http://livinghistoryofillinois.com/pdf_files/History_of_DuPage_County_Illinois_1857.pdf

Portrait of DuPage (1894)  https://www.elahistoricalsociety.com/portrait_and_biographical_record_of_dupage_county.pdf 

DuPage County Guide (1948)  https://dn790009.ca.archive.org/0/items/dupagecountydesc00writrich/dupagecountydesc00writrich.pdf

Pioneer Railroad (1948) (about the Northwestern):  https://libsysdigi.library.uiuc.edu/OCA/Books2010-10/pioneerrailroads00case/pioneerrailroads00case.pdf

Little Railroad Town (West Chicago City Museum class)  https://static1.squarespace.com/static/5400b8f0e4b040ba034d5c68/t/5a2aee6a085229769d8eb67e/1512763020666/Railroad+History+-+Indian+Knoll.pdf

Illinois Cities and Villages Act (1878)  http://livinghistoryofillinois.com/pdf_files/Laws%20of%20Illinois,%20Relating%20to%20Cities%20and%20Villages.pdf

CANALS

Illinois And Michigan Canal National Heritage Area by the National Park Service:  https://www.nps.gov/places/illinois-and-michigan-canal-national-heritage-area.htm

Chicago Sanitary and Ship Canal by Historic American Engineering Record (HAER)(2009)  https://tile.loc.gov/storage-services/master/pnp/habshaer/il/il0900/il0976/data/il0976data.pdf 

HistoricBridges.org (Illinois):  https://historicbridges.org/map_ill.php

Illinois and Michigan Canal by David A. Belden (2012) ISBN:978-0-7385-8297-9 is an Arcadia book.

Canal Boats along the Illinois and Michigan Canal by Floyd Mansberger and Christopher Stratton (1998)  https://illinoisarchaeology.com/IDNR/Canal%20Boats%20FRR.pdf 

National Museum of the Great Lakes:  https://nmgl.org/ 

Wisconsin Maritime Museum: https://www.wisconsinmaritime.org

Naval-Encyclopedia.com/ 

ShipBuildingHistory.com 

GreatLakesShips.com