When you read this, I have no idea what the weather will be like.

Maybe it’ll be snowing. Maybe it’ll be sunny. Maybe it’ll be warm enough to take a stroll.

I do know that these four books offer a thoughtful and expansive introduction to Chicago’s built environment. You can slip them in your bag or just carry them around with you as you wander through the city. I think of these books as providing answers to the immediacy of the world in the city’s 77 community areas as we think about their development in the past and how we might envision them in the future.

I hope they will be the start of a marvelous conversation between you and the city.

Terminal Town: An Illustrated Guide to Chicago’s Airports, Bus Depots, Train Stations, and Steamship Landings, 1939-Present, by Joseph P. Schwieterman

When I first came to Chicago more than 25 years ago, I pulled together three different resources to triangulate the exact location of the Baltimore and Ohio’s Grand Central Station at Harrison and Wells. My curious obsession with this imposing structure dated back to when I learned that it was the first home to the 20th Century Limited, sometimes known as the “World’s Greatest Train.” As I walked up to the vacant lot, I realized I was two decades too late. It was torn down in 1971. Maybe I was better off for its absence, given that my quest also led me to wander a bit more around Printers Row.

Today’s transit fans can just pick up this gracefully illustrated compendium and make their way through the past, present, and future of Chicago’s transportation venues. The train station coverage is uniformly excellent and one can read about the litany of plans introduced during the 20th century to consolidate service from six Loop stations to a solo megacomplex for both intercity and commuter trains. The appendices include nice riffs on the “Terminals of Tomorrow,” including thoughts on the proposed south suburban airport, Vertiport Chicago, and the bungled Block 37 superstation, arguably Chicago’s most expensive publicly financed hole-in-the-ground.

I just wish that the book included Louis Sullivan’s famed remark on the long-gone Illinois Central’s Central Station: “Why does not the Lake engulf it? Why does not the fire from Heaven consume it?” When I first read this as a teenager, I was struck by the intensity of his prose—and his hatred.

Forty-seven years after Sullivan died, Central Station was demolished. You can find what’s left of it in the grassy expanse south of the Grant Skate Park. I’m guessing you might be disappointed by what you find.

At Home In The Loop: How Clout and Community Built Chicago’s Dearborn Park, by Lois Wille

If you wander into Dearborn Park from State Street, it feels like a neat and tidy urban enclave, set apart from the rest of Chicago. These placid surroundings do not give any indication of the intense fracas that led to this planned community’s creation. Forty-five years ago in this area, one could have encountered a largely quiet rail yard, a crumbling Romanesque train station and light industrial detritus.

Wille takes us on a tour through the wrangling over the site’s status in the 1970s with a cast that includes George “Papa Bear” Halas, Richard J. Daley (naturally), and Mr. Mag Mile, Arthur Rubloff. If you’ve ever wondered why major urban redevelopment projects take so damn long, this book is a master class in such matters. Its story seems even more relevant today given the ongoing conversation about the proposed The 78 development just a short walk away from Dearborn Park.

Chicago 1910-29: Building, Planning and Urban Technology, by Carl W. Condit

If you approach a friend and say, “Hey, I just read this great book about urban infrastructure,” he or she may offer a perfunctory grimace or maybe a gentle nod of the head. This book may bring those folks over to the other side of bridges, tunnels, master plans, and the grandeur that was Navy (formerly Municipal) Pier.

In six thoughtful and well-arranged sections, Condit takes readers through the basics of the Chicago Plan of 1909, which would eventually bring us the Magnificent Mile and iconic cultural institutions such as the Field Museum and Shedd Aquarium. The footnotes to each chapter provide openings to various research wormholes for interested parties who want to learn more about the Lindbergh Beacon that graced the top of the Palmolive Building or the complex engineering that makes the water circulate at the Shedd Aquarium.

Old Chicago Houses, by John Drury

In his foreword, Drury asks a number of questions that animate those of us who are fascinated by residences, historic or otherwise: “Who built the house? Was its builder someone of importance in the past? When was it built? . . . Who lives in it now?”

The book originated as a series of columns in the Chicago Daily News in which Drury wandered from Norwood Park to Englewood to chronicle almost 100 homes. What could have been a deadly dull recitation of dates, architects, and accumulated fortunes turns into a lively look at these structures.

One of my favorite stories is Drury’s visit to the very tiny Henry C. Work home near 53rd and Dorchester in Hyde Park. Work is known today primarily as a composer of Civil War ditties such as “Marching Through Georgia.” As Drury approaches this Lilliputian structure, he notes, “As viewed today, the cottage hardly looks big enough to house a piano.”

And if you wander by today with Drury’s book in hand?

You’ll find that the Work cottage abides, but there is now a much larger wood house tacked on to the front of the building.   v