Chicago’s Skid Row

1 Posted by - December 1, 2014 - Vintage View

Chicago’s former Skid Row is a big subject.  From its beginnings around the turn of the last century to its demise by the 1980s, there is much to be said of life amid the squalor of West Madison Street.

A Personal Perspective

When I visited Chicago (from Milwaukee) in the early 1980s with my husband, we explored parts of the city most tourists wouldn’t see.  Because he had gone to college in Chicago, he knew a city beyond the tourist zones.  We explored Uptown where he had worked at a runaway shelter.  We drove past Cabrini Green.   And we drove through what was left of Skid Row.  I remember being shocked and saddened by the down-and-out men lining the streets.

Fast forward to today.   Leading some architecture tours on a Chicago River boat, I felt compelled to mention Skid Row as we glided along the South Branch, past the glass and steel office towers that have replaced the derelict area.  I had done a little research and found that Time magazine discussed Chicago’s Skid Row in 1949, calling it “Land of the Living Dead” – and I used that phrase in my tours.

Chicago Daily News Exposé

I recently located the Time article.  It is actually the story of how the Chicago Daily News found a good story in Skid Row.   Time leads off with: “Along West Madison Street, within sight of the handsome Daily News skyscraper, sprawls the noisome slum of saloons, hash-joints, missions and flophouses that Chicago calls Skid Row. One morning last June, as he picked his way to work through Skid Row’s reeking garbage and broken bottles, and stepped past the bodies of sleeping derelicts on the sidewalks, Daily News Managing Editor Everett C. Norlander felt his stomach turn over. His next reaction was that he was walking through a good story.”

Norlander sent two young “rewrite” men to live as “bums” in order to write an exposé.   Bill Mooney and Fred Bird spent two weeks on Skid Row.  “In the twelve-part series, Reporters Mooney and Bird described the worst of 82 squalid saloons in three-quarters of a Madison Street mile (most of them selling the “morning special,” a double shot of whisky for 18¢), listed the names & addresses of saloonkeepers who were breaking the state liquor and health laws, and put the finger on couldn’t-care-less cops. The reporters took their readers on a guided tour of 46 flophouses, where 12,413 bums slept in lousy cubicles for 50¢ or 60¢ a night. They watched hard-faced jackrollers stripping the pockets and stealing the shoes from sodden bums, saw prostitutes plying their trade amid the lumber piles and back alleys, found that ‘a surprisingly large number [of derelicts] at one time were trusted employees, executives or professional men.'”

The story shocked Chicagoans, prompted a crackdown on the area…and boosted circulation of the Daily News by 20,000 copies a day.

Photograph of Madison Street, 1973, Alan Parr; current site of Presidential Towers.


  • Shawn December 1, 2014 - 4:10 pm Reply

    The 15 cent shot of whiskey blows my mind. Thanks for posting where the photo was on Madison st. Didn’t realize how close it was to the loop.

  • Wendy December 1, 2014 - 4:16 pm Reply

    I found this pretty mind-boggling, too. Thanks for your comment, Shawn.

    • John Robert Bland October 15, 2016 - 1:33 pm Reply

      Hello Wendy
      I know Sid Row well. We lived at 1906 w. Monroe when I was starting elementary school and then to Henry Horner. I walked with my friends through Skid Row. We got our hair cut at the barber college and we were daring enough to go and watch movies there. It was a sad place. I am writing a children like book and would like to get permission to use one of your photo street view of Skid Row around the mid sixties. Will give credit in book. Thank you.

      • Wendy October 16, 2016 - 5:35 am Reply

        Hi, John – your book sounds interesting. The photo I use here has no photographer cited and is circa 1973.

        • Alan January 31, 2021 - 6:57 pm Reply

          Hi Wendy! I am the photographer of this image. I know it’s a bit late for a response but I stumbled onto your site just today. Very interesting site indeed!
          Take Care,
          Alan Parr

          • Wendy January 31, 2021 - 7:02 pm

            Thank you, Alan! You mean the 1973 liquor store photo? I am sorry that I didn’t have your name – and couldn’t find it – when I chose this photo. I will attribute it to you now.

    • Laurel August 25, 2019 - 8:12 pm Reply

      Hi Wendy,
      I was a student at Moler Barber College on Clark Street at Chicago Ave in 1976-1977. That was pretty skid row-like then

      • Wendy September 1, 2019 - 11:27 am Reply

        Thanks for sharing that, Laurel. You must have some interesting memories.

