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Streetwise Chicago: A History of Chicago Street Names

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Book by Don Hayner, Tom McNamee

153 pages, Paperback

First published October 1, 1988

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About the author

Don Hayner

6 books1 follower
Don Hayner is the retired editor-in-chief of the Chicago Sun-Times. During his tenure as managing editor and editor, the Sun-Times was awarded multiple national and local awards for investigative reporting and breaking news, including the Pulitzer Prize for Local Reporting in 2011. Hayner is the co-author, with Tom McNamee, of Streetwise Chicago: A History of Chicago Street Names, The Metro Chicago Almanac: Fascinating Facts and Offbeat Offerings about the Windy City, and The Stadium: 1929–1994, The Official Commemorative History of the Chicago Stadium. Hayner is a graduate of Ripon College and John Marshall Law School.

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Displaying 1 - 6 of 6 reviews
Profile Image for Kaesa.
251 reviews18 followers
June 26, 2021
This is maybe the nerdiest Chicago book I've ever read??? Wait, no, there was that history of Chicago zoning, never mind. This is up there, anyway. That said, it was really interesting to find out some of the histories behind streets I've lived on and am familiar with -- and it wasn't very interesting, in some cases. (I used to live on Dakin, which I assumed was named for a developer or something, and I was right.) Oddly current, too; recently they've announced the renaming of Lake Shore Drive, and I was surprised to find that this kind of thing has happened before -- Crawford Avenue was renamed largely for political reasons to Pulaski Road in 1952 after nineteen years of legal battles because the people who owned businesses on it did not want to have to change their stationery. So while I'm rolling my eyes at the LSD renaming (we could save so much money by dealing seriously with our city's actual problems with, say, racist cops, for example) I'm also rolling my eyes at the people who are up in arms about ~political correctness gone mad~ because in seventy years, no one will remember or care.
Profile Image for Steven.
39 reviews1 follower
September 12, 2025
A gloriously nerdy, well-researched reference guide to the etymologies of Chicago street names. Apart from a short foreword, preface, intro, and appendix, it presents each street name alphabetically with its etymology, if known. Predictably, a lot of them are named after powerful historical figures, rich real estate developers, and their families, but there’s enough variation to keep things interesting.

Some of my favorite fun facts:
- The “boundary” streets of North Avenue (1600 N) and Western Ave (2400 W) used to be the northern and western boundaries of Chicago city limits in the mid-1800s

- Michigan Avenue (100 E) used to run right along Lake Michigan until land was filled in to create Grant Park

- The renaming of Crawford Avenue to Pulaski Road (4000 W) (as a political favor by Mayor Ed Kelly in 1933 to the Polish Women’s Alliance) was held up in court until 1952 when the Illinois Supreme Court ruled that property owners can’t control the naming of the street.

- The first marriage in Chicago took place between Eleanor Kinzie (whose early Chicago settler father is the namesake of Kinzie St (400 N)) and Dr. Alexander Wolcott (1900 W) in 1823.

- Rosehill Drive (5800 N) and Cemetery are named for the land owned by Hyram Roe, an 1850s tavern keeper. Roe’s Hill became Rosehill!

- Southport Ave (1400 W) — stagecoach drivers between Chicago and Milwaukee traveled this street and referred to the former as the “south port” and the latter as the “north port”.

- Sunnyside Ave (4500 N) was named for the Sunnyside Hotel at the intersection of what is now Sunnyside Ave & Clark St, a house of prostitution run by a 300-pound woman named Gentle Annie Stafford whose favorite poet was Byron.

- We have map-maker/surveyor James Thompson to thank for laying out the Chicago grid, originally bounded by Kinzie (400 N), Jefferson (600 W), Washington (100 N), and Dearborn (100 W) streets.

- The architect of Chicago’s numbering system, Edward P. Brennan, saved us from the horrid pre-1909 system where, among many other issues, address numbers on the city’s north side increased to the east, but on the south side they increased to the west.

• The new 1909 system set the origin at State & Madison and said there would be eight blocks (800) to a mile. Even numbered addresses would be on north and west sides of streets, while odd numbered addresses would be on south and east sides.

• In 1913 Brennan also got City Council to give all portions of any street one name. This fixed the problem of, for example, one street being called Green Street on one block, Lime Street on another, Dayton Street, on another, Newberry Avenue on yet another, and so on.

• A similar issue—exemplified by 1893 Chicago’s seventeen Lincoln streets, avenues, or places—was resolved gradually throughout the rest of the early 1900s as City Council renamed hundreds of street names to ensure consistency and avoid repetition.

I’m sure I’ll continue to flip through this book periodically as I get to know the city better and get curious about the origins of more street names.
Profile Image for Jane.
173 reviews2 followers
April 23, 2019
I wanted information about the city prior to 1910 for genealogy purposes. It was good.
This entire review has been hidden because of spoilers.
Profile Image for Lesley.
120 reviews59 followers
Read
July 14, 2008
booooooring. i got this book on my kick for chicago history. but it was dull and dry.
i mean i guess i should have expected it. most of the streets are named after obscure people or else for obvious things, like streets in other states from where the streetnamers were from.
no real juicy stories of street name-age to be found here.
sigh.

150 reviews
March 20, 2011
As others have noted, mostly very dry. Use a variation of : " was named for xxxx, a developer (or daughter, or wife of a developer) in the area," for eighty percent of the entries.

But there are some historical tidbits, and a really good section on how Chicago reset its old street numbering system to the one they have today.
36 reviews
February 14, 2010
The title pretty much says it all, and the book delivers what it says it'll deliver.

Eventually I'll get around to some fiction.
Displaying 1 - 6 of 6 reviews

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