Destinations, Illinois, North America

Growing Up In Chicago, IL

When I was young, maybe 8 or 9-years-old, I was in the backseat of my Dad’s car driving through downtown Denver. We were looking for a parking spot when my dad suddenly stopped, threw the car into reverse, and parallel parked like it was nobody’s business.

“Wow, Dad! That was fast!”

“My momma didn’t raise no fool,” he said.


As an adult, I’m no longer bewildered by my father’s parallel parking abilities, but I am amazed at his ability to navigate a city.

My dad grew up on the South Side of Chicago in the ‘50s and ‘60s. He still remembers his address: 7801 South Hermitage Ave. He also recalls a remarkable amount of detail about his neighborhood, all the way down to the corner grocery store where his mother and grandmother shopped, and the park he played ball in as a boy.

What kinds of things did you do for fun as a child in Chicago?

I really enjoyed playing baseball. Unfortunately, we didn’t have many organized sports. The neighborhood boys would come together and organize pick-up games. We learned most sports just by playing them over and over in the alleys or the streets.

What got you started playing baseball?

At 10 years old, my neighbor Marty asked me to play baseball. He was in little league. My father didn’t know anything about sports, my Mom did, but she just didn’t know how to support me in joining an organized league. Eventually, I joined little league on my own and walked to practice and games across town. The parks were far away, so mostly we’d play in the streets or in the alley.

What was it like playing baseball in an alley?

Well, you can only hit to center field if you’re in an alley. We broke a few windows. My dad would go and fix their windows, we never got in trouble for that, he’d just fix them. Eventually we got stronger so it was harder to play in the alley. We began to practice on the high school playground on cement. We also played at O’Hallaran Park at 83rd and Wolcott and Dawes Park at 81st and S Damen Ave.

How long did you play baseball?

I played through high school and occasionally through adulthood. I organized my own softball team in high school.

What was the neighborhood you grew up in like?

It was a middle class, mostly nice neighborhood. We didn’t know any rich people, and very few poor people.

Did you and your family have any favorite restaurants?

No. Not really. Back then we would go to McDonald’s together as a family – can you believe that? We would never do that now. I remember Ashland Pizza. The pizza was dough, tomato sauce, sausage and a pile of grease. I would never eat it today. There was also a little coffee shop/café called Field’s nearby. We went to restaurants only occasionally. There was less money for that then.

Was there a movie theatre?

Highland Theatre Chicago
Phot credit: R8teco

Yes, Highland Theatre. We walked to it from our house. In the early 1960’s, we would go there on a Saturday afternoon and see science fiction movies. I remember seeing The Blob in theatres. That was considered a scary movie at the time.

Where would you grocery shop?

We had some large grocery stores. I remember Jewell Foods – that store was more modern, National Food Store, Hi-Lo; they were all within walking distance. I remember seeing my grandmother walking home with a grocery cart. We would stop what we were doing and help her with her groceries. I thought it was funny that she took the cart with her from the store – but that was the norm back then.

There were other very small grocery stores on street corners, scattered through the neighborhood. The most peculiar was a place called Tuckers at 77th and Ashland. It was a corner store with very little square footage. It was so small that the crackers, dog food and cupcakes would all be in the same section.  Thinking back on it now, there were no “convenience” stores like 7-11, though some of the stores were similar to 7-11 in size; actually, they were smaller.

National Chicago Food Store
Photo credit: John Chuckman

The South Side of Chicago is located south of the Chicago River and is larger than the neighboring North Side and West Side regions. While the South Side has had a reputation for high crime rates, the region varies in social classes and ethnic composition.

In 2016, Chicago welcomed 54.1 million tourists, and the city expects this number to continue to rise. On our most recent trips to Chicago, we enjoyed the following attractions:

Cloud Gate (also known as The Bean)

Arguably the best place for a selfie in the city, Cloud Gate is a must-see for Chicago visitors. This attraction is located in Millenium Park and is free to visit. Plan on getting here early to avoid the crowds. Cloud Gate Chicago

Connie’s Pizza

Connie’s Pizza is my dad’s go-to when he wants a taste of nostalgia. This family owned restaurant is the first place we stop for a good, authentic, Chicago style deep dish pizza.

Connie's PizzaNavy Pier

Our favorite place to go for a stroll is Navy Pier, along the shoreline of Lake Michigan. The pier features restaurants, bars, shops and a handful of carnival rides. I remember grabbing frozen yogurt here as a child and thinking the area was pretty magical. (Navy Pier was the original site for the University of Illinois – Chicago campus, which is now located elsewhere in the city on several square miles.)

360 Chicago

What was once the John Hancock building is now 360 Chicago and features a panoramic view of downtown and Lake Michigan. Order an espresso from the Cafe and enjoy gorgeous views from the 94th floor.

Architecture Boat Tour

To this day, one of my favorite things we did while in Chicago was the architecture boat tour (I don’t remember the company we toured with, see a similar tour here). I’m not even a big architecture buff, but this tour highlighted all of the interesting buildings on the Chicago skyline and offered a new perspective of the city. I highly recommend this!


Chicago is a pretty magnificent city. My father has an impressive memory of what it was like in the ’50s and ’60s in the South Side of Chicago, and is still able to navigate the entire Chicago area with ease.

If you have questions about the area, or felt a sense of nostalgia while reading this, please reach out in the comments below, I’d love to hear from you.

Check out my other Growing Up In blogs including, Growing up in Chelmsford, MAGrowing Up In Boulder, CO, Growing Up In Flint, MI, Growing up in Westminster, CO and Growing Up In Auberry, CA.

Thanks for reading,


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