  • Donna Primas December 4, 2014 - 9:40 am Reply

    When working on my master’s degree 1979-1980, I frequently walked from Ogilvie Station to classes at the University of Illinois Circle Campus in my combat boots and faded bib overalls past men sleeping in doorways. I am glad to see how things have changed.

    • Wendy December 4, 2014 - 9:51 am Reply

      I love the combat boots! Thanks for sharing that, Donna.

  • Steve Wylder August 9, 2015 - 12:51 pm Reply

    As a 15-year-old high school student, I saw Skid Row from the Madison bus after a pilgrimage to the SDS headquarters. The area has certainly gone upscale, but the down-and-out are still with us. The Single Room Occupancy hotels are completely gone from West Madison, and few remain in Chicago as a whole. At least the SROs gave a modicum of safety to the homeless.

    • Wendy August 9, 2015 - 1:08 pm Reply

      Thank you for sharing that, Steve. So true.

  • John Robert Bland October 15, 2016 - 1:26 pm Reply

    My friends and I would walk through Skid Row from downtown back to Henry Horner Homes. It was a very depressed place and all I remembered were white men. Once before I knew what a hooker was, I saw one of those men walk down to the 2000 block of Madison where this black lady was standing in the doorway of an apartment building. He went inside the doorway with her and came out within seconds and I stood near wondering what happened. Author of Urban Removal Westside Chicago. @JRBland_Author

    • Wendy October 16, 2016 - 5:33 am Reply

      Wow, John, quite a memory. Thanks for sharing that.

  • Pam D. March 4, 2017 - 10:32 pm Reply

    I just happened across this page. I have been trying to help my friend learn more about her biological father who up and left the family around 1959/1960. She just received his death certificate and it listed 66 West Buren Street as a last known address. He died on Oct 17, 1985 at University of Illinois Hospital in Chicago. How would a person find out what was at that address during this time period. It appears to be parking complex area now. At one time in the early 1900’s – it was the location of the Vestibule Hotel. I am just wondering if her father was on skid row and what this address was in 1985. Any information would be helpful on that location would be great.

    • Wendy March 13, 2017 - 10:59 pm Reply

      Hi, Pam – How kind of you to help your friend. I did some research and couldn’t come up with much on that address, except the following from RootsWeb – Irish In Chicago archives. Nan Brennan, who seems like a Chicago expert, replies to a question as to if 66 W Van Buren was technically in Skid Row? She replies:

      “That’s an interesting question, Ed.
      And I’ll look forward to reading input from others on our list. To me, Van Buren has always been a strange street. A sort of dividing line in away. 66 west Van buren, in 1930, would have been one of many SROs on that
      street, probably mostly filled with the working poor, laborers, and visitors and transients in need of inexpensive housing, as well as the unemployed. It was in 1930 and is at the south end of “the Loop” and on the fringe of the Chicago Finanical district amid a lot of office buildings. It was in 1930 and is amid and within a block or two of many great Chicago Institutions and Architecturally significant buildings: the old Federal Building, the Monadnock Building, the Chicago Board of Trade, the Art Institute of Chicago, many exclusive private clubs, the Standard Club, Chicago Athletic Association, etc, Roosevelt University, DePaul University, The Conrad Hilton Hotel (Old Stephens
      Hotel), the Rock Island Railroad LaSalle St Station, the Auditorium Theatre. It was a short walk-less than two blocks- to Grant Park, a beautiful park on Michigan Avenue and a couple more blocks east to Lake Michigan. But immediately south of Van Buren on State St in the 1930s, it would have been a bit honky tonk: cheap theatres, arcades, burlesque clubs, poolhalls, I think some vaudville, too. etc.—a vice district and I think it remained so thru the forties, maybe into the fifties. It was fringe…….on the fringe of wealth and culture and on the fringe of skid row. Nan”
      Pam, I would add that that immediate area was beginning to change with the 1970s addition of the Metro Correctional facility across the street, and in the mid-1980s with the development of the new Chicago library center nearby…but that it probably still retained its SRO-on-the-border character at the time of his death. I am guessing, but think that parking structure would have replaced the old Vestibule Hotel in the late 1980s. Hope that helps a little. Wendy

  • Pam D. March 13, 2017 - 11:17 pm Reply

    Thank you so much – yes, this is helpful. I appreciate your response so much.

  • TinoGon August 23, 2017 - 7:12 pm Reply

    For more vivid description of skid row Read Willard Motleys novel: Knock on any Door, and Let no man write my Epitaph, both of which were made into major motion pictures starring Humphrey Bogart.

    • Wendy August 24, 2017 - 5:39 am Reply

      Thank you for that, TinoGon!

