2 min read

Grandma Chicago is my Grandma.

A Chicago legend in thick socks and gym shoes.
Grandma Chicago is my Grandma.
Courtney Jolliff with 57th Street’s Grandma Chicago.


If you walk through the 57th Street viaduct in Hyde Park, there’s a mural there featuring important local people who all come with stories – and one of the people you’ll see is Grandma Chicago. My family discovered that image of Grandma Chicago on the pillar after her passing, and it really put a smile in our hearts. That’s because Grandma Chicago was my real grandma.

Grandma Chicago never met a stranger. What that means is that she made a point to speak to every person passing by her in Chicago every day. She had a book of jokes she would tell you and people would remember her. That’s how she got the name, because she kind of was Chicago. She was very close to Richard Daley when he was the mayor – they had a good working relationship and a friendship.

At the viaduct, since we discovered the piece, I’ve visited it every week, kind of like it is a gravesite. I filled in the image of my grandma with coloring, text, and the crown to put some more flair to it. She would always wear those really thick socks with gym shoes as she was traveling all over Chicago. She would try to steal mine and my brother’s gym shoes! Nikes and Jordans were her favorite. Whoever did the mural obviously remembers her signature footwear like I do! I actually turned one of the shoes she stole (haha) from my brother into a Hood Trophy, giving her roses, because she was widely known as a civil rights activist and leading Chicagoan. 

I also remember that when President Obama had his second win, there was a blizzard out and she took a bus and a train to get there against my and my uncle’s wishes. She said to us, “No, I’m going, because this is history.”

Courtney Jolliff with original works paying homage to Grandma Chicago.

I love that the image of Grandma Chicago is right at the Metra line because my first memory of her is meeting her when she was getting off the Amtrak train in Michigan to visit us when I was a kid. We took so many train rides together including from Michigan to Chicago. Having that image by the train is a sign from her to the family that she is still with us, guiding us along the track, coming and going with all the people. That feeling of the track is like a feeling of destiny about your life.

– Courtney Jolliff

P.S. Hey, remember you can contact me if you want to see more of or purchase my original works.