  • Deidre Oliver October 22, 2017 - 5:42 am Reply

    My husband and I were talking last night about Skid Row he works up north on Wilson near Broadway and thought that that was Skid Row. I told him no, that Madison Street was.

    • Wendy October 23, 2017 - 8:11 pm Reply

      Thanks for your comment, Deidre. I think many places were named so in a casual way, but THE Skid Row in Chicago was Madison, no doubt about it.

  • Dale Edwards April 21, 2018 - 11:44 pm Reply

    Hi Wendy! My name is Dale Edwards, and I live in Grand Rapids, Minnesota! Recently, through and with the help of a friend of ours who works for Ancestry , we were able to find the last known address of our father, whom myself and my four siblings barely knew! Our Dad died alone and with no family, in 1985, and we found he lived at the Vestibule Hotel, which was torn down, but which stood at 66 West Van Buren Street in Chicago, Illinois! We also found out that my Dad is buried in Homewood Cemetery! My sister visited the pauper’s grave in Chicago where my Dad was buried, atop six or seven other unknown people! My three brothers and my little sister and I would like to see any photos of the Vestibule Hotel, where my father lived when he died! We searched for photos, but to no avail! Can you help us? Thank you so much! or

    • Wendy April 25, 2018 - 6:48 am Reply

      Hi, Dale. Thanks for your comments. I will email you what (little) I know.

      • TMeisel September 18, 2018 - 3:00 pm Reply

        Hey Dale,
        I recently found out that my Grandfather lived at 66 West Van Buren Street in Chicago too. My Grandfather died in 1953 with no family around and recently found a gravesite that has someone there by the same name although he was buried with six other people…. that made me think that maybe it wasn’t him but I noticed that you said you found the same thing out about your father. Interesting…. Did you get any cool information on the vestibule hotel? Any cool pictures? I’d love for you to share if you have any more info. Thank you!

    • Wendy April 25, 2018 - 10:18 am Reply

      Thanks for sharing your book link, John.

  • TinoGon April 25, 2018 - 9:51 am Reply

    Dale, Pam, Not for nothing but it sounds like the address in question was real close to the SRO shown in the Blues brother’s movie.

  • Annelise Braun February 12, 2020 - 6:24 pm Reply

    Interesting read here. I have been searching for my father and his relatives and I found him in Chicago 1940 Census living at 66 West Van Buren St. I would like to know more about the Vestibule Hotel where he lived as a young immigrant from Germany. Would you be so kind and share the info you shared with Dale Edwards (Apr 25, 2018) and any hints of finding more info about the Hotel etc? Thank you

    • Wendy February 13, 2020 - 2:18 pm Reply

      Thanks for your comment, Annelise. I will email you what I have.

      • Dale Edwards February 13, 2020 - 5:01 pm Reply

        Wow, Wendy! I looked at my email and saw that forward from Annelise Braun , regarding her father, a young immigrant from Germany, who had stayed at the same Vestibule Hotel that my father was living at when he died! Just hearing from someone else whose father had a common link with my Dad, made my day! Thank you so much for forwarding Annalise’s inquiry to me! I would still very much love to obtain any photo of the Vestibule Hotel at 66 West Van Buren, but so far, I haven’t been able to get ahold of a photo! I’m sure Annalise might like to see where her father lived, also, Wendy, so if in your extensive research of historical Chicago, if you ever come across a photo or any related information about the Vestibule, I would be so grateful if you could email that information to me! You’re the greatest! Thank you so very much for all you do! Dale Edwards 1413 NE 7th Avenue Grand Rapids, Minnesota 55744 and

        • Faustino February 13, 2020 - 5:45 pm Reply

          Not for nothing but that address you refer to is pretty close to the flop house that was used in the Blues Brother’s movie. Check it out.

          • dale edwards February 14, 2020 - 10:45 am

            Thanks so much, Faustino! I have tried to find a few videos associated with the Blues Brother movie and plan to keep looking through them a little more closely to see if I can spot anything resembling the Vestibule Hotel! ( not that I really know exactly what it looked like ) but it should have been on the corner of the block, if I’m not mistaken! I was actually a bit surprised that, somewhere, there wouldn’t have been a photo of the Vestibule, readily available, but that was certainly not the case! All of you people associated with ” Wendy City ” have sure been gracious and great, in responding to all the inquiries from us people out here that you don’t even know! Thank you so much, Faustino, and everyone else! As I told Wendy, ” You’re the greatest! ” Dale Edwards

        • Wendy February 14, 2020 - 9:40 am Reply

          Thank you, Dale, for your lovely comment! Nice to be among people on the same search.

  • Kristy Shubert-North February 2, 2021 - 11:00 pm Reply

    This article is so interesting. My grandfather lived on skid row in the 1940’s. I’ve been searching for him for years and found him in the Beverly Cemetery. I have so many questions.

    • Wendy February 4, 2021 - 11:07 am Reply

      Thanks, Kristy. That must have been so exciting to finally find your grandfather.

  • Dennis Lohr August 30, 2021 - 7:13 pm Reply

    While the Time article is somewhat interesting, I’m certain we could gather much deeper insights by reading the actual series in The Chicago Daily News. Unfortunately, the microfilm and online archives for The Daily News are neither easily accessible nor continuous at this point, which makes research fairly difficult outside of Chicago.

    One alternative is a similar 4-part series featuring a single reporter embedded in Chicago’s skid row and published by The Chicago Tribune from June 5th – 8th, 1960. I’ll allow others to draw their own conclusions, but the series is unsurprisingly very out-of-date with our current understanding about addiction, mental illness, and poverty.

    With that, it’s useful to provide a bit of context: It wouldn’t be until the mid- to late-1970s that alcoholism was viewed as a treatable medical condition. Prior to that time, alcoholics were largely seen as morally weak and their actions as criminal. As a point of reference, think about town drunk Otis from the Andy Griffith Show, or John Wayne’s alcoholic sidekicks played by Dean Martin in “Rio Bravo” and Robert Mitchum in “El Dorado”.

    So even the Hollywood sheriffs were incarcerated while drunk in small town America, and that last part is important: Otis wasn’t allowed to be drunk in public if it was Mayberry, but he and his peers were allowed to stumble, stagger, and pass out nearly at-will if it occurred in the bowery or skid row sections of Chicago, New York, or LA. If they were to venture outside the recognized bounds of skid row, then they were either locked up and/or driven to the edge of town.

    For those who are seeking a bit more understanding about the lives of Chicago’s skid row residents, I’d encourage you to locate “The Liquid Cross of Skid Row” by Chicago Times sportswriter William Francis Gleason (Bruce Publishing, Milwaukee, 1966). I believe there was only a single printing so it’s long since out-of-print, but used copies regularly appear for less than $20.

    The book is light reading and a highly fictionalized account of several skid row residents, as seen through the eyes of skid row missionary Msgr. Ignatius D. McDermott aka “Father Mac”. While clearly sanitized and taking some poetic license to provide simple outcomes, I did find it useful. The books offer an otherwise unavailable understanding about the mores, lifestyle, and reasons why people ended up—and remained until they died—in the flophouses along Madison Street.

    While I don’t have the ability to detail everything I’ve learned from my own research, there are several generalizations that can be made (in light of other knowledge) about those with questions about their family members:

    (1) As alluded to previously, most people ended up in skid row because they were not tolerated by society (and therefore the law) outside of skid row. They could therefore either be confined to skid row, or go to jail.
    (2) Because there was no known cure for alcoholism, residents were unlikely to ever break free from their addiction. They could not leave and could not find sobriety, so most never left and would die there.
    (3) To paraphrase, Chicago’s skid row was described as “the most womanless place on Earth”; that women were not only few and far between but those who did live there could easily be confused as being men. For some it was a defense by their own choosing, for others it was a result of the hard life they faced, and for still others it was a bit of both.
    (4) A room for the night was generally viewed as more important than liquor. The reason is because so-called “jackrollers” would prey upon those who slept or passed out in the street. They would take what little money an incapacitated man had, along with his shoes which could be sold to a used clothing store for 10-25 cents, and most importantly his social security card to claim his benefits.

    One interesting footnote is that family members would sometimes be contacted that their father, son, or brother was found deceased in skid row. Upon viewing the body, the grieving relative was shocked to discover it was actually another person.

    At some point, the deceased man had either jackrolled or otherwise gotten ahold of another man’s SSI card. And because men on skid row had very few items beyond an SSI card to identify them, it was an easy and frequent mistake to be made. In other cases, it was even more confusing because a person may be found with one or more SSI cards, using all of them to claim multiple benefits at the start of each month.

    Finally, families want to believe that some good became of their family member in the end, so a common tale is that the body was donated to science or a medical school. This rarely, if ever, was the case. The State of Illinois actually had a program for the embalming and burial of indigents. In actual fact, donating a body is/was a formal legal process that requires pre-planning, and is not something that happens to unclaimed bodies or indigents.

    I sincerely wish all of you the good health and happiness that so many of our relatives on skid row were never able to obtain during their lifetimes.

    • Wendy August 31, 2021 - 8:51 am Reply

      Thank you for all of that, Dennis!